Main-chain polymers, optical films, their manufacturing methods and multilayer films

Abstract

This embodiment is a main-chain polymer, which is a photoreactive reverse wavelength dispersive unit that has two functions in the polymer main chain: photoreactivity and birefringence reverse wavelength dispersibility. The aforementioned photoreactive reverse wavelength dispersive unit has the structure represented by the following chemical formula (1).

Description

Technical Field

[0001] This invention relates to main-chain polymers, compositions, optical films, and manufacturing methods. Prior Technology

[0002] Organic EL displays and liquid crystal displays (LCDs) are important display devices in the multimedia society, widely used in various smart devices, computer monitors, televisions, and more. Furthermore, these displays utilize numerous optical films to enhance display characteristics, playing a significant role in improving contrast and compensating for color tones when viewed from the front or at an angle.

[0003] Phase retardation films are a representative example of optical films used in organic EL displays and liquid crystal displays. Phase retardation films, when combined with polarizing plates, can be used as anti-reflective layers in various displays. In this application, phase retardation films with a larger in-plane phase difference over longer wavelengths are particularly needed; that is, films with inverse wavelength dispersion (hereinafter also referred to as inverse wavelength dispersion films). For example, in the case of using inverse wavelength dispersion films in circular polarizing plates for organic EL displays, the phase difference is preferably about 1 / 4 of the measured wavelength λ. Specifically, the ratio of the in-plane phase difference at 450 nm to the in-plane phase difference at 550 nm, Re(450) / Re(550), is preferably close to 0.80~0.89.

[0004] Various polymeric liquid crystal compounds with reverse wavelength dispersibility have been developed as raw materials for manufacturing reverse wavelength dispersibility films. However, in manufacturing reverse wavelength dispersibility films, these polymeric liquid crystal compounds are coated onto alignment films prepared by pre-treatment through friction or photo-alignment (e.g., see Patent Documents 1-3) or alignment films prepared by photo-alignment, and then cured by light, heat, etc., to form a film. That is, the alignment film formation step is indispensable (e.g., see Patent Document 4). In addition, polymeric liquid crystal compounds with reverse wavelength dispersibility are manufactured by multi-stage synthesis (e.g., see Patent Document 5). Furthermore, it has been proposed to use side-chain acrylate resins to form phase reversal films without the need for alignment films (e.g., see Patent Documents 6 and 7). However, side-chain liquid crystal acrylate resins containing photoreactive groups have problems such as requiring multi-stage synthesis of monomers, high cost, and low heat resistance temperature. Linear liquid crystal polyester resins containing photoreactive groups can form optical films and retardation films without the need for alignment films, and can be produced by polarized ultraviolet irradiation and heat treatment. This promises to manufacture optical films and retardation films with excellent heat resistance from inexpensive monomers. However, while linear liquid crystal polyester resins possess excellent heat resistance, they require high processing temperatures exceeding 200 degrees Celsius (e.g., Patent Documents 8-10). Therefore, when linear liquid crystal polyester resins are used as optical films and retardation films, there is a problem that inexpensive and widely used resin film support substrates, such as polyethylene terephthalate (heat resistance temperature approximately 160°C), polyethylene naphthalate (heat resistance temperature approximately 200°C), and cycloolefin polymers (heat resistance temperature approximately 160°C), cannot be used.

[0005] [Preliminary Technology Documents]

[0006] [Patent Literature]

[0007] Patent Document 1: Japanese Patent Application Publication No. 8-160430

[0008] Patent Document 2: Japanese Patent Application Publication No. 2003-505561

[0009] Patent Document 3: International Publication No. 2010-150748

[0010] Patent Document 4: Japanese Patent No. 6172556

[0011] Patent Document 5: Japanese Patent No. 6754845

[0012] Patent Document 6: Japanese Patent Application Laid-Open No. 2002-226858

[0013] Patent Document 7: Pamphlet of International Publication No. 2014 / 017497

[0014] Patent Document 8: Japanese Patent Application Laid-Open No. 2018-188529

[0015] Patent Document 9: Japanese Patent Application Laid-Open No. 2021-028375

[0016] Patent Document 10: Japanese Patent Application Laid-Open No. 2021-028384 Summary of the Invention Problems to be Solved by the Invention

[0017] As described in the above background art, in the case of using a polymerizable liquid crystal compound having inverse wavelength dispersion as a raw material for manufacturing an inverse wavelength dispersion film, the step of forming a liquid crystal alignment film is indispensable, and it is hardly advantageous in the manufacturing process of the inverse wavelength dispersion film.

[0018] In addition, the polymerizable liquid crystal compound having inverse wavelength dispersion used as a raw material for manufacturing an inverse wavelength dispersion film often requires multi-step synthesis, and the economy is poor.

[0019] Therefore, in the present invention, it is an object to provide an inverse wavelength dispersion film that does not require the step of forming an alignment film and can be formed by coating a polymer, and this has been studied. Means for Solving the Problems

[0020] As a result of intensive studies to solve the above problems, the present inventors have found that by using a resin composition containing: a polymer having a specific photoreactive structure exhibiting birefringent inverse wavelength dispersion, a photoreactive inverse wavelength dispersion unit (hereinafter, sometimes also referred to as photoreactive inverse wavelength dispersion unit A or unit A) exhibiting the two functions of photoreactivity and birefringent inverse wavelength dispersion, a polymer having a specific photoreactive group, and a specific additive, an inverse wavelength dispersion retardation film can be formed without an alignment film, and thus the present invention has been completed.

[0021] The present invention is proposed based on such an idea, and specifically has the following constitution. <​A main-chain polymer having a photoreactive reverse wavelength dispersive unit within the polymer main chain that exhibits both photoreactivity and birefringence in reverse wavelength dispersibility, wherein the aforementioned photoreactive reverse wavelength dispersive unit has the structure represented by the following chemical formula (1).

[0023] [Chemistry 1]

[0024] In the aforementioned chemical formula (1), L1 and L2 may be the same or different, representing carbonyl, ester, amide, ether or single bond.

[0025] * indicates the bonding position with other structures in the aforementioned main-chain polymer.

[0026] Ar represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are designated as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, or condensed aromatic rings may have substituents.

[0027] R0, R1, R2, R3, and R4 independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1).

[0028]

[0029] In the aforementioned chemical formula (Z1), Rz3 and Rz4 independently represent hydrogen atoms, halogen atoms, or alkyl groups with 1 to 8 carbon atoms, respectively.

[0030] Arz represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are defined as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, or condensed aromatic rings may have substituents.

[0031] The wavy part represents the bond position of the part other than R0, R1, R2, R3, or R4 in equation (1).

[0032] A dihydroxy compound represented by the following chemical formula (1').

[0033]

[0034] [In the aforementioned chemical formula (1'), R0, R1, R2, R3, and R4 independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1). Ar represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are designated as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, or condensed aromatic rings may have substituents.]

[0035]

[0036] In the aforementioned chemical formula (Z1), Rz3 and Rz4 independently represent hydrogen atoms, halogen atoms, or alkyl groups with 1 to 8 carbon atoms, respectively.

[0037] Arz represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are defined as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, or condensed aromatic rings may have substituents.

[0038] The wavy line represents the bond position with respect to the portion of equation (1) other than R0, R1, R2, R3, or R4.

[0039] A method for manufacturing a dihydroxy compound, comprising reacting a dihydroxy compound represented by the following chemical formula (3) with a ketone represented by the following chemical formula (4') to obtain a dihydroxy compound represented by the following chemical formula (1').

[0040]

[0041] In the aforementioned chemical formula (3), R0, R1, and R7 independently represent hydrogen atoms, halogen atoms, or alkyl groups with 1 to 8 carbon atoms.

[0042] R2f represents a hydrogen atom, a halogen atom, an alkyl group with 1 to 8 carbon atoms, or a methyl group.

[0043]

[0044] In the aforementioned chemical formula (4'), R8 represents an alkyl group having 1 to 8 carbon atoms, or a haloalkyl group having 1 to 6 carbon atoms.

[0045] Ar represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are considered as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings may have substituents.

[0046] [Chemistry 7]

[0047] [In the aforementioned chemical formula (1'), R0, R1, R2, R3, and R4 independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1). Ar represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are designated as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, or condensed aromatic rings may have substituents.]

[0048]

[0049] In the aforementioned chemical formula (Z1), Rz3 and Rz4 independently represent hydrogen atoms, halogen atoms, or alkyl groups with 1 to 8 carbon atoms, respectively.

[0050] Arz represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, and a condensed aromatic ring, wherein atoms selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom are set as the atoms constituting the ring, and these monocyclic aromatic rings, polycyclic aromatic rings, or condensed aromatic rings may have substituents. The wavy line portion represents the bonding position to a portion other than R0, R1, R2, R3, or R4 in formula (1). Effect of the Invention

[0051] According to the present invention, it is possible to provide an inverse wavelength dispersion film that does not require a step of forming an alignment film and can be formed by coating a polymer. Embodiment

[0052] [Mode for Carrying Out the Invention]

[0053] Hereinafter, the present invention will be described in detail. Although the constituent elements described below are described based on representative embodiments and specific examples, the present invention is not limited to such embodiments. In addition, in this specification, the meaning of using "~" is to indicate that the numerical range is a range including the numerical values described before and after "~" as the lower limit value and the upper limit value.

[0054] In this specification, the structure within the range surrounded by square brackets in the polymer structure represents the repeating unit in the polymer structure.

[0055] In this specification, the number described at the lower right of the square brackets in the polymer structure represents the content ratio of this repeating unit in the polymer structure.

[0056] In this specification, the bonding direction of the exemplified divalent groups, chemical structures, etc. (for example, ester bond, repeating unit in the polymer structure) is not particularly limited within the range allowed chemically.

[0057] One aspect of the present invention is a main-chain type polymer having a photoreactive inverse wavelength dispersive unit A that exhibits two functions of photoreactivity and birefringence in the polymer main chain (hereinafter, there are also cases where it is expressed as the polymer of the present invention).

[0058] As the photoreactive inverse wavelength dispersive unit A, the structure shown in the following chemical formula (1) can be cited.

[0059] [Chemical Formula 9]

[0060] In formula (1), L1 and L2 can be the same or different, representing carbonyl, ester, amide, ether or single bond.

[0061] * indicates the bonding position with other structures in the aforementioned main-chain polymer.

[0062] Ar represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are designated as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings may have substituents.

[0063] R0, R1, R2, R3, and R4 independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1).

[0064]

[0065] In the aforementioned chemical formula (Z1), Rz3 and Rz4 independently represent hydrogen atoms, halogen atoms, or alkyl groups with 1 to 8 carbon atoms, respectively.

[0066] Arz represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are considered as the atoms constituting the ring. These monocyclic, polycyclic, or condensed aromatic rings may have substituents. The wavy part indicates the bond position with the portion of formula (1) other than R0, R1, R2, R3, or R4.

[0067] In formula (1), R0, R1, R2, R3, and R4 independently represent a hydrogen atom, a halogen atom, an alkyl group with 1 to 8 carbon atoms, or a group represented by chemical formula (Z1); as a halogen atom, examples include chlorine atom, bromine atom, iodine atom, and fluorine atom; as an alkyl group with 1 to 8 carbon atoms, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, and octyl.

[0068] In formula (Z1), Rz3 and Rz4 independently represent hydrogen atoms, halogen atoms, or alkyl groups having 1 to 8 carbon atoms, respectively; as halogen atoms, examples include chlorine atoms, bromine atoms, iodine atoms, and fluorine atoms; as alkyl groups having 1 to 8 carbon atoms, examples include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, and octyl.

[0069] In formula (Z1), Rz3 and Rz4 are points that exhibit good optical properties with the polymer of the present invention, preferably hydrogen atom, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, second butyl, and third butyl, with hydrogen atom, methyl, and ethyl being particularly preferred.

[0070] Arz represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are defined as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings may have substituents.

[0071] In Arz, a monocyclic aromatic ring can have substituents, where atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are used as the atoms constituting the ring. Examples include benzene, pyridine, pyrazine, pyrimidine, pyridazine, furan, pyrrole, imidazole, thiophene, pyrazole, oxazole, isoxazole, thiazole, and triazole.

[0072] In Arz, atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are designated as the atoms constituting the ring. Polycyclic aromatic rings with substituents can be used, for example, biphenyl, terphenyl, bipyridine, bithiophene, and bifuran.

[0073] In Arz, atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are designated as the atoms constituting the ring. These atoms can have substituent-containing condensed aromatic rings. Examples include naphthalene, anthracene, phenanthrene, quinoline, benzofuran, benzimidazole, benzothiophene, indole, indazole, benzoxazole, benzothiazole, and benzotriazole.

[0074] As an Arz, from an easily accessible point of view, it is preferable to use atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms as the atoms constituting the ring, and to form a monocyclic aromatic ring that can have substituents. For the polymer of the present invention to exhibit good optical properties, the aromatic ring is further preferably a benzene ring, furan ring, thiophene ring, thiazole ring, or oxazole ring; and for the polymer of the present invention to further exhibit good optical properties, a benzene ring or thiophene ring is even more preferred.

[0075] As R0, R1, R2, R3, and R4, the polymer of the present invention exhibits good optical properties, preferably with hydrogen atom, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, terbutyl, or groups represented by the following chemical formulas (Z1-1) to (Z1-4), with hydrogen atom, methyl, and ethyl being particularly preferred.

[0076]

[0077] In formula (1), L1 and L2 can be the same or different, representing carbonyl, ester, amide, ether or single bond.

[0078] As L1 and L2, carbonyl, ester or ether linkages are preferred.

[0079] In formula (1), Ar represents a ring selected from monocyclic aromatic rings, polycyclic aromatic rings and condensed aromatic rings, wherein the atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms and sulfur atoms are set as the atoms constituting the ring, and these monocyclic aromatic rings, polycyclic aromatic rings and condensed aromatic rings may have substituents.

[0080] Here, examples of substituents in monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings include alkyl groups with 1 to 8 carbon atoms, halogen atoms, alkoxy groups with 1 to 4 carbon atoms, and acetyl groups with 2 to 4 carbon atoms.

[0081] Examples of alkyl groups having 1 to 8 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, and octyl.

[0082] Examples of halogen atoms include, for example, fluorine, chlorine, bromine, and iodine.

[0083] Examples of alkoxy groups with 1 to 4 carbon atoms include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, dibutoxy, and terbutoxy.

[0084] Examples of acetylated groups with 2 to 4 carbon atoms include acetylated, propionic, and butylated.

[0085] In Ar, a monocyclic aromatic ring can have substituents, where atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are used as the atoms constituting the ring. Examples include benzene, pyridine, pyrazine, pyrimidine, pyridazine, furan, pyrrole, imidazole, thiophene, pyrazole, oxazole, isoxazole, thiazole, and triazole.

[0086] In Ar, atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are designated as the atoms constituting the ring. Polycyclic aromatic rings with substituents can be used, for example, biphenyl, terphenyl, bipyridine, bithiophene, and bifuran.

[0087] In Ar, the atoms selected from the group consisting of carbon, nitrogen, oxygen and sulfur atoms are set as the atoms constituting the ring. The ring can be a condensed aromatic ring with substituents. Examples include naphthalene, anthracene, phenanthrene, quinoline, benzofuran, benzimidazole, benzothiophene, indole, indazole, benzoxazole, benzothiazole and benzotriazole.

[0088] As for Ar, from an easily accessible point of view, it is preferable to use atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms as the atoms constituting the ring, and to form a monocyclic aromatic ring that can have substituents. For the polymer of the present invention to exhibit good optical properties, the aromatic ring is further preferably a benzene ring, furan ring, thiophene ring, thiazole ring, or oxazole ring. For the polymer of the present invention to further exhibit good optical properties, benzene rings and thiophene rings are even more preferred.

[0089] As a better example of Ar, the structures shown by the following chemical formulas (Ar-1) to (Ar-7) can be listed.

[0090]

[0091] In the aforementioned chemical formulas (Ar-1) to (Ar-7), X1, X2, X3, X4, X5, X6, X7, and X8 independently represent alkyl groups with 1 to 8 carbon atoms, alkoxy groups with 1 to 6 carbon atoms, halogen atoms, nitro groups, cyano groups, alkylthio groups with 1 to 6 carbon atoms, or dialkylamine groups with 2 to 8 carbon atoms.

[0092] Re represents an alkyl group with 1 to 10 hydrogen atoms or carbon atoms.

[0093] **Indicates the bond positions with the parts of the aforementioned chemical formula (1) other than Ar.

[0094] In formulas (Ar-1) to (Ar-7), X1, X2, X3, X4, X5, X6, X7, and X8 independently represent a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a halogen atom, a nitro group, a cyano group, an alkylthio group with 1 to 6 carbon atoms, or a dialkylamino group with 2 to 8 carbon atoms; examples of alkyl groups with 1 to 8 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, and octyl; examples of alkoxy groups with 1 to 6 carbon atoms include... Examples of halogen atoms include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, dibutoxy, tributoxy, pentoxy, and hexoxy; halogen atoms include, for example, fluorine, chlorine, bromine, and iodine; alkylthio groups with 1 to 6 carbon atoms include, for example, methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, dibutylthio, tributylthio, pentoxy, and hexylthio; and dialkylamino groups with 2 to 8 carbon atoms include, for example, dimethylamino, diethylamino, dipropylamino, and dibutylamino.

[0095] For X1, X2, X3, X4, X5, X6, X7, and X8, the preferred features for the superior optical properties of the polymer of the present invention are hydrogen atoms, alkyl groups with 1 to 8 carbon atoms, alkoxy groups with 1 to 6 carbon atoms, or halogen atoms. The preferred features for easy introduction are hydrogen atoms, methyl groups, methoxy groups, or halogen atoms.

[0096] In (Ar-1)~(Ar-7), Re represents a hydrogen atom or an alkyl group with 1 to 10 carbon atoms. Examples of alkyl groups with 1 to 10 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl.

[0097] As for Re, the excellent optical properties of the polymer of the present invention are preferably hydrogen atoms, methyl groups, and alkyl groups having 1 to 4 carbon atoms, and are particularly preferably hydrogen atoms, methyl groups, ethyl groups, propyl groups, butyl groups, isobutyl groups, dibutyl groups, and terbutyl groups.

[0098] As a specific example of the photoreactive reverse wavelength dispersion unit A shown in general formula (1), the photoreactive reverse wavelength dispersion unit A shown in the following chemical formulas (1-1-1) to (1-7-4) can be listed.

[0099] [Chemistry 13]

[0100] [Chemistry 14]

[0101]

[0102]

[0103]

[0104]

[0105] [Chemistry 19]

[0106] In formulas (1-1-1) to (1-7-4), L1 and L2 can be the same or different, representing carbonyl, ester, amide, ether or single bond.

[0107] * indicates the bonding position with other structures in the aforementioned main-chain polymer.

[0108] Among these (1-1-1)~(1-7-4), the preferred ones are (1-1-1)~(1-2-11), (1-6-1)~(1-6-4), and (1-7-1)~(1-7-4), and the most preferred ones are (1-2-1)~(1-2-8) and (1-7-1)~(1-7-3).

[0109] The polymer of the present invention is preferably having at least one repeating unit selected from the group consisting of the following chemical formulas (2A), (2B), (2C), and (2D).

[0110]

[0111] In the aforementioned chemical formula (2A), ring C, ring D, and ring E independently represent rings selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings. Atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are designated as the atoms constituting the rings. These monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have substituents.

[0112] R5 and R6 may be the same or different, representing a group selected from the group consisting of hydrogen atoms, alkyl groups with 1 to 20 substituted carbon atoms, cycloalkyl groups with 3 to 8 substituted carbon atoms, and aromatic groups with 3 to 12 substituted carbon atoms.

[0113] n is 0 or 1.

[0114] L3 and L4 can be the same or different, representing carbonyl, ester, amide, ether, or single bonds.

[0115] *** indicates the bonding position with other structures in the aforementioned main-chain polymer.

[0116] In formula (2A), ring C, ring D and ring E independently represent rings selected from groups consisting of monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings and aliphatic hydrocarbon rings. Atoms selected from groups consisting of carbon atoms, nitrogen atoms, oxygen atoms and sulfur atoms are set as the atoms constituting the rings. These monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings and aliphatic hydrocarbon rings may have substituents.

[0117] In ring C, specific examples of monocyclic aromatic rings that can have substituents, such as benzene, pyridine, pyrazine, pyrimidine, pyridazine, furan, pyrrole, imidazole, thiophene, pyrazole, oxazole, isoxazole, thiazole, and triazole, are listed.

[0118] In ring C, atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are used as the atoms constituting the ring. It can be a polycyclic aromatic ring with substituents, for example, biphenyl, terphenyl, bipyridine, bithiophene, and bifuran.

[0119] In ring C, atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are used as the atoms constituting the ring. A condensed aromatic ring that can have substituents can be listed, such as naphthalene, anthracene, phenanthrene, quinoline, benzofuran, benzimidazole, benzothiophene, indole, indazole, benzoxazole, benzothiazole, and benzotriazole.

[0120] In the ring C, as a specific example of an aliphatic hydrocarbon ring that can have substituents, the atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms and sulfur atoms are used as the atoms constituting the ring. Examples include cyclopentane, cyclohexane and tricyclo[5.2.1.0(2,6)]decane.

[0121] For the ring C, the advantage is that it is easy to obtain carboxylic acids as raw materials. It is preferable to select atoms of the group consisting of carbon, nitrogen, oxygen and sulfur atoms as the atoms constituting the ring, and it is a monocyclic aromatic ring that can have substituents. The advantage is that it is easy to introduce, and benzene ring is particularly preferred.

[0122] In formula (2A), ring D and ring E independently represent the group of rings selected from monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings and aliphatic hydrocarbon rings, respectively. The atoms selected from the group of carbon atoms, nitrogen atoms, oxygen atoms and sulfur atoms are set as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings and aliphatic hydrocarbon rings may have substituents.

[0123] As for specific rings D and E, those identical to ring C can be listed independently. It is preferable to select a group of atoms composed of carbon, nitrogen, oxygen and sulfur atoms as the atoms constituting the ring in a monocyclic aromatic ring, with benzene rings being particularly preferred for ease of introduction.

[0124] Here, as substituents in monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings, examples include alkyl groups with 1 to 8 carbon atoms, halogen atoms, alkoxy groups with 1 to 4 carbon atoms, and acetyl groups with 2 to 4 carbon atoms; as alkyl groups with 1 to 8 carbon atoms, examples include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, and octyl; as halogen atoms, examples include fluorine, chlorine, bromine, and iodine; as alkoxy groups with 1 to 4 carbon atoms, examples include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, dibutoxy, and tributoxy; as acetyl groups with 2 to 4 carbon atoms, examples include acetyl, propoxy, and butyl.

[0125] In formula (2A), R5 and R6 may be the same or different, representing a group selected from the group consisting of hydrogen atoms, alkyl groups with 1 to 20 substituted carbon atoms, cycloalkyl groups with 3 to 8 substituted carbon atoms, and aromatic groups with 3 to 12 substituted carbon atoms.

[0126] Examples of alkyl groups having 1 to 20 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, and eicosyl, with methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, and tributyl being preferred. Methyl and ethyl are particularly preferred for ease of introduction.

[0127] Examples of cycloalkyl groups with 3 to 8 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.

[0128] As aromatic groups with 3 to 12 carbon atoms, examples include phenyl, naphthyl, biphenyl, and pyridyl.

[0129]

[0130] In the aforementioned chemical formula (2B), L9 and L10 may be the same or different, representing carbonyl, ester, amide, ether or single bond.

[0131] *** indicates the bonding position with other structures in the aforementioned main-chain polymer.

[0132]

[0133] In the aforementioned chemical formula (2C), X9 represents an alkyl chain with 1 to 10 carbon atoms and a single bond.

[0134] X10 represents -O- and -N(Rc)-.

[0135] X11 represents -O- and -N(Rd)-.

[0136] Rc and Rd can be the same or different, representing alkyl groups with 1 to 10 hydrogen atoms or carbon atoms.

[0137] L11 and L12 can be the same or different, representing carbonyl, ester, amide, ether, or single bonds.

[0138] *** indicates the bonding position with other structures in the aforementioned main-chain polymer.

[0139]

[0140] In the aforementioned chemical formula (2D), ring G represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, spirocyclic rings, and aliphatic hydrocarbon rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are designated as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, spirocyclic rings, and aliphatic hydrocarbon rings may have substituents.

[0141] L13 and L14 can be the same or different, representing single bonds and alkyl chains with 1 to 6 carbon atoms.

[0142] L15 and L16 can be the same or different, representing carbonyl, ester, amide, ether, or single bonds.

[0143] *** indicates the bonding position with other structures in the aforementioned main-chain polymer.

[0144] In formula (2D), ring G independently represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, spirocyclic rings, and aliphatic hydrocarbon rings. Atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are set as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, spirocyclic rings, and aliphatic hydrocarbon rings may have substituents.

[0145] In ring G, specific examples of monocyclic aromatic rings that can have substituents, such as benzene, pyridine, pyrazine, pyrimidine, pyridazine, furan, pyrrole, imidazole, thiophene, pyrazole, oxazole, isoxazole, thiazolium, and triazole, are given.

[0146] In ring G, atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are used as the atoms constituting the ring. It can be a polycyclic aromatic ring with substituents, such as biphenyl, terphenyl, bipyridine, bithiophene, and bifuran.

[0147] In ring G, the atoms that constitute the ring are selected from the group consisting of carbon, nitrogen, oxygen and sulfur atoms. It can be a condensed aromatic ring with substituents. Examples include naphthalene, anthracene, phenanthrene, quinoline, benzofuran, benzimidazole, benzothiophene, indole, indazole, benzoxazole, benzothiazole and benzotriazole.

[0148] In ring G, a spirocycle that can have substituents can be constructed by setting atoms selected from the group consisting of carbon, nitrogen, oxygen and sulfur atoms as the atoms constituting the ring. The structure shown in the following chemical formula (sp1-1) can be listed.

[0149]

[0150] In ring G, the atoms that constitute the ring are selected from the group consisting of carbon, nitrogen, oxygen and sulfur atoms. Aliphatic hydrocarbon rings that may have substituents can be listed, such as cyclopropane, cyclopentane, cyclohexane and tricyclo[5.2.1.0(2,6)]decane.

[0151] For ring G, it is preferable to choose a monocyclic aromatic ring or aliphatic hydrocarbon ring that is easy to obtain, with the group of atoms consisting of carbon, nitrogen, oxygen and sulfur atoms as the atoms constituting the ring. For good optical properties, benzene ring, cyclohexane and tricyclic [5.2.1.0(2,6)]decane are particularly preferred.

[0152] As a preferred example of the repeating unit shown in the general formula (2A), the repeating unit shown in the following chemical formula (2'A) can be listed.

[0153] [Chemistry 25]

[0154] In equation (2'A), rings C, R5, R6, L3, L4, and n are synonyms of rings C, R5, R6, L3, L4, and n in equation (2A), respectively.

[0155] As a specific example of the repeating unit shown in the general formula (2A), the structures shown in the following chemical formulas (2A-1-1) to (2A-2-20) can be listed.

[0156]

[0157]

[0158] [Chemistry 28]

[0159] [Chemistry 29]

[0160] [Chemistry 30]

[0161] [Chemistry 31]

[0162] [In formulas (2A-1-1) to (2A-2-20), L3 and L4 may be the same or different, representing carbonyl groups, ester bonds, amide bonds, ether bonds, or single bonds.]

[0163] Among these (2A-1-1) to (2A-2-20), the monomers that are easily synthesized into raw materials for the polymer of the present invention are preferably (2A-1-1) to (2A-1-10), (2A-1-36) to (2A-1-40), (2A-1-51) to (2A-1-55), (2A-1-91) to (2A-1-105), and (2A-2-1) to (2A-2-4). Among these monomers, (2A-1-1) to (2A-1-10), (2A-1-36) to (2A-1-40), (2A-1-91) to (2A-1-105), (2A-1-51) to (2A-1-55), and (2A-1-104) are particularly preferred for their superior optical properties of the polymer of the present invention.

[0164] As specific examples of the repeating unit shown in the general formula (2B), the structures shown in the following chemical formulas (2B-1) to (2B-3) can be listed.

[0165]

[0166] Of these (2B-1) to (2B-3), (2B-1) is preferred due to its superior optical properties of the polymer of the present invention.

[0167] As specific examples of the repeating unit shown in the general formula (2C), the structures shown in the following chemical formulas (2C-1-1) to (2C-2-23) can be listed.

[0168]

[0169]

[0170] [Chemistry 35]

[0171] Among these (2C-1-1) to (2C-2-23), those (2C-1-1) to (2C-1-8), (2C-2-2) to (2C-2-6), and (2C-2-13) to (2C-2-19) are preferred for their superior optical properties of the polymer of the present invention.

[0172] As specific examples of the repeating unit shown in the general formula (2D), the structures shown in the following chemical formulas (2D-1-1) to (2D-14-1) can be listed.

[0173] [Chemistry 36]

[0174] [Chemistry 37]

[0175] [Chemistry 38]

[0176]

[0177]

[0178] Among these (2D-1-1) to (2D-14-1), those (2D-1-1), (2D-2-1), (2D-3-1), (2D-7-3), (2D-7-4), (2D-7-6), (2D-8-1) to (2D-13-1), and (2D-14-1) are preferred for their superior optical properties of the polymer of the present invention.

[0179] Furthermore, the polymer of the present invention is preferably made of at least one repeating unit shown in the following chemical formulas (5-1) to (5-13) for the purpose of regulating the physical properties exhibited.

[0180]

[0181] In formulas (5-1) to (5-13), L5 and L6 can be the same or different, representing carbonyl, ester, amide, ether or single bond.

[0182] n represents an integer from 4 to 500.

[0183] *** indicates the bonding position with other structures in the aforementioned main-chain polymer.

[0184] The polymers of the present invention may also contain structures shown in the following chemical formulas (6-1) to (6-12) for the purpose of adjusting the physical properties exhibited.

[0185]

[0186] In formulas (6-1) to (6-12), L7 and L8 can be the same or different, representing carbonyl, ester, amide, ether or single bond.

[0187] *** indicates the bonding position with other structures in the aforementioned main-chain polymer.

[0188] As specific examples of the polymers of the present invention, structures shown in the following chemical formulas (P1-1-1-1-1) to (P7-12-1) can be cited.

[0189]

[0190] [Chemistry 44]

[0191] [Chemistry 45]

[0192] [Chemistry 46]

[0193] [Chemistry 47]

[0194] [Chemistry 48]

[0195] [Chemistry 49]

[0196] [Transformation 50]

[0197] [Chemistry 51]

[0198] [Chemistry 52]

[0199] [Chemistry 53]

[0200] [Chemistry 54]

[0201]

[0202] [Chemistry 56]

[0203] [Chemistry 57]

[0204] [Chem.58]

[0205] [Chemistry 59]

[0206] [Transformation 60]

[0207] [Chemistry 61]

[0208] [Chemistry 62]

[0209]

[0210] Among these (P1-1-1-1-1) to (P7-12-1), the preferred points for the optical properties of the polymer of the present invention are (P1-2-1-1-1) to (P1-2-5-1-4), (P2-2-1) to (P2-2-3), (P3-2-1) to (P3-2-2), (P4-1-1) to (P4-2-9), and (P5-1-1) to (P5-1-19).

[0211] In the polymer of the present invention, the content of photoreactive reverse wavelength dispersive unit A in the polymer is 1 mol% to 50 mol%, preferably 5 mol% to 45 mol%, and more preferably 20 mol% to 45 mol.

[0212] In the polymer of the present invention, when it contains repeating units represented by (2A), (2B), (2C) and (2D), the content of repeating units represented by (2A), (2B), (2C) and (2D) in the polymer is 1 mol% to 99 mol%, preferably 10 mol% to 70 mol%, and more preferably 15 mol% to 60 mol.

[0213] The weight-average molecular weight of the polymer of the present invention is preferably 1,000 or more and 100,000 or less, and particularly preferably 1,100 or more and 50,000 or less.

[0214] In the case of the polymer of the present invention, with a short wavelength shift in the absorption band and configured as a film, a film with low yellowness (YI) can be provided, preferably with at least one end being a monocarboxylic acid ester.

[0215] As a monocarboxylic acid ester, the following chemical formula (2') shows the structure.

[0216]

[0217] [In this context, in the aforementioned chemical formula (2'), R10 represents a group consisting of alkyl groups with 1 to 20 carbon atoms that can be substituted, cycloalkyl groups with 3 to 8 carbon atoms that can be substituted, and aromatic groups with 3 to 12 carbon atoms that can be substituted.]

[0218] **Indicates the bonding position with other structures in the aforementioned main-chain polymer.

[0219] In formula (2'), R10 can be an alkyl group with 1 to 20 carbon atoms, for example: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, eicosyl, of which methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, and tributyl are preferred, and methyl and ethyl are particularly preferred for ease of introduction.

[0220] Examples of cycloalkyl groups with 3 to 8 carbon atoms include cyclohexyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.

[0221] As aromatic groups with 3 to 12 carbon atoms, examples include phenyl, naphthyl, biphenyl, and pyridyl.

[0222] As a monocarboxylic acid ester, for example, the structures shown in the following chemical formulas (2'-1) to (2'-37) can be listed.

[0223] [Chemistry 65]

[0224] [**Indicates the bonding position with other structures in the aforementioned main-chain polymer.]

[0225] Among these (2'-1)~(2'-37), the points that are easier to import are preferably (2'-1)~(2'-13) and (2'-20)~(2'-37), and particularly preferably (2'-1)~(2'-6), (2'-13), (2'-20)~(2'-23), (2'-29), (2'-31)~(2'-36), etc.

[0226] The polymers of the present invention having at least one end as a monocarboxylic acid ester can be exemplified by structures shown in the following chemical formulas (PA1-1-1-1-1) to (PA7-12-1).

[0227]

[0228] [Chemistry 67]

[0229] [Chemistry 68]

[0230] [Chemistry 69]

[0231] [Chemistry 70]

[0232] [Chemistry 71]

[0233] [Chemistry 72]

[0234] [Chemistry 73]

[0235] [Chemistry 74]

[0236] [Chemistry 75]

[0237] [Chemistry 76]

[0238] [Chemistry 77]

[0239] [Chemistry 78]

[0240] [Chemistry 79]

[0241] [Chemistry 80]

[0242] [Chemistry 81]

[0243]

[0244] [Chemistry 83]

[0245] [Chemistry 84]

[0246] [Chemistry 85]

[0247] [Chemistry 86]

[0248] [Chemistry 87]

[0249] [Chemistry 88]

[0250]

[0251] (In the aforementioned chemical formulas (PA1-1-1-1-1) to (PA7-12-1), R10 is synonymous with R10 in the aforementioned chemical formula (2').

[0252] Among these chemical formulas (PA1-1-1-1-1) to (PA7-12-1), those with good optical properties are preferably (PA1-2-1-1-1) to (PA1-2-5-1-4), (PA2-2-1) to (PA2-2-3), (PA3-2-1) to (PA3-2-2), (PA4-1-1) to (PA5-1-19), and (PA7-1-1) to (PA7-12-1).

[0253] The method for manufacturing the polymer of the present invention can be carried out by polymerizing a raw material composition comprising a dihydroxy compound represented by the following chemical formula (1'), and it is particularly preferred that the raw material composition comprises one or more compounds selected from the group consisting of dicarboxylic acids, dichlorocarboxylic acids, and dicarboxylic acids. The method for manufacturing the polymer of the present invention is also included in one embodiment of the present invention.

[0254]

[0255] [In the aforementioned chemical formula (1'), R0, R1, R2, R3, and R4 independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1). Ar represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are designated as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, or condensed aromatic rings may have substituents.]

[0256]

[0257] In the aforementioned chemical formula (Z1), Rz3 and Rz4 independently represent hydrogen atoms, halogen atoms, or alkyl groups with 1 to 8 carbon atoms, respectively.

[0258] Arz represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are considered as the atoms constituting the ring. These monocyclic, polycyclic, or condensed aromatic rings may have substituents. The wavy part indicates the bond position with the portion of formula (1) other than R0, R1, R2, R3, or R4.

[0259] In formula (1'), R0, R1, R2, R3, and R4 independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, or a group represented by formula (Z1); as a halogen atom, examples include chlorine atom, bromine atom, iodine atom, and fluorine atom; as an alkyl group having 1 to 8 carbon atoms, examples include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, and octyl.

[0260] In formula (Z1), Rz3 and Rz4 independently represent hydrogen atoms, halogen atoms, or alkyl groups having 1 to 8 carbon atoms, respectively; as halogen atoms, examples include chlorine atoms, bromine atoms, iodine atoms, and fluorine atoms; as alkyl groups having 1 to 8 carbon atoms, examples include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, and octyl.

[0261] In formula (Z1), Rz3 and Rz4 are points that represent the good optical properties of the polymer of the present invention. These points are preferably hydrogen atoms, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, second butyl, and third butyl, with hydrogen atoms, methyl, and ethyl being particularly preferred.

[0262] Arz represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are defined as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings may have substituents.

[0263] Arz refers to the group of atoms consisting of carbon, nitrogen, oxygen and sulfur atoms as the atoms constituting the ring. It can be a monocyclic aromatic ring with substituents, for example, benzene, pyridine, pyrazine, pyrimidine, pyridazine, furan, pyrrole, imidazole, thiophene, pyrazole, oxazole, isoxazole, thiazole and triazole.

[0264] In Arz, atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are designated as the atoms constituting the ring. These atoms can be polycyclic aromatic rings with substituents, such as biphenyl, terphenyl, bipyridine, bithiophene, and bifuran.

[0265] Arz defines the atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms as the atoms constituting the ring. It can be a condensed aromatic ring with substituents. Examples include naphthalene, anthracene, phenanthrene, quinoline, benzofuran, benzimidazole, benzothiophene, indole, indazole, benzoxazole, benzothiazole, and benzotriazole.

[0266] As an Arz, from an easily accessible point of view, it is preferable to select atoms from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms as the atoms constituting the ring, and to have a monocyclic aromatic ring that can have substituents. For the polymer of the present invention to exhibit good optical properties, this aromatic ring is further preferably a benzene ring, furan ring, thiophene ring, thiazole ring, or oxazole ring; and for the polymer of the present invention to further exhibit good optical properties, a benzene ring or thiophene ring is even more preferred.

[0267] R0, R1, R2, R3, and R4 are preferably groups represented by hydrogen atom, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, terbutyl, or the following chemical formulas (Z1-1) to (Z1-4) for the purpose of producing excellent optical properties after incorporation into the polymer of the present invention. For ease of incorporation, hydrogen atom, methyl, and ethyl are particularly preferred.

[0268]

[0269] In chemical formula (1'), Ar can be listed as the same Ar as in chemical formula (1). As a preferred example, the structures shown in the following chemical formulas (Ar-1) to (Ar-7) can be listed.

[0270] [Chemistry 93]

[0271] In the aforementioned chemical formulas (Ar-1) to (Ar-7), X1, X2, X3, X4, X5, X6, X7, and X8 independently represent hydrogen atoms or alkyl groups with 1 to 8 carbon atoms, alkoxy groups with 1 to 6 carbon atoms, halogen atoms, nitro groups, cyano groups, alkylthio groups with 1 to 6 carbon atoms, or dialkylamine groups with 2 to 8 carbon atoms.

[0272] Re represents an alkyl group with 1 to 10 hydrogen atoms or carbon atoms.

[0273] **Indicates the bond positions with the parts of the aforementioned chemical formula (1) other than Ar.

[0274] In (Ar-1) to (Ar-7), X1, X2, X3, X4, X5, X6, X7, and X8 independently represent a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a halogen atom, a nitro group, a cyano group, an alkylthio group with 1 to 6 carbon atoms, or a dialkylamino group with 2 to 8 carbon atoms; examples of alkyl groups with 1 to 8 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, and octyl; examples of alkoxy groups with 1 to 6 carbon atoms include... Examples of halogen atoms include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, dibutoxy, tributoxy, pentoxy, and hexoxy; halogen atoms include, for example, fluorine, chlorine, bromine, and iodine; alkylthio groups with 1 to 6 carbon atoms include, for example, methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, dibutylthio, tributylthio, pentoxy, and hexylthio; and dialkylamino groups with 2 to 8 carbon atoms include, for example, dimethylamino, diethylamino, dipropylamino, and dibutylamino.

[0275] X1, X2, X3, X4, X5, X6, X7, and X8 are preferably hydrogen atoms, alkyl groups with 1 to 8 carbon atoms, alkoxy groups with 1 to 6 carbon atoms, or halogen atoms, which have excellent optical properties after being incorporated into the polymer of the present invention. They are particularly preferably hydrogen atoms, methyl groups, methoxy groups, or halogen atoms, which are easy to incorporate.

[0276] As the dihydroxy compound represented by the aforementioned chemical formula (1'), the dihydroxy compound represented by the following chemical formulas (1'-1-1) to (1'-7-4) is preferred.

[0277]

[0278] [Chem. 95]

[0279]

[0280]

[0281]

[0282]

[0283] [Chemistry 100]

[0284] Among these (1'-1-1)~(1'-7-4), the preferred ones are (1'-2-1)~(1'-2-11), (1'-6-1)~(1'-6-4), and (1'-7-1)~(1'-7-4), and the most preferred ones are (1'-2-1)~(1'-2-6), (1'-2-1)~(1'-2-11), (1'-6-2)~(1'-6-3), and (1'-7-2).

[0285] Examples of dicarboxylic acids include, for instance, aliphatic polycarboxylic acids (specifically, saturated polycarboxylic acids with 2 to 20 carbon atoms such as oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, and sebacic acid, and unsaturated polycarboxylic acids such as maleic acid, fumaric acid, and itaconic acid), alicyclic polycarboxylic acids (cyclobutanedicarboxylic acid, trans-1,4-cyclohexanedicarboxylic acid, and cis-1,4-cyclohexanedicarboxylic acid), and aromatic polycarboxylic acids (terephthalic acid, isophthalic acid, phthalic acid, 4,4'-biphenyldicarboxylic acid, 4,4'-oxobis(benzoic acid), and 2,5-furandicarboxylic acid).

[0286] Examples of dichloro dicarboxylic acids include, for instance, saturated carboxylic acid dichloro with 2 to 20 carbon atoms such as oxalate dichloro, malonate dichloro, succinate dichloro, glutarate dichloro, adipic acid dichloro, and sebacic acid dichloro; unsaturated polycarboxylic acid dichloro such as fumarate dichloro and itaconic acid dichloro; alicyclic carboxylic acid dichloro such as cyclobutane dicarboxylic acid dichloro, cyclopentane dicarboxylic acid dichloro, trans-1,4-cyclohexane dicarboxylic acid dichloro, and cis-1,4-cyclohexane dicarboxylic acid dichloro; aromatic polycarboxylic acid dichloro such as terephthalic acid dichloro, isophthalic acid dichloro, phthalic acid dichloro, 4,4'-biphenyl dicarboxylic acid dichloro, 4,4'-oxobis(benzoic acid chloride), and 2,5-furan dicarboxylic acid dichloro.

[0287] In the method for manufacturing the polymer of the present invention, it is preferable to polymerize the raw material composition by further containing compounds represented by the following chemical formulas (2”A), (2”B), (2”C) and (2”D).

[0288]

[0289] In the aforementioned chemical formula (2”A), ring C, ring D and ring E independently represent rings selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings and aliphatic hydrocarbon rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms and sulfur atoms are set as the atoms constituting the rings. These monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings and aliphatic hydrocarbon rings may have substituents.

[0290] R5 and R6 may be the same or different, representing a group selected from the group consisting of hydrogen atoms, alkyl groups with 1 to 20 substituted carbon atoms, cycloalkyl groups with 3 to 8 substituted carbon atoms, and aromatic groups with 3 to 12 substituted carbon atoms.

[0291] Qn1 and Qn2 can be the same or different, representing hydroxyl, amino, carboxyl or -C(=O)Cl.

[0292] n is either 0 or 1.

[0293] In formula (2”A), ring C, ring D and ring E independently represent rings selected from groups consisting of monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings and aliphatic hydrocarbon rings. Atoms selected from groups consisting of carbon atoms, nitrogen atoms, oxygen atoms and sulfur atoms are set as the atoms constituting the rings. These monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings and aliphatic hydrocarbon rings may have substituents.

[0294] In a specific ring C, atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are designated as the atoms constituting the ring. It can be a monocyclic aromatic ring with substituents, for example, benzene, pyridine, pyrazine, pyrimidine, pyridazine, furan, pyrrole, imidazole, thiophene, pyrazole, oxazole, isoxazole, thiazole, and triazole.

[0295] The atoms in ring C are selected from the group consisting of carbon, nitrogen, oxygen and sulfur atoms, and can be polycyclic aromatic rings with substituents. Examples include biphenyl, terphenyl, bipyridine, bithiophene and bifuran.

[0296] A ring C can be a condensed aromatic ring, consisting of atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms, and can have substituents. Examples include naphthalene, anthracene, phenanthrene, quinoline, benzofuran, benzimidazole, benzothiophene, indole, indazole, benzoxazole, benzothiazole, and benzotriazole.

[0297] As a specific example of an aliphatic hydrocarbon ring that can have substituents, the group of atoms selected from carbon, nitrogen, oxygen and sulfur atoms in the ring C is used as the atoms constituting the ring. Examples include cyclopentane, cyclohexane and tricyclo[5.2.1.0(2,6)]decane.

[0298] For the ring C, it is preferable to use a monocyclic aromatic ring in which the atoms selected from the group consisting of carbon, nitrogen, oxygen and sulfur atoms are set as the atoms constituting the ring, and for ease of introduction, benzene ring is particularly preferred.

[0299] In formula (2”A), ring D and ring E independently represent rings selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings and aliphatic hydrocarbon rings, respectively. These rings have atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms and sulfur atoms as the atoms constituting the rings. These monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings and aliphatic hydrocarbons may have substituents.

[0300] For specific rings D and E, those similar to ring C can be listed independently for ease of introduction. It is preferable to use a monocyclic aromatic ring in which the atoms selected from the group consisting of carbon, nitrogen, oxygen and sulfur atoms are set as the atoms constituting the ring. For ease of introduction, benzene ring is particularly preferred.

[0301] Here, as substituents in monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings, examples include alkyl groups with 1 to 8 carbon atoms, halogen atoms, alkoxy groups with 1 to 4 carbon atoms, and acetyl groups with 2 to 4 carbon atoms; as alkyl groups with 1 to 8 carbon atoms, examples include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, and octyl; as halogen atoms, examples include fluorine, chlorine, bromine, and iodine; as alkoxy groups with 1 to 4 carbon atoms, examples include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, dibutoxy, and tributoxy; as acetyl groups with 2 to 4 carbon atoms, examples include acetyl, propoxy, and butyl.

[0302] In formula (2”A), R5 and R6 may be the same or different, representing a group selected from the group consisting of hydrogen atoms, alkyl groups with 1 to 20 substituted carbon atoms, cycloalkyl groups with 3 to 8 substituted carbon atoms, and aromatic groups with 3 to 12 substituted carbon atoms.

[0303] Examples of alkyl groups having 1 to 20 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, and eicosyl. Among these, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, and tributyl are preferred for their superior optical properties after incorporation into the polymer of the present invention, and methyl and ethyl are particularly preferred for their ease of incorporation.

[0304] Examples of cycloalkyl groups with 3 to 8 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.

[0305] As aromatic groups with 3 to 12 carbon atoms, examples include phenyl, naphthyl, biphenyl, and pyridyl.

[0306] In formula (2”A), Qn1 and Qn2 can be the same or different, representing hydroxyl, amino, carboxyl or -C(=O)Cl.

[0307]

[0308] [In the aforementioned chemical formula (2”B), Qn3 and Qn4 may be the same or different, representing hydroxyl, amino, carboxyl or -C(=O)Cl.]

[0309]

[0310] In the aforementioned chemical formula (2”C), X9 represents an alkyl chain with 1 to 10 carbon atoms and a single bond.

[0311] X10 represents -O- or -N(Rc)-.

[0312] X11 represents -O- or -N(Rd)-.

[0313] Rc and Rd can be the same or different, representing alkyl groups with 1 to 10 hydrogen atoms or carbon atoms.

[0314] Qn5 and Qn6 can be the same or different, representing hydroxyl, amino, carboxyl, or -C(=O)Cl.

[0315]

[0316] In the aforementioned chemical formula (2”D), ring G represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, spirocyclic rings, and aliphatic hydrocarbon rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are designated as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, spirocyclic rings, and aliphatic hydrocarbon rings may have substituents.

[0317] L13 and L14 can be the same or different, representing single bonds and alkyl chains with 1 to 6 carbon atoms.

[0318] Qn7 and Qn8 can be the same or different, representing hydroxyl, amino, carboxyl, or -C(=O)Cl.

[0319] In formula (2”D), ring G independently represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, spirocyclic rings and aliphatic hydrocarbon rings. Atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms and sulfur atoms are set as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, spirocyclic rings and aliphatic hydrocarbon rings may have substituents.

[0320] Specific examples of a monocyclic aromatic ring that can have substituents, in which atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are designated as the atoms constituting the ring, include benzene, pyridine, pyrazine, pyrimidine, pyridazine, furan, pyrrole, imidazole, thiophene, pyrazole, oxazole, isoxazole, thiazole, and triazole.

[0321] In ring G, atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are designated as the atoms constituting the ring. It can be a polycyclic aromatic ring with substituents, for example, biphenyl, terphenyl, bipyridine, bithiophene, and bifuran.

[0322] In ring G, atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are designated as the atoms constituting the ring. It can be a condensed aromatic ring with substituents. Examples include naphthalene, anthracene, phenanthrene, quinoline, benzofuran, benzimidazole, benzothiophene, indole, indazole, benzoxazole, benzothiazole, and benzotriazole.

[0323] As a spirocycle in ring G, in which atoms selected from the group consisting of carbon, nitrogen, oxygen and sulfur atoms are designated as the atoms constituting the ring, and which may have substituents, the structure shown in the following chemical formula (sp1-1) can be listed.

[0324]

[0325] As a ring G, atoms selected from the group consisting of carbon, nitrogen, oxygen and sulfur atoms are set as the atoms constituting the ring. It can be an aliphatic hydrocarbon ring with substituents, for example, cyclopentane, cyclohexane, tricyclo[5.2.1.0(2,6)]decane.

[0326] For ring G, it is preferable to select a group of atoms consisting of carbon, nitrogen, oxygen and sulfur atoms as the atoms constituting the ring, preferably a monocyclic aromatic ring or an aliphatic hydrocarbon ring, with the advantage of good optical properties of the polymer, especially benzene, cyclohexane and tricyclic [5.2.1.0(2,6)]decane.

[0327] As specific examples of compounds represented by formula (2”A), structures represented by the following chemical formulas (2”A-1-1) to (2”A-2-20) can be listed.

[0328] [Chemistry 106]

[0329] [Chemistry 107]

[0330] [Chemistry 108]

[0331] [Chemistry 109]

[0332] [Chemical 110]

[0333] [Chemistry 111]

[0334] [In formulas (2”A-1-1)~(2”A-2-20), Qn1 and Qn2 may be the same or different, representing hydroxyl, amino, carboxyl, or -C(=O)Cl.]

[0335] Among these (2”A-1-1) to (2”A-2-20), the polymers of the present invention that are easy to synthesize are preferably (2”A-1-1) to (2”A-1-10), (2”A-1-36) to (2”A-1-40), (2”A-1-51) to (2”A-1-55), and (2”A-2-1) to (2”A-2-4), and the polymers of the present invention that have excellent optical properties are particularly preferred (2”A-1-1) to (2”A-1-10), (2”A-1-36) to (2”A-1-40), and (2”A-1-51) to (2”A-1-55).

[0336] As specific examples of compounds represented by formula (2”B), structures represented by the following chemical formulas (2”B-1) to (2”B-2) can be listed.

[0337]

[0338] Of these (2”B-1) to (2”B-2), (2”B-1) is preferred due to its superior optical properties of the polymer of the present invention.

[0339] As specific examples of compounds represented by formula (2”C), structures represented by the following chemical formulas (2”C-1-1) to (2”C-2-23) can be listed.

[0340]

[0341] [Chemistry 114]

[0342] [Chemistry 115]

[0343] Among these (2”C-1-1) to (2”C-2-23), those with superior optical properties of the polymer of the present invention are (2”C-1-4) to (2”C-1-8) and (2”C-2-1) to (2”C-2-23).

[0344] As specific examples of compounds represented by formula (2”D), structures represented by the following chemical formulas (2”D-1-1) to (2”D-14-1) can be listed.

[0345] [Chemistry 116]

[0346] [Chemistry 117]

[0347] [Chemistry 118]

[0348]

[0349] Among these (2”D-1-1) to (2”D-14-1), the polymers of the present invention with superior optical properties are (2”D-1-1), (2”D-2-1), (2”D-3-1), (2”D-3-1), (2”D-4-3), (2”D-7-3), (2”D-7-4), (2”D-7-4) to (2”D-13-1), and (2”D-14-1).

[0350] The method for manufacturing the polymer of the present invention aims to adjust the physical properties of the generated polymer, and polyhydroxy compounds can also be used as raw materials.

[0351] Examples of polyhydroxy compounds include, for example, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, 1,3-propanediol, 1,2-propanediol, 1,4-butanediol, 2,2-butanediol, 2,3-butanediol, 2,4-dimethyl-2,4-pentanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 2-methyl-1,3-propanediol, 3-methyl-1,5-heptanediol, cyclopentanediol, cyclohexanediol, 1,8-propanediol, etc. -Octanediol, 1,9-Nonanediol, 1,10-Decanediol, 1,12-Dodecanediol, Hydroquinone, Tetramethylhydroquinone, 4,4'-Dihydroxybiphenyl, Vanillyl alcohol, Furandimethyl alcohol, 2,2-bis(4-hydroxyphenyl)propane, 4,4'-(1,3-dimethylbutylene)diol, 6,6'-Dihydroxy-4,4,4',4',7,7'-Hexamethyl-2,2'-spirobicroma ne), tricyclodecanediethanol, 2,2'-dihydroxydiphenyl ether, 4,4'-methylenebis(2,6-dimethylphenol), 3,3',5,5'-tetramethylbiphenyl-4,4'-diol, 1,1-bis(4-hydroxyphenyl)cyclohexane, 2-buten-1,4-diol, 2,2-diisobutyl-1,3-propanediol, bis[4-(2-hydroxyethoxy)phenyl] benzoxate, 2,2,4,4-tetramethyl-1,3-cyclobutanediol, 1 ,4-bis(3-hydroxyphenoxy)benzene, 4,4'-biscyclohexanol, bis(4-hydroxy-3-methylphenyl)sulfide, 2,2-diisopentyl-1,3-propanediol, 4,4'-dihydroxydiphenylmethane, dihydroxynaphthalene, 2,2-bis(3-cyclohexyl-4-hydroxyphenyl)propane, bis(4-hydroxyphenyl)sulfonium, 1,4-benzenedimethanol, 3,9-bis(1,1-dimethyl-2-hydroxyethyl)-2,4,8,10-tetraoxospirol[5].5] Undecane, 4,4'-biphenyldimethylethanol, 1,3-bis(hexafluoro-α-hydroxyisopropyl)benzene, 3,6-dihydroxybenzobornene, 2-benzyloxy-1,3-propanediol, 4,4'-dihydroxybenzophenone, 4,4'-dihydroxydiphenyl ether, 9,9-bis(4-hydroxyphenyl)fluorene, 1,8-bis(hydroxymethyl)anthracene, 1,4-bis[2-(4-hydroxyphenyl)-2-propyl]benzene, α, α'-bis(4-hydroxy-3,5-dimethylphenyl)-1,4-diisopropylbenzene, 2,2-bis(4-hydroxy-3,5-dimethylphenyl)propane, 2,2'-methylenebis(4-methylphenol), 1,3-bis(4-hydroxyphenoxy)benzene, 2,2-bis(4-hydroxyphenyl)butane, 1,1-bis(4-hydroxy-3-methylphenyl)cyclohexane, 2,2-bis(4-hydroxy-3-methylphenyl) Propane, 2,2'-dihydroxybenzophenone, 2,2'-bis(hydroxymethyl)diphenyl ether, 7,7'-dihydroxy-4,4,4',4'-tetramethyl-2,2'-spirobenzyl dihydropyran, 1,4-bis(hydroxymethyl)-2,3,5,6-tetramethylbenzene, 4,4'-ethylidene bisphenol, cyclohexanediol, polyethylene glycol, 1,3-adamantanediol, 1-hydroxy-3-(hydroxymethyl)adamantane, 2,7-Dihydroxy-9H-fluorene-9-one, divalent hydroxyl compounds of polyethylene glycol of various molecular weights, glycerol, trimethylolpropane, triethanolamine, 2,3,4,4'-tetrahydroxybenzophenone, 1,2,3-butanetriol, trivalent hydroxyl compounds of 2,6-bis(hydroxymethyl)-4-methylphenol, and tetravalent hydroxyl compounds of neopentyl tetrol, along with various sugars, can be listed as other polyhydroxyl compounds.

[0352] The aggregation method is not particularly limited, but refers to the aggregation methods known in this field. For example, interface aggregation can be listed.

[0353] As an example of interfacial polymerization, the interfacial polymerization of a water-organic solvent bilayer system can be cited.

[0354] During the interfacial polymerization of water-organic solvent binary systems, phase transfer catalysts and bases are preferred for promoting the reaction.

[0355] Examples of phase transfer catalysts include, for example, ammonium salts of benzyltriethylammonium chloride, benzyltriethylammonium bromide, tetrabutylammonium chloride, tetrabutylammonium bromide, tetrapentylammonium chloride, tetrapentylammonium bromide, tetraheptylammonium chloride, tetraheptylammonium bromide, dimethyldipalmitylammonium chloride, and dimethyldipalmitylammonium bromide; and phosphonium salts of tetraethylphosphonium chloride, tetraethylphosphonium bromide, tributylhexylphosphonium chloride, tributylhexylphosphonium bromide, tetra-n-octylphosphonium chloride, tetra-n-octylphosphonium bromide, tributyl-n-octylphosphonium chloride, tributyl-n-octylphosphonium bromide, tetrabutylphosphonium chloride, tetrabutylphosphonium bromide, tetraphenylphosphonium bromide, and tetraphenylphosphonium chloride.

[0356] Examples of bases include alkali metal hydroxides of sodium hydroxide and potassium hydroxide; alkali metal carbonates of sodium carbonate and potassium carbonate; alkali metal hydrides of sodium hydride; alkali metal alkoxides of sodium methoxide and sodium ethoxide; and tetrabutylammonium hydroxide.

[0357] The preferred reaction temperature for interfacial polymerization is above -30°C and below 50°C, and the most preferred temperature is above 0°C and below 40°C. The preferred reaction time is above 30 minutes and below 24 hours.

[0358] As organic solvents used in interfacial polymerization, any organic solvent that is harmless to the reaction can be used. Examples include ether solvents such as dioxane, tetrahydrofuran (hereinafter referred to as THF), diethyl ether, diisopropyl ether, cyclopentylmethyl ether, and dimethoxyethane; aromatic solvents such as benzene, toluene, xylene, chlorobenzene, dichlorobenzene, and pyridine; halogen solvents such as dichloromethane, chloroform, and carbon tetrachloride; and amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone. These solvents can be used alone or in any mixture of two or more.

[0359] As a solution polymerization method, methods that use condensing agents in organic solvents can be cited as examples.

[0360] As organic solvents used in solution polymerization, any organic solvent that is harmless to the reaction can be used. Examples include ether solvents such as dioxane, THF, diethyl ether, diisopropyl ether, cyclopentylmethyl ether, and dimethoxyethane; aromatic solvents such as benzene, toluene, xylene, chlorobenzene, dichlorobenzene, and pyridine; halogen solvents such as dichloromethane, chloroform, and carbon tetrachloride; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and NMP; and ester solvents such as ethyl acetate and butyl acetate. These solvents can be used alone or in any mixture of two or more in any ratio.

[0361] Examples of condensing agents used in solution polymerization include, for instance, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride, N,N'-diisopropylcarbodiimide, N,N'-dicyclohexylcarbodiimide, bis(2,6-diisopropylphenyl)carbodiimide, bis(trimethylsilyl)carbodiimide, and 1-cyclohexyl-3-(2-morpholinylethyl)carbodiimide. Among the following, 1-[3-(dimethylamino)propyl]-3-methyliodoethylcarbodiimide, p-toluenesulfonate, N,N'-di-tert-butylcarbodiimide, and 1-[3-(dimethylamino)propyl]-3-methyliodoethylcarbodiimide are preferred: 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride, N,N'-diisopropylcarbodiimide, and N,N'-dicyclohexylcarbodiimide. Two or more of these ester-forming condensing agents may be used.

[0362] The preferred reaction temperature for solution polymerization is above -30℃ and below 90℃, and the most preferred temperature is above 0℃ and below 60℃. The preferred reaction time is above 30 minutes and below 24 hours.

[0363] In solution polymerization, it is preferable to add an alkali to ensure the smooth progress of the reaction.

[0364] Examples of bases used include, for example, organic bases, inorganic bases, organometallic compounds, metal alkoxides, and metal amides.

[0365] Examples of organic bases include triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, piperidine, piperazine, pyrrolidine, morpholine, N-methylmorpholine, imidazole, and N-methylimidazolium.

[0366] Examples of inorganic bases include lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, potassium bicarbonate, sodium hydride, and potassium hydride.

[0367] Examples of organometallic compounds include n-butyllithium, dibutyllithium, tert-butyllithium, and phenyllithium.

[0368] Examples of metal alkoxides include sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide.

[0369] Examples of metallic amides include lithium amide, sodium amide, lithium amide diisopropylidene, lithium hexamethyldisilane azido, sodium hexamethyldisilane azido, and potassium hexamethyldisilane azido.

[0370] Among bases, organic bases are preferred for their better reaction performance and lower cost, with triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, piperidine, piperazine, and pyrrolidine being even better.

[0371] There are no particular restrictions on the amount of alkali used, and the amount of solvent that can be used is also not limited.

[0372] Alkalis can be used in liquid, granular, particulate, or powdered solid forms, depending on their properties. Furthermore, these solutions can also be used without particular limitation on their concentration.

[0373] Another aspect of the present invention is a dihydroxy compound represented by the following formula (1') (hereinafter, sometimes also referred to as the dihydroxy compound of the present invention). The dihydroxy compound of the present invention serves as a raw material for the polymer of the present invention.

[0374]

[0375] [In the aforementioned chemical formula (1'), R0, R1, R2, R3, and R4 independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1). Ar represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are designated as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, or condensed aromatic rings may have substituents.]

[0376]

[0377] In formula (Z1), Rz3 and Rz4 independently represent hydrogen atoms, halogen atoms, or alkyl groups with 1 to 8 carbon atoms, respectively.

[0378] Arz represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are considered as the atoms constituting the ring. These monocyclic, polycyclic, or condensed aromatic rings may have substituents. The wavy part indicates the bond position with the portion of formula (1) other than R0, R1, R2, R3, or R4.

[0379] In formula (1'), R0, R1, R2, R3, and R4 independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, or a group represented by chemical formula (Z1); as a halogen atom, chlorine atom, bromine atom, iodine atom, and fluorine atom can be listed; as an alkyl group having 1 to 8 carbon atoms, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, and octyl can be listed.

[0380] In formula (Z1), Rz3 and Rz4 independently represent hydrogen atoms, halogen atoms, or alkyl groups having 1 to 8 carbon atoms, respectively; examples of halogen atoms include chlorine atoms, bromine atoms, iodine atoms, and fluorine atoms; examples of alkyl groups having 1 to 8 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, and octyl.

[0381] In formula (Z1), Rz3 and Rz4 are points that represent the good optical properties of the polymer of the present invention. These points are preferably hydrogen atoms, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, second butyl, and third butyl, with hydrogen atoms, methyl, and ethyl being particularly preferred.

[0382] Arz represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are defined as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings may have substituents.

[0383] Arz refers to the group of atoms consisting of carbon, nitrogen, oxygen and sulfur atoms as the atoms constituting the ring. It can be a monocyclic aromatic ring with substituents, for example, benzene, pyridine, pyrazine, pyrimidine, pyridazine, furan, pyrrole, imidazole, thiophene, pyrazole, oxazole, isoxazole, thiazole and triazole.

[0384] In Arz, atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are designated as the atoms constituting the ring. These atoms can be polycyclic aromatic rings with substituents, such as biphenyl, terphenyl, bipyridine, bithiophene, and bifuran.

[0385] Arz defines the atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms as the atoms constituting the ring. It can be a condensed aromatic ring with substituents. Examples include naphthalene, anthracene, phenanthrene, quinoline, benzofuran, benzimidazole, benzothiophene, indole, indazole, benzoxazole, benzothiazole, and benzotriazole.

[0386] As an Arz, from an easily accessible point of view, it is preferable to use atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms as the atoms constituting the ring, and to form a monocyclic aromatic ring that can have substituents. For the polymer of the present invention to exhibit good optical properties, the aromatic ring is further preferably a benzene ring, furan ring, thiophene ring, thiazole ring, or oxazole ring; and for the polymer of the present invention to further exhibit good optical properties, a benzene ring or thiophene ring is even more preferred.

[0387] R0, R1, R2, R3, and R4 are preferably groups represented by hydrogen atom, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, terbutyl, or the following chemical formulas (Z1-1) to (Z1-4) for the purpose of producing excellent optical properties after incorporation into the polymer of the present invention. For ease of incorporation, hydrogen atom, methyl, and ethyl are particularly preferred.

[0388] [Chemistry 122]

[0389] In formula (1'), Ar represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings and condensed aromatic rings, wherein the atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms and sulfur atoms are set as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings and condensed aromatic rings may have substituents.

[0390] Here, examples of substituents in monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings include alkyl groups with 1 to 8 carbon atoms, halogen atoms, alkoxy groups with 1 to 4 carbon atoms, and acetyl groups with 2 to 4 carbon atoms.

[0391] Examples of alkyl groups having 1 to 8 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, and octyl.

[0392] Examples of halogen atoms include, for example, fluorine, chlorine, bromine, and iodine.

[0393] Examples of alkoxy groups with 1 to 4 carbon atoms include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, dibutoxy, and terbutoxy.

[0394] Examples of acetylated groups with 2 to 4 carbon atoms include acetylated, propionic, and butylated.

[0395] Ar can be a monocyclic aromatic ring consisting of atoms selected from the group consisting of carbon, nitrogen, oxygen and sulfur atoms, and can have substituents. Examples include benzene, pyridine, pyrazine, pyrimidine, pyridazine, furan, pyrrole, imidazole, thiophene, pyrazole, oxazole, isoxazole, thiazole and triazole.

[0396] In Ar, atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are designated as the atoms constituting the ring. Polycyclic aromatic rings with substituents can be used, such as biphenyl, terphenyl, bipyridine, bithiophene, and bifuran.

[0397] In Ar, atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are designated as the atoms constituting the ring. They can have substituents and condensed aromatic rings. Examples include naphthalene, anthracene, phenanthrene, quinoline, benzofuran, benzimidazole, benzothiophene, indole, indazole, benzoxazole, benzothiazole, and benzotriazole.

[0398] As for Ar, from an easily accessible point of view, it is preferable to use atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms as the atoms constituting the ring, and to have a monocyclic aromatic ring with substituents. To demonstrate the good optical properties of the polymer of the present invention, it is further preferable that the aromatic ring is a benzene ring, furan ring, thiophene ring, thiazole ring, or oxazole ring. To further demonstrate the good optical properties of the polymer of the present invention, benzene rings and thiophene rings are even more preferable.

[0399] As a better example of Ar, the structures shown by the following chemical formulas (Ar-1) to (Ar-7) can be listed.

[0400]

[0401] In the aforementioned chemical formulas (Ar-1) to (Ar-7), X1, X2, X3, X4, X5, X6, X7, and X8 independently represent a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a halogen atom, a nitro group, a cyano group, an alkylthio group with 1 to 6 carbon atoms, or a dialkylamine group with 2 to 8 carbon atoms.

[0402] Re represents an alkyl group with 1 to 10 hydrogen atoms or carbon atoms.

[0403] **Indicates the bond positions with the parts of the aforementioned chemical formula (1') other than Ar.

[0404] In formulas (Ar-1) to (Ar-7), X1, X2, X3, X4, X5, X6, X7, and X8 independently represent a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a halogen atom, a nitro group, a cyano group, an alkylthio group with 1 to 6 carbon atoms, or a dialkylamino group with 2 to 8 carbon atoms; examples of alkyl groups with 1 to 8 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, and octyl; examples of alkoxy groups with 1 to 6 carbon atoms include... Examples of halogen atoms include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, dibutoxy, tributoxy, pentoxy, and hexoxy; halogen atoms include, for example, fluorine, chlorine, bromine, and iodine; alkylthio groups with 1 to 6 carbon atoms include, for example, methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, dibutylthio, tributylthio, pentoxy, and hexylthio; and dialkylamino groups with 2 to 8 carbon atoms include, for example, dimethylamino, diethylamino, dipropylamino, and dibutylamino.

[0405] X1, X2, X3, X4, X5, X6, X7, and X8 are preferably, independently, hydrogen atoms, alkyl groups having 1 to 8 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, or halogen atoms, and are particularly preferably hydrogen atoms, methyl groups, methoxy groups, or halogen atoms.

[0406] As preferred examples of the dihydroxy compounds of the present invention, dihydroxy compounds represented by the following chemical formulas (1'-2) can be listed.

[0407]

[0408] In the aforementioned chemical formulas (1'-2), R0, R1, R2, R3, and R4 independently represent alkyl groups with 1 to 8 carbon atoms.

[0409] X6, X7, and X8 independently represent a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a halogen atom, a nitro group, a cyano group, an alkylthio group with 1 to 6 carbon atoms, or a dialkylamine group with 2 to 8 carbon atoms.

[0410] In formula (1'-2), R0, R1, R2, R3, and R4 independently represent hydrogen atoms or alkyl groups having 1 to 8 carbon atoms. Examples of alkyl groups having 1 to 8 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, and octyl.

[0411] For R0, R1, R2, R3, and R4, the most easily introduced sites are hydrogen atoms, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, and terbutyl, with hydrogen atoms, methyl, and ethyl being particularly preferred.

[0412] In formula (1'-2), X6, X7, and X8 independently represent a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a halogen atom, a nitro group, a cyano group, an alkylthio group with 1 to 6 carbon atoms, or a dialkylamino group with 2 to 8 carbon atoms; examples of alkyl groups with 1 to 8 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, and octyl; examples of alkoxy groups with 1 to 6 carbon atoms include methoxy, ethoxy The group can be alkyl, propoxy, isopropoxy, butoxy, isobutoxy, dibutoxy, tributoxy, pentoxy, or hexoxy; as a halogen atom, for example, fluorine, chlorine, bromine, or iodine; as an alkylthio group having 1 to 6 carbon atoms, for example, methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, dibutylthio, tributylthio, pentoxy, or hexylthio; as a dialkylamino group having 2 to 8 carbon atoms, for example, dimethylamino, diethylamino, dipropylamino, or dibutylamino.

[0413] As for X6, X7, and X8, the dihydroxy compounds of the present invention are preferably hydrogen atoms, alkyl groups having 1 to 8 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, or halogen atoms, and are particularly preferred for ease of incorporation, being hydrogen atoms, methyl groups, methoxy groups, chlorine atoms, bromine atoms, or fluorine atoms.

[0414] As a better example of a dihydroxy compound represented by the general formula (1'), the following dihydroxy compounds represented by chemical formulas (1'-2-1) to (1'-7-4) are listed.

[0415]

[0416] [Chemistry 126]

[0417]

[0418]

[0419]

[0420]

[0421] Among these (1'-2-1)~(1'-7-4), the preferred ones are (1'-2-2)~(1'-2-11), (1'-6-1)~(1'-6-4), and (1'-7-1)~(1'-7-4), and the most preferred ones are (1'-2-1)~(1'-2-6), (1'-2-1)~(1'-2-11), (1'-6-2)~(1'-6-3), and (1'-7-1).

[0422] The method for manufacturing the dihydroxy compound represented by formula (1') of the present invention is a method of reacting the dihydroxy compound represented by the following chemical formula (3) with the ketone represented by the following chemical formula (4').

[0423]

[0424] In the aforementioned chemical formula (3), R0, R1, and R7 independently represent hydrogen atoms, halogen atoms, or alkyl groups with 1 to 8 carbon atoms.

[0425] R2f represents a hydrogen atom, a halogen atom, an alkyl group with 1 to 8 carbon atoms, or a methyl group.

[0426] In the aforementioned chemical formula (4'), Ar represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are designated as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings may have substituents. R8 represents an alkyl group having 1 to 8 carbon atoms, or a haloalkyl group having 1 to 6 carbon atoms.

[0427] In the aforementioned chemical formula (1'), Ar represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are designated as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings may have substituents. R0, R1, R2, R3, and R4 independently represent hydrogen atoms, halogen atoms, alkyl groups having 1 to 8 carbon atoms, or groups represented by the following chemical formula (Z1).

[0428]

[0429] In the aforementioned formula (Z1), Rz3 and Rz4 independently represent hydrogen atoms, halogen atoms, or alkyl groups with 1 to 8 carbon atoms, respectively.

[0430] Arz represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are considered as the atoms constituting the ring. These monocyclic, polycyclic, or condensed aromatic rings may have substituents. The wavy part indicates the bond position with the portion of formula (1) other than R0, R1, R2, R3, or R4.

[0431] In formula (3), R0, R1, and R7 independently represent hydrogen atoms or alkyl groups with 1 to 8 carbon atoms. For example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, terbutyl, pentyl, hexyl, heptyl, and octyl are examples of alkyl groups with 1 to 8 carbon atoms.

[0432] R2f represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, or a methyl group. Examples of alkyl groups having 1 to 8 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, and octyl.

[0433] As for R0, R1, R2f, and R7, the dihydroxy compound of the present invention is preferably composed of hydrogen atom, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, or terbutyl, with the advantage of excellent optical properties after incorporation into the polymer of the present invention. For ease of incorporation, hydrogen atom, methyl, and ethyl are particularly preferred.

[0434] As a specific dihydroxy compound represented by formula (3), the structures shown in the following chemical formulas (3-1) to (3-11) can be exemplified.

[0435]

[0436]

[0437] Among these (3-1) to (3-11), (3-1) to (3-4) and (3-10) to (3-11) are preferred, and (3-1), (3-3), and (3-10) to (3-11) are particularly preferred.

[0438] The dihydroxy compound shown in formula (3) can be easily prepared according to known or documented methods. Alternatively, commercially available products can also be used.

[0439] In formula (4'), R8 represents an alkyl group having 1 to 8 carbon atoms or a haloalkyl group having 1 to 6 carbon atoms. Examples of alkyl groups having 1 to 8 carbon atoms include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl. Examples of haloalkyl groups having 1 to 6 carbon atoms include chloromethyl and 2,2,2-trifluoroethyl.

[0440] As R8, the dihydroxy compound of the present invention is preferably methyl, ethyl, propyl, or butyl, which has excellent optical properties after being incorporated into the polymer of the present invention, and is particularly preferred for ease of incorporation, with methyl and ethyl being the most readily incorporated.

[0441] In formula (4'), Ar represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings and condensed aromatic rings, wherein the atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms and sulfur atoms are set as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings and condensed aromatic rings may have substituents.

[0442] Here, examples of substituents in monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings include alkyl groups with 1 to 8 carbon atoms, halogen atoms, alkoxy groups with 1 to 4 carbon atoms, and acetyl groups with 2 to 4 carbon atoms.

[0443] Examples of alkyl groups having 1 to 8 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, and octyl.

[0444] Examples of halogen atoms include, for example, fluorine, chlorine, bromine, and iodine.

[0445] Examples of alkoxy groups with 1 to 4 carbon atoms include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, dibutoxy, and terbutoxy.

[0446] Examples of acetylated groups with 2 to 4 carbon atoms include acetylated, propionic, and butylated groups.

[0447] Ar can be a monocyclic aromatic ring consisting of atoms selected from the group consisting of carbon, nitrogen, oxygen and sulfur atoms, and can have substituents. Examples include benzene, pyridine, pyrazine, pyrimidine, pyridazine, furan, pyrrole, imidazole, thiophene, pyrazole, oxazole, isoxazole, thiazole and triazole.

[0448] In Ar, atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are designated as the atoms constituting the ring. Polycyclic aromatic rings with substituents can be used, such as biphenyl, terphenyl, bipyridine, bithiophene, and bifuran.

[0449] Ar can be a ring composed of atoms selected from the group consisting of carbon, nitrogen, oxygen and sulfur atoms. It can be a condensed aromatic ring with substituents. Examples include naphthalene, anthracene, phenanthrene, quinoline, benzofuran, benzimidazole, benzothiophene, indole, indazole, benzoxazole, benzothiazole and benzotriazole.

[0450] As for Ar, from an easy-to-access point, atoms selected from the group consisting of carbon, nitrogen, oxygen and sulfur atoms are preferred as the atoms constituting the ring, and a monocyclic aromatic ring with substituents is preferred. From the point of excellent optical properties after being introduced into the polymer of the present invention, the dihydroxy compound of the present invention is preferably a benzene ring, furan ring, thiophene ring, thiazole ring or oxazole ring, and a benzene ring or thiophene ring is further preferred.

[0451] As a better example of Ar, the structures shown by the following chemical formulas (Ar-1) to (Ar-7) can be listed.

[0452] [Chemistry 135]

[0453] In the aforementioned chemical formulas (Ar-1) to (Ar-7), X1, X2, X3, X4, X5, X6, X7, and X8 independently represent a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a halogen atom, a nitro group, a cyano group, an alkylthio group with 1 to 6 carbon atoms, or a dialkylamine group with 2 to 8 carbon atoms.

[0454] Re represents an alkyl group with 1 to 10 hydrogen atoms or carbon atoms.

[0455] **Indicates the bond positions with the parts of the aforementioned chemical formula (1) other than Ar.

[0456] In formulas (Ar-1) to (Ar-7), X1, X2, X3, X4, X5, X6, X7, and X8 independently represent a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a halogen atom, a nitro group, a cyano group, an alkylthio group with 1 to 6 carbon atoms, or a dialkylamino group with 2 to 8 carbon atoms. Examples of alkyl groups with 1 to 8 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, and octyl. Examples of alkoxy groups with 1 to 6 carbon atoms include... Examples of halogen atoms include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, dibutoxy, tributoxy, pentoxy, and hexoxy; halogen atoms include, for example, fluorine, chlorine, bromine, and iodine; alkylthio groups with 1 to 6 carbon atoms include, for example, methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, dibutylthio, tributylthio, pentoxy, and hexylthio; and dialkylamino groups with 2 to 8 carbon atoms include, for example, dimethylamino, diethylamino, dipropylamino, and dibutylamino.

[0457] As for X1, X2, X3, X4, X5, X6, X7, and X8, the dihydroxy compound of the present invention is preferably composed of hydrogen atoms, alkyl groups having 1 to 8 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, or halogen atoms, and is particularly preferred for ease of incorporation, being composed of hydrogen atoms, methyl groups, methoxy groups, or halogen atoms.

[0458] Of the ketones represented by formula (4'), the ketone represented by formula (4) is preferred.

[0459]

[0460] In the aforementioned chemical formula (4), R8 represents an alkyl group with 1 to 8 carbon atoms or a haloalkyl group with 1 to 6 carbon atoms.

[0461] X6, X7, and X8 independently represent a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a halogen atom, a nitro group, a cyano group, an alkylthio group with 1 to 6 carbon atoms, or a dialkylamine group with 2 to 8 carbon atoms.

[0462] In formula (4), R8 represents an alkyl group with 1 to 8 carbon atoms or a haloalkyl group with 1 to 6 carbon atoms. Examples of alkyl groups with 1 to 8 carbon atoms include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl. Examples of haloalkyl groups with 1 to 6 carbon atoms include chloromethyl and 2,2,2-trifluoroethyl.

[0463] As R8, the dihydroxy compound of the present invention is preferably methyl, ethyl, propyl, or butyl, which has excellent optical properties after being incorporated into the polymer of the present invention, and is particularly preferred for ease of incorporation, with methyl and ethyl being the most readily incorporated.

[0464] In formula (4), X6, X7, and X8 independently represent a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a halogen atom, a nitro group, a cyano group, an alkylthio group with 1 to 6 carbon atoms, or a dialkylamino group with 2 to 8 carbon atoms; for example, alkyl groups with 1 to 8 carbon atoms can be listed as follows: Methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, octyl; alkoxy groups having 1 to 6 carbon atoms, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, dibutoxy, tributoxy, pentoxy, hexoxy; halogen atoms, for example, fluorine, chlorine, bromine, iodine; alkylthio groups having 1 to 6 carbon atoms, for example, methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, dibutylthio, tributylthio, pentylthio, hexylthio; dialkylamino groups having 2 to 8 carbon atoms, for example, dimethylamino, diethylamino, dipropylamino, dibutylamino.

[0465] As for X6, X7, and X8, the dihydroxy compounds of the present invention are preferably hydrogen atoms, alkyl groups having 1 to 8 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, or halogen atoms, and are particularly preferred for ease of incorporation, being hydrogen atoms, methyl groups, methoxy groups, chlorine atoms, bromine atoms, or fluorine atoms.

[0466] As a specific ketone represented by formula (4), the structures shown by the following chemical formulas (4-1-1) to (4-2-13) can be exemplified.

[0467] [Chemistry 137]

[0468] Among these (4-1-1) to (4-2-13), the dihydroxy compound of the present invention is preferably (4-1-1) to (4-1-13) and particularly preferably (4-1-1) to (4-1-6) and (4-1-13) for its excellent optical properties after being introduced into the polymer of the present invention.

[0469] The ketone shown in formula (4) can be easily prepared by known methods or methods described in the literature. Alternatively, commercially available products can also be used.

[0470] The dihydroxy compound represented by formula (1') of the present invention can be synthesized by reacting the dihydroxy compound represented by the aforementioned chemical formula (3) with the ketone represented by the aforementioned chemical formula (4').

[0471]

[0472] In the method for manufacturing the dihydroxy compound shown in formula (1'), the ratio of the dihydroxy compound shown in formula (3) to the ketone shown in formula (4') is preferably in molar ratio of 1:0.8 to 1:2.2.

[0473] In the method for producing the dihydroxy compound shown in formula (1'), it is preferable to add a base to facilitate the reaction.

[0474] Examples of bases used include, for example, organic bases, inorganic bases, organometallic compounds, metal alkoxides, and metal amides.

[0475] Examples of organic bases include triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, piperidine, piperazine, pyrrolidine, morpholine, N-methylmorpholine, imidazole, and N-methylimidazolium.

[0476] Examples of inorganic bases include lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, potassium bicarbonate, sodium hydride, and potassium hydride.

[0477] Examples of organometallic compounds include n-butyllithium, dibutyllithium, tributyllithium, and phenyllithium.

[0478] Examples of metal alkoxides include sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide.

[0479] Examples of metallic amides include lithium amide, sodium amide, lithium amide diisopropylidene, lithium hexamethyldisilane azido, sodium hexamethyldisilane azido, and potassium hexamethyldisilane azido.

[0480] Among bases, inorganic bases are preferred for their better reaction performance and lower cost, with sodium hydroxide and potassium hydroxide being even better.

[0481] The amount of alkali used is preferably 3 to 10 moles of 1 mole equivalent for formula (3), and even more preferably 5 to 7 moles of alkali.

[0482] Alkalis can be used as granular, particulate, or powdered solids, depending on their properties. Additionally, these solutions can also be used without particular limitation on their concentration.

[0483] The method for producing the dihydroxy compound shown in formula (1') can be carried out in a solvent-free environment or in a solvent. There are no particular limitations on the solvent, as long as it is harmless to the reaction. Examples include halogen solvents such as dichloromethane and chloroform; ether solvents such as dioxane, tetrahydrofuran (hereinafter referred to as THF), diisopropyl ether, and cyclopentylmethyl ether; aromatic solvents such as benzene, toluene, xylene, chlorobenzene, and dichlorobenzene; acetylene solvents such as N,N-dimethylformamide (hereinafter referred to as DMF), N,N-dimethylacetamide, and N-methyl-2-pyrrolidone (hereinafter referred to as NMP); alcohol solvents such as methanol, ethanol, propanol, isopropanol, and tributanol; and water. These solvents can be used alone or in mixtures of two or more. Alcohol solvents are preferred for achieving good reaction yield, with ethanol and methanol being further preferred.

[0484] The reaction temperature in the method for producing the dihydroxy compound shown in formula (1') is preferably selected from a range of -20°C to 100°C, and particularly preferably from a range of 0°C to 70°C. The reaction time is determined appropriately according to the progress of the reaction, and preferably selected from a range of 1 hour to 24 hours.

[0485] In the method for producing the dihydroxy compound shown in formula (1'), it is preferable to use an acid neutralization reaction system after the reaction is complete.

[0486] Examples of acids that can be used include hydrochloric acid, sulfuric acid, acetic acid, chloroacetic acid, and citric acid. Among these, acetic acid is preferred.

[0487] There are no particular restrictions on the amount of acid used, as long as it can neutralize the amount of base used.

[0488] The dihydroxy compound obtained by the manufacturing method of formula (1') can be purified to a suitable purity. Examples of purification methods include washing, column chromatography, reprecipitation, trituration, adsorption treatment, and recrystallization. Purification by washing, reprecipitation, recrystallization, or trituration is preferred when the amount of organic solvent used is small, and purification by trituration is further preferred for ease of operation.

[0489] Organic solvents can be used during the research and development process.

[0490] The organic solvents used in the research are not particularly limited as long as they can remove byproducts. Examples include alcohol solvents such as methanol, ethanol, and isopropanol; nitrile solvents such as acetonitrile; ester solvents such as methyl acetate, ethyl acetate, and butyl acetate; hydrocarbon solvents such as pentane, hexane, heptane, and octane; and ketone solvents such as acetone, methyl ethyl ketone, and methyl isobutyl ketone. Methanol, ethanol, ethyl acetate, or acetonitrile are preferred due to their low cost and effectiveness in removing byproducts, and two or more of these can be mixed for use.

[0491] The manufacturing method of a polymer in which at least one end is a monocarboxylic acid ester can be exemplified by a manufacturing method in which a monocarboxylic acid derivative compound represented by the following chemical formula (2-1) or (2-2) is added during the polymerization of a raw material composition containing a dihydroxy compound represented by the aforementioned chemical formula (1').

[0492]

[0493] In the aforementioned chemical formula (2-1) or (2-2), R5a, R6a, and R7 independently represent groups selected from the group consisting of alkyl groups with 1 to 20 substituted carbon atoms, cycloalkyl groups with 3 to 8 substituted carbon atoms, and aromatic groups with 3 to 12 substituted carbon atoms.

[0494] X0 indicates a base detachment.

[0495] As an alkyl group having 1 to 20 carbon atoms in R5a, R6a, and R7 in chemical formula (2-1) or (2-2), for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, tributyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, and eicosyl, among which methyl, ethyl, propyl, isopropyl, butyl, isobutyl, dibutyl, and tributyl are preferred, and methyl and ethyl are particularly preferred for ease of introduction.

[0496] Examples of cycloalkyl groups with 3 to 8 carbon atoms include cyclohexyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.

[0497] As aromatic groups with 3 to 12 carbon atoms, examples include phenyl, naphthyl, biphenyl, and pyridyl.

[0498] In chemical formula (2-2), halogen atoms can be listed as the detaching radical represented by X0. For example, fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms can be listed as halogen atoms.

[0499] Monocarboxylic acid derivatives, for example, those represented by chemical formulas (2-1) or (2-2). Specific examples of chemical formulas (2-1) include acetic anhydride, propionic anhydride, butyric anhydride, isobutyric anhydride, difluoroacetic anhydride, valeric anhydride, isovaleric anhydride, neovaleric anhydride, trifluoroacetic anhydride, hexanoic anhydride, benzoic anhydride, 3-pyridinecarboxylic anhydride, cyclohexanecarboxylic anhydride, heptanoic anhydride, chloroacetic anhydride, dichlorofluoroacetic anhydride, 2-methylbenzoic anhydride, n-octanoic anhydride, 4-methoxybenzoic anhydride, nonanoic anhydride, dichloroacetic anhydride, trichloroacetic anhydride, pentafluoropropionic anhydride, decanoic anhydride, 2-methyl-6-nitrobenzoic anhydride, lauric anhydride, 3,4,5-trimethoxybenzoic anhydride, heptafluorobutyric anhydride, etc. Preferred chemical formulas include acetic anhydride, propionic anhydride, butyric anhydride, isobutyric anhydride, valeric anhydride, isovaleric anhydride, neovaleric anhydride, trifluoroacetic anhydride, hexanoic anhydride, benzoic anhydride, cyclohexane carboxylic anhydride, heptanoic anhydride, chloroacetic anhydride, and 2-methylbenzoic anhydride; particularly preferred chemical formulas include acetic anhydride, propionic anhydride, butyric anhydride, isobutyric anhydride, valeric anhydride, isovaleric anhydride, neovaleric anhydride, hexanoic anhydride, benzoic anhydride, cyclohexane carboxylic anhydride, heptanoic anhydride, and 2-methylbenzoic anhydride; specific chemical formulas (2-2) include benzoyl fluoride, undecylfluorohexyl fluoride, acetyl fluoride, chloropropane, cyclopropane carboxychlorophenoxy ... Pentyl chloride, isopentyl chloride, neopentyl chloride, 2-chloropropyl chloride, 3-chloropropyl chloride, 2-furan chloride, cyclopentane carbochloride, hexyl chloride, 2,2-dimethylbutyric chloride, 4-methylpentyl chloride, 3,3-dimethylbutyric chloride, benzyl chloride, 4-chlorobutyric chloride, 2-thiophene carbochloride, cyclohexane carbochloride, dichloroacetylfluoride, tetrahydro-2H-pyran-4-carbochloride, heptyl chloride, p-toluenecarbochloride, o-toluenecarbochloride, m-toluenecarbochloride, 3-chloroneopentyl chloride, 5-chloropentyl chloride, bromoacetylfluoride, 3-fluorobenzyl chloride, 2-fluorobenzyl chloride, 4-fluorobenzyl chloride 3-Methyl-2-thiophene carboxylic acid chloride, n-octyl chloride, 2-propylpentyl chloride, 2-ethylhexyl chloride, 4-cyanobenzoic acid chloride, 3,5-dimethylbenzoic acid chloride, 4-methoxybenzoic acid chloride, 3-methoxybenzoic acid chloride, 2-methoxybenzoic acid chloride, 2-bromopropionic acid chloride, 3-bromopropionic acid chloride, 6-chlorofumonisin chloride, 5-chlorothiophene-2-carbochloroic acid, trichloroacetylfluoro, dodecyl chloride, 4-(trifluoromethyl)benzoic acid chloride, acetyl bromide, propionic bromide, isobutyl bromide, pentapropyl bromide, benzyl bromide, bromoacetyl bromide, 2-bromopropionic bromide, 2-bromoisobutyl bromide, 2-bromobutyric acid bromide, acetyl iodide, etc.Preferred alternatives include acetyl fluoride, chloropropane, cyclopropane carbochlorohydrin, butyric acid chloride, isobutyric acid chloride, chloroacetyl fluoride, pentachlorohydrin, isopentyl chloride, neopentyl chloride, 2-chloropropane chloride, 3-chloropropane chloride, 2-furan chloride, cyclopentane carbochlorohydrin, hexyl chloride, 2,2-dimethylbutyric acid chloride, 4-methylpentyl chloride, 3,3-dimethylbutyric acid chloride, benzoyl chloride, 4-chlorobutyric acid chloride, and cyclohexyl chloride. Alkyl chloride, dichloroacetyl fluoride, heptyl chloride, p-toluenemethyl chloride, o-toluenemethyl chloride, m-toluenemethyl chloride, 3-chloroneopentyl chloride, 5-chloropentyl chloride, bromoacetyl fluoride, 3-fluorobenzoyl chloride, 2-fluorobenzoyl chloride, 4-fluorobenzoyl chloride, n-octyl chloride, 2-propylpentyl chloride, 2-ethylhexyl chloride, 4-cyanobenzoyl chloride, 3,5- Dimethylbenzyl chloride, 4-methoxybenzyl chloride, 3-methoxybenzyl chloride, 2-methoxybenzyl chloride, 2-bromopropenyl chloride, 3-bromopropenyl chloride, trichloroacetylfluoride, dodecyl chloride, 4-(trifluoromethyl)benzyl chloride; preferably acetylfluoride, chloropropane, cyclopropanecarbamate, butyric acid chloride, isobutyric acid chloride, pentachlorochloride, isopentyl chloride, neopentyl chloride, cyclopentane. Carbonyl chloride, hexyl chloride, 2,2-dimethylbutyric chloride, 4-methylpentyl chloride, 3,3-dimethylbutyric chloride, benzyl chloride, cyclohexanecarbonyl chloride, heptacyanide, p-toluenemethyl chloride, o-toluenemethyl chloride, m-toluenemethyl chloride, n-octyl chloride, 2-propylpentyl chloride, 2-ethylhexyl chloride, 3,5-dimethylbenzyl chloride, dodecyl chloride.

[0500] The polymer of the present invention can be configured as a resin composition containing 70-99.99% by weight of the polymer of the present invention and 0.01-30% by weight of a thermal reorientation accelerator (hereinafter, sometimes also referred to as the resin composition of the present invention). This resin composition is also included in one embodiment of the present invention.

[0501] The resin composition of the present invention contains a thermal reorientation accelerator. Optical films obtained using the resin composition of the present invention, due to the increased molecular mobility caused by the thermal reorientation accelerator, can undergo polymer thermal reorientation treatment even on general-purpose resin support substrates with low heat resistance temperatures.

[0502] The thermal reorientation accelerator contained in the resin composition of the present invention is preferably of a molecular weight of 100 to 20,000, and particularly preferably of 300 to 20,000, so that it can precipitate and inhibit exudation or inhibit volatilization of the thermal reorientation accelerator at high temperature.

[0503] In the resin composition of the present invention, the mixing ratio of the polymer of the present invention to the thermal reorientation accelerator is 70-99.99% by weight of the polymer of the present invention and 0.01-30% by weight of the thermal reorientation accelerator. From the perspective of preventing the precipitation of the thermal reorientation accelerator and inhibiting exudation at high temperatures, it is further preferred to be 85-99.9% by weight of the polymer of the present invention and 0.1-15% by weight of the thermal reorientation accelerator; from the viewpoint of promoting thermal reorientation efficiency, it is particularly preferred to be 85-99.0% by weight of the polymer of the present invention and 1.0-15% by weight of the thermal reorientation accelerator. In the present invention, when the proportion of the thermal reorientation accelerator is less than 0.01% by weight, promoting thermal reorientation becomes difficult; when it is greater than 30% by weight, precipitation and exudation of the thermal reorientation accelerator are likely to occur.

[0504] Examples of thermal reorientation accelerators included in the resin composition of the present invention include plasticizers, antioxidants, and light stabilizers.

[0505] Examples of such plasticizers include, for example, carboxylic acid esters, phosphate esters, and polymeric plasticizers.

[0506] Specific examples of carboxylic acid esters include phthalates, trimellitates, benzoyltetracycline, citrates, oleates, castor oil esters, sebacic acid esters, stearates, adipates, and epoxidized esters. Among these, phthalates and adipates are preferred due to their ease of use.

[0507] Phthalate esters, for example, include those with a molecular weight of 100 to 20,000 that contain the structure shown in formula (7) below.

[0508]

[0509] (In formula (7), Ra and Rb each independently represent one of the groups selected from alkyl, aromatic, complex cyclic, polycyclic aromatic, and condensed cyclic aromatic groups with 1 to 20 carbon atoms that can be substituted. These groups may have bonds such as -O-, -(C=O)O-, -O(C=O)-, -O(C=O)-O-, -C(=O)-NH-, -NH-(C=O)-, -CH=CH-, or -C≡C-. To improve the molecular orientation of polymers with less precipitation and exudation, it is preferable that Ra and Rb each independently represent alkyl groups with 2 to 20 carbon atoms.)

[0510] Specific phthalate esters include, for example, dimethyl phthalate, diethyl phthalate, dipropyl phthalate, diisopropyl phthalate, dibutyl phthalate, diisobutyl phthalate, dipentyl phthalate, dihexyl phthalate, diheptyl phthalate, di-n-octyl phthalate, dinonyl phthalate, diisononyl phthalate, di-n-decyl phthalate, diisodecyl phthalate, dodecyl phthalate, dodecyl phthalate, dodecyl phthalate, dicyclohexyl phthalate, diphenyl phthalate, di-2-ethylhexyl phthalate, benzyl butyl phthalate, and di-2-ethylhexyl isophthalate.

[0511] Examples of trimellitic acid esters with molecular weights of 100 to 20,000 include those containing the structure shown in formula (8) below.

[0512] [Chemistry 141]

[0513] (In formula (8), R11, R12 and R13 each independently represent one of the groups consisting of alkyl, aromatic, complex cyclic, polycyclic aromatic and condensed cyclic aromatic groups with 1 to 20 carbon atoms that can be substituted. These can have bonds such as -O-, -(C=O)O-, -O(C=O)-, -O(C=O)-O-, -C(=O)-NH-, -NH-(C=O)-, -CH=CH-, or -C≡C-.)

[0514] Specific examples of trimellitic esters include, for instance, trimethyl trimellitate, triethyl trimellitate, tributyl trimellitate, tris(2-ethylhexyl)triptyl trimellitate, tri-n-octyl trimellitate, triisooctyl trimellitate, trinonyl trimellitate, triisononyl trimellitate, tri-n-decyl trimellitate, triisodecyl trimellitate, tri-hexadecyl trimellitate, tri-dodecyl trimellitate, tri(tridecyl)triptyl trimellitate, tritetradecyl trimellitate, etc.

[0515] As benzopyrene esters, for example, those with a molecular weight of 100 to 20,000 that contain the structure shown in the following formula (9) can be listed.

[0516]

[0517] (In formula (9), R14, R15, R16 and R17 each independently represent one of the groups consisting of alkyl, aromatic, complex cyclic, polycyclic aromatic and condensed cyclic aromatic groups with 1 to 20 carbon atoms that can be substituted. These groups may have bonds such as -O-, -(C=O)O-, -O(C=O)-, -O(C=O)-O-, -C(=O)-NH-, -NH-(C=O)-, -CH=CH-, or -C≡C-.)

[0518] Specific examples of pyromellitic esters include, for example, tetramethyl pyromellitic acid, tetraethyl pyromellitic acid, tetrapropyl pyromellitic acid, tetrabutyl pyromellitic acid, 2-ethylhexyl pyromellitic acid, tetra(2-ethylhexyl) pyromellitic acid, tetra-n-octyl pyromellitic acid, tetra-isooctyl pyromellitic acid, tetra-nonyl pyromellitic acid, tetra-isononyl pyromellitic acid, tetra-n-decyl pyromellitic acid, tetra-isodecyl pyromellitic acid, tetra-tetraalkyl pyromellitic acid, tetra-dodecyl pyromellitic acid, tetra-trialkyl pyromellitic acid, and tetra(tetradecyl) pyromellitic acid.

[0519] As a citrate ester, for example, those with a molecular weight of 100 to 20,000 that contain the structure shown in the following formula (10) can be listed.

[0520]

[0521] In formula (10), R18, R19, and R20 each independently represent one of the groups consisting of alkyl, aromatic ring, complex cyclic group, polycyclic aromatic group, or condensed cyclic aromatic group with 1 to 20 carbon atoms that can be substituted. These groups may have -O- group, -(C=O)O- group, -O(C=O)- group, -O(C=O)-O- group, -C(=O)-NH- group, -NH-(C=O)- group, -CH=CH- group, or -C≡C- group, etc. Bonding. Rh represents one group selected from the group consisting of hydrogen atoms, acetyl groups with 1 to 20 substituted carbon atoms, alkyl groups with 1 to 20 carbon atoms, aromatic groups, complex cyclic groups, polycyclic aromatic groups, and condensed cyclic aromatic groups. These can have bonds with -O-, -(C=O)O-, -O(C=O)-, -O(C=O)-O-, -C(=O)-NH-, -NH-(C=O)-, -CH=CH-, or -C≡C- groups, etc.

[0522] Specific examples of citrate esters include, for example, trimethyl citrate, triethyl citrate, tripropyl citrate, tributyl citrate, tripentyl citrate, trihexyl citrate, acetyl trimethyl citrate, acetyl triethyl citrate, acetyl tripropyl citrate, acetyl tributyl citrate, acetyl tripentyl citrate, acetyl trihexyl citrate, and trihexyl citrate (o-butyric acid trihexyl citrate).

[0523] As an oleate, for example, those with a molecular weight of 100 to 20,000 that contain the structure shown in the following formula (11) can be listed.

[0524]

[0525] (In formula (11), R21 represents one of the groups consisting of alkyl, aromatic ring, complex ring, polycyclic aromatic ring, or condensed aromatic ring with 1 to 20 carbon atoms that can be substituted. These may have bonds such as -O- group, -(C=O)O- group, -O(C=O)- group, -O(C=O)-O- group, -C(=O)-NH- group, -NH-(C=O)- group, -CH=CH- group, or -C≡C- group.)

[0526] Specific examples of oleate esters include, for example, methyl oleate, ethyl oleate, propyl oleate, butyl oleate, hexyl oleate, heptyl oleate, n-octyl oleate, nonyl oleate, n-decyl oleate, etc.

[0527] As ricinoleate, for example, those with a molecular weight of 100 to 20,000 containing the structure shown in formula (12) below can be listed.

[0528]

[0529] In formula (12), R22 represents one of the groups consisting of alkyl, aromatic ring, complex ring, polycyclic aromatic ring, or condensed aromatic ring with 1 to 20 carbon atoms that can be substituted. These may have bonds such as -O- group, -(C=O)O- group, -O(C=O)- group, -O(C=O)-O- group, -C(=O)-NH- group, -NH-(C=O)- group, -CH=CH- group, or -C≡C- group. R23 This refers to one group consisting of hydrogen atoms, acetyl groups with 1 to 20 substituted carbon atoms, alkyl groups with 1 to 20 carbon atoms, aromatic rings, complex rings, polycyclic aromatic rings, or condensed aromatic rings, which may have bonds of -O-, -(C=O)O-, -O(C=O)-, -O(C=O)-O-, -C(=O)-NH-, -NH-(C=O)-, -CH=CH-, or -C≡C-, etc.

[0530] Specific examples of ricinoleate esters include, for example, methyl ricinoleate, ethyl ricinoleate, propyl ricinoleate, butyl ricinoleate, pentyl ricinoleate, hexyl ricinoleate, ethyl ricinoleate, propyl ricinoleate, etc.

[0531] As sebacic acid esters, for example, those with a molecular weight of 100 to 20,000 that contain the structure shown in formula (13) below can be listed.

[0532]

[0533] (In formula (13), R24 and R25 each independently represent one of the groups consisting of alkyl, aromatic ring, complex ring, polycyclic aromatic ring, or condensed aromatic ring with 1 to 20 carbon atoms that can be substituted. These may have bonds such as -O- group, -(C=O)O- group, -O(C=O)- group, -O(C=O)-O- group, -C(=O)-NH- group, -NH-(C=O)- group, -CH=CH- group, or -C≡C- group.)

[0534] Specific examples of sebacate esters include, for instance, dimethyl sebacate, diethyl sebacate, dipropyl sebacate, dibutyl sebacate, di(2-ethylhexyl) sebacate, di-n-octyl sebacate, diisooctyl sebacate, dinonyl sebacate, diisononyl sebacate, di-n-decyl sebacate, diisodecyl sebacate, dodecyl sebacate, dodecyl sebacate, tridecyl sebacate, tetradecyl sebacate, etc.

[0535] As stearates, for example, those with a molecular weight of 100 to 20,000 that contain the structure shown in formula (14) below can be listed.

[0536]

[0537] (In formula (14), R26 represents one of the groups consisting of alkyl, aromatic ring, complex ring, polycyclic aromatic ring, or condensed aromatic ring with 1 to 40 carbon atoms that can be substituted. These may have bonds such as -O- group, -(C=O)O- group, -O(C=O)- group, -O(C=O)-O- group, -C(=O)-NH- group, -NH-(C=O)- group, -CH=CH- group, or -C≡C- group.)

[0538] Specific examples of stearate esters include, for example, methyl stearate, ethyl stearate, propyl stearate, butyl stearate, pentyl stearate, hexyl stearate, heptyl stearate, n-octyl stearate, nonyl stearate, decyl stearate, dodecyl stearate, phenyl stearate, glycidyl stearate, methyl dichlorostearate, monostearate, tristearate, etc.

[0539] As an adipate, for example, those with a molecular weight of 100 to 20,000 that contain the structure shown in formula (15) below can be listed.

[0540]

[0541] (In formula (15), R27 and R28 each independently represent one of the groups consisting of alkyl, aromatic ring, complex ring, polycyclic aromatic ring, or condensed aromatic ring with 1 to 20 carbon atoms that can be substituted. These may have bonds such as -O- group, -(C=O)O- group, -O(C=O)- group, -O(C=O)-O- group, -C(=O)-NH- group, -NH-(C=O)- group, -CH=CH- group, or -C≡C- group. It is preferable that R27 and R28 each independently represent alkyl with 2 to 20 carbon atoms to improve the molecular orientation of polymers with less precipitation and exudation.)

[0542] Specific examples of adipate esters include, for instance, dimethyl adipate, diethyl adipate, dipropyl adipate, dibutyl adipate, diisobutyl adipate, bis[2-(2-butoxyethoxy)ethyl]adipate, di(2-ethylhexyl)adipate, di-n-octyl adipate, diisooctyl adipate, dinonyl adipate, diisononyl adipate, di-n-decyl adipate, diisodecyl adipate, dodecyl adipate, dodecyl adipate, trialkyl adipate, and tetraalkyl adipate.

[0543] Epoxidized esters refer to those with a molecular weight of 100 or higher and containing one or more epoxy groups and ester bonds, without any particular restrictions. Examples include 4,5-epoxycyclohexane-1,2-dicarboxylic acid di-2-ethylhexyl ester, 4,5-epoxycyclohexane-1,2-dicarboxylic acid di(9,10-epoxystearyl) ester, epoxidized soybean oil, epoxidized linseed oil, epoxidized fatty acid isobutyl ester, and epoxidized fatty acid 2-ethylhexyl ester.

[0544] The molecular weight of carboxylic acid esters can be 100 to 20,000, and is not limited to those shown in formulas (7) to (15). For example, dimethyl isophthalate, diethyl isophthalate, dipropyl isophthalate, dibutyl isophthalate, bis(2-ethylhexyl) isophthalate, di-n-decyl isophthalate, diisodecyl isophthalate, dodecyl isophthalate, trialkyl isophthalate, tetraalkyl isophthalate, dimethyl terephthalate, and terephthalate can be listed as examples.Diethyl terephthalate, dipropyl terephthalate, dibutyl terephthalate, bis(2-ethylhexyl) terephthalate, di-n-decyl terephthalate, diisodecyl terephthalate, dodecyl terephthalate, trialkyl terephthalate, tetraalkyl terephthalate, 4-cyclohexene-1,2-dicarboxylic acid diisodecyl ester, 4-cyclohexene-1,2-dicarboxylic acid bis(2-ethylhexyl), dimethyl succinate, diethyl succinate, dipropyl succinate, dibutyl succinate, bis(2-ethylhexyl) succinate, di-n-decyl succinate, diisodecyl succinate, dodecyl succinate Dimethyl maleate, diethyl maleate, dipropyl maleate, dibutyl maleate, bis(2-ethylhexyl) maleate, di-n-decyl maleate, diisodecyl maleate, monoalkyl maleate, diethyl maleate, trialkyl maleate, tetraalkyl maleate, dimethyl fumarate, diethyl fumarate, dipropyl fumarate, dibutyl fumarate, bis(2-ethylhexyl) fumarate, di-n-decyl fumarate, diisodecyl fumarate, monoalkyl fumarate, diethyl fumarate, trialkyl fumarate, diethyl fumarate, dibutyl fumarate, di(2-ethylhexyl) fumarate, di-n-decyl fumarate, diisodecyl fumarate, monoalkyl fumarate, trialkyl fumarate Tetraalkyl fumarate, dimethyl succinate, diethyl succinate, dipropyl succinate, dibutyl succinate, bis(2-ethylhexyl) succinate, di-n-decyl succinate, diisodecyl succinate, tetraalkyl succinate, tetraalkyl succinate, trialkyl succinate, tetraalkyl succinate, dimethyl azelaate, diethyl azelaate, dipropyl azelaate, dibutyl azelaate, bis(2-ethylhexyl) azelaate, di-n-decyl azelaate, diisodecyl azelaate, tetraalkyl azelaate, tetraalkyl azelaate, trialkyl azelaate, tetraalkyl azelaate, di-dodecanoate Methyl ester, diethyl dodecanoate, dipropyl dodecanoate, dibutyl dodecanoate, bis(2-ethylhexyl) dodecanoate, di-n-decanoate, diisodecanoate, dodecanoate, dodecanoate, tridecanoate, tetraalkyl dodecanoate, dimethyl tetradecanoate, diethyl tetradecanoate, dipropyl tetradecanoate, dibutyl tetradecanoate, bis(2-ethylhexyl) tetradecanoate, di-n-decanoate, diisodecanoate, dodecanoate, dodecanoate, tridecanoate, tetradecanoic acid, dimethyl hexadecanoateEster, Diethyl hexadecanoate, Dipropyl hexadecanoate, Dibutyl hexadecanoate, Di(2-ethylhexyl) hexadecanoate, Di(n-decyl) hexadecanoate, Diisodecyl hexadecanoate, Dodecyl hexadecanoate, Dodecyl hexadecanoate, Tridecyl hexadecanoate, Hexadecanoic acid, Dimethyl octadecanoate, Diethyl octadecanoate, Dipropyl octadecanoate, Dibutyl octadecanoate, Di(2-ethylhexyl) octadecanoate, Di(n-decyl) octadecanoate, Diisodecyl hexadecanoate Decyl ester, octadecanoic acid dodecyl ester, octadecanoic acid tridecyl ester, octadecanoic acid tetradecyl ester, dimethyl eicosanoate, diethyl eicosanoate, dipropyl eicosanoate, dibutyl eicosanoate, bis(2-ethylhexyl) eicosanoate, di-n-decyl eicosanoate, diisodecyl eicosanoate, octadecanoic acid dodecyl eicosanoate, octadecanoic acid tridecyl eicosanoate, octadecanoic acid tetradecyl ester, etc.

[0545] As phosphate esters, compounds represented by the following formula (16) can be listed.

[0546]

[0547] (In formula (16), R29, R30, and R31 each independently represent one of the groups consisting of alkyl, aromatic ring, complex ring, polycyclic aromatic ring, or condensed aromatic ring with 1 to 20 carbon atoms that can be substituted. These may have bonds such as -O- group, -(C=O)O- group, -O(C=O)- group, -O(C=O)-O- group, -C(=O)-NH- group, -NH-(C=O)- group, -CH=CH- group, or -C≡C- group. It is preferable that R29 to R31 each independently represent alkyl with 3 to 20 carbon atoms to improve the molecular orientation of the polymer with less precipitation and exudation.)

[0548] Specific examples of phosphate esters include, for instance, trimethyl phosphate, triethyl phosphate, tripropyl phosphate, tributyl phosphate, tripentyl phosphate, trihexyl phosphate, triheptyl phosphate, trioctyl phosphate, trinonyl phosphate, tridecyl phosphate, 2-ethylhexyl phosphate, 2-butoxyethyl phosphate, 2-chloroethyl phosphate, 1,3-dichloro-2-propyl phosphate, 2-ethylhexyl diphenyl phosphate, triphenyl phosphate, tri(xylene) phosphate, cresol diphenyl phosphate, 2-ethylhexyl phosphate, and tricresyl phosphate.

[0549] Specific examples of polymer-based plasticizers include polyester-based plasticizers and ether-based plasticizers.

[0550] Polyester plasticizers refer to polymers containing the constituent units shown in formula (17) below, with a molecular weight of 100 to 20,000.

[0551]

[0552] (In formula (17), R32 and R33 each independently represent one of the groups consisting of alkyl, aromatic ring, complex ring, polycyclic aromatic ring, or condensed aromatic ring with 1 to 20 carbon atoms that can be substituted. These may have bonds such as -O- group, -(C=O)O- group, -O(C=O)- group, -O(C=O)-O- group, -C(=O)-NH- group, -NH-(C=O)- group, -CH=CH- group, or -C≡C- group.)

[0553] Specific examples of polyester plasticizers include ADEKACIZER PN-160, PN-9302, PN-150, PN-170, PN-7230, PN-1010, PN-1020, P-200, PN-650, PN-7650, PN-1030, PN-1430, HPN-3130, PN-400, P-5040, PN-7250, PN-250, PN-7220, and PN-75. 50, PN-446, PN-310, P-300, PN-280, PN-5090 (all trade names, manufactured by ADEKA), D620, D623, D643, D645, D633, D620N, D623N, D643D, D640A, D671N (all trade names, manufactured by Mitsubishi Chemical), POLYCIZER W-230-H, W-1430-EL, W-2050, W-2310 (all trade names, manufactured by DIC), etc.

[0554] Ether-based plasticizers refer to those containing the constituent units shown in the following formula (18) with a molecular weight of 100 to 20,000.

[0555]

[0556] (In formula (18), R34 represents one of the groups consisting of alkyl chains, aromatic rings, complex rings, polycyclic aromatic rings, or condensed aromatic rings with 1 to 20 carbon atoms that can be substituted. These may have bonds such as -O- group, -(C=O)O- group, -O(C=O)- group, -O(C=O)-O- group, -C(=O)-NH- group, -NH-(C=O)- group, -CH=CH- group, or -C≡C- group.)

[0557] Specific examples of ether-based plasticizers include, for instance, ADEKACIZER RS-107, RS-700, RS-735, RS-966, RS-1000 (all trade names, manufactured by ADEKA (stock company)), MONOCIZER W-260, W-262 (all trade names, manufactured by DIC (stock company)), diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, hexaethylene glycol, heptaethylene glycol, octaethylene glycol, nonethylene glycol, decaethylene glycol, dodecaethylene glycol, polyethylene glycol 200, polyethylene glycol 400, polyethylene glycol 300, polyethylene glycol 600, polyethylene glycol 1000, polyethylene glycol 2000, polyethylene glycol 4000, polyethylene glycol 6000, polyethylene glycol 11000, polyethylene glycol 20000, etc.

[0558] As antioxidants, examples include phenolic antioxidants, amine antioxidants, phosphorus antioxidants, sulfur antioxidants, lactone antioxidants, hydroxylamine antioxidants, vitamin E antioxidants, etc.

[0559] Phenolic antioxidants refer to those with a molecular weight of 100 to 20,000 that include the structure shown in formula (19) below.

[0560]

[0561] In formula (19), at least one of R35 and R39 is selected from a group consisting of substituted secondary alkyl groups with 3 to 20 carbon atoms, tertiary alkyl groups with 4 to 20 carbon atoms, thioether groups with 6 to 20 carbon atoms, alicyclic hydrocarbons, aromatic rings, polycyclic aromatic rings, or condensed aromatic rings, which may have -O- group, -(C=O)O- group, -O(C=O)- group, or -O(C=O)- group. The other party represents a bond consisting of -O- group, -C(=O)-NH- group, -NH-(C=O)- group, -CH=CH- group, or -C≡C- group, etc., and is selected from one of the groups consisting of hydrogen atom, alkyl group with 1 to 20 substituted carbon atoms, alkoxy group with 1 to 20 carbon atoms, thioether group with 1 to 20 carbon atoms, alicyclic carbonyl group, aromatic ring, polycyclic aromatic ring, or condensed aromatic ring. These can have bonds with -O-, -(C=O)O-, -O(C=O)-, -O(C=O)-O-, -C(=O)-NH-, -NH-(C=O)-, -CH=CH-, or -C≡C- groups, etc. The structure is not particularly limited, but a third butyl group is preferred for ease of understanding. R36~R38 independently represent the carbon atoms selected from hydrogen atoms and the carbon atoms that can be substituted. One type of group consisting of alkyl groups with 1 to 20 atoms, alkoxy groups with 1 to 20 carbon atoms, aromatic rings, complex rings, polycyclic aromatic rings, or condensed aromatic rings, which may have bonds of -O- group, -(C=O)O- group, -O(C=O)- group, -O(C=O)-O- group, -C(=O)-NH- group, -NH-(C=O)- group, -CH=CH- group, or -C≡C- group, etc.

[0562] Specific examples of phenolic antioxidants include, for instance, Irganox 245 (bis[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionic acid][ethylbis(oxyethyl)]), Irganox 1010 (neopentetrate tetra[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]), Irganox 1035 (2,2'-thioethylbis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]), Irganox 1076 (octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate), Irganox 1098 (N,N'-(hexane-1,6-diyl)bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propane-acetylamine]), Irganox 1135 (octyl-3,5-di-tert-butyl-4-hydroxy-hydrogenated cinnamic acid), Irganox 1330 (2,4,6-tris(3',5'-di-tert-butyl-4'-hydroxybenzyl)trimethylbenzene), Irganox 1520 (2,4-bis(octylthiomethyl)-6-methylphenol), Irganox 259 (1,6-hexanediol bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]), Irganox 3114 (1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione), Irganox 565 (4-[[4,6-bis(octylthio)-1,3,5-triazin-2-yl]amino]-2,6-di-tert-butylphenol) (all of the above are trade names, manufactured by BASF JAPAN), tetra[3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionic acid], bis[3-[3-(tert-butyl)-4-hydroxy-5-tolyl]propaneic acid]2,4,8,10-tetraoxospiro[5,5]undecane-3,9-diylbis(2-methylpropane-2,1-diyl), etc.

[0563] Phenolic antioxidants can have a molecular weight of 100 to 20,000 and are not limited to those shown in formula (15). Examples include galvinoxyl radical, 3,3',5,5'-tetra-tert-butyl-4,4'-stilbenequinone, and 4-(hexyloxy)-2,3,6-trimethylphenol.

[0564] Amine antioxidants, for example, include those with a molecular weight of 100 to 20,000 containing the structure shown in formula (20) below.

[0565]

[0566] (In formula (20), R40 represents a ring selected from the group consisting of aromatic rings, polycyclic aromatic rings, or condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are designated as the atoms constituting the ring. These aromatic rings, polycyclic aromatic rings, and condensed aromatic rings may have substituents. R41 represents one of the group consisting of alkyl groups, aromatic rings, complex rings, polycyclic aromatic rings, or condensed aromatic rings with 1 to 20 carbon atoms that can be substituted. These may have bonds such as -O- group, -(C=O)O- group, -O(C=O)- group, -O(C=O)-O- group, -C(=O)-NH- group, -NH-(C=O)- group, -CH=CH- group, or -C≡C- group. To improve the molecular orientation of polymers with less precipitation and exudation, R41 preferably has 9 to 20 carbon atoms.)

[0567] Specific examples of amine antioxidants represented by formula (20) include, for example, 6-ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline, N-phenyl-1-naphthylamine, N,N'-di-di-butyl-1,4-phenylenediamine, 4-isopropylaminodiphenylamine, N,N'-diphenyl-1,4-phenylenediamine, N-(1,3-dimethylbutyl)-N'-phenyl-N,N'-phenylenediamine, N,N'-di-2-naphthyl-1,4-phenylenediamine, 4,4'-bis(α,α-dimethylbenzyl)diphenylamine, etc.

[0568] Amine antioxidants can have a molecular weight of 100 to 20,000 and are not limited to those shown in formula (20). Examples include 6-ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline and poly(2,2,4-trimethyl-1,2-dihydroquinoline).

[0569] As phosphorus-based antioxidants, for example, those with a molecular weight of 100 to 20,000 that contain the structure shown in the following formula (21) can be listed.

[0570]

[0571] In formula (21), R42 and R43 each independently represent one group selected from alkyl, aromatic ring, complex ring, polycyclic aromatic ring, or condensed aromatic ring with 1 to 20 carbon atoms that can be substituted, which may have bonds such as -O- group, -(C=O)O- group, -O(C=O)- group, -O(C=O)-O- group, -C(=O)-NH- group, -NH-(C=O)- group, -CH=CH- group, or -C≡C- group. R44 represents an alkyl, carbon, aromatic ring, complex ring, polycyclic aromatic ring, or condensed aromatic ring selected from alkyl, carbon, aromatic ring, or condensed aromatic ring with 1 to 20 carbon atoms that can be substituted. One type of group consisting of alkoxy groups, aromatic rings, complex rings, polycyclic aromatic rings, or condensed aromatic rings with 1 to 20 atoms, which may have bonds of -O-, -(C=O)O-, -O(C=O)-, -O(C=O)-O-, -C(=O)-NH-, -NH-(C=O)-, -CH=CH-, or -C≡C-. Preferably, R42, R43, and R44 independently represent the number of carbon atoms from 3 to 20, with the aim of improving the molecular orientation of polymers with less precipitation and exudation.

[0572] Specific examples of phosphorus-based antioxidants include trimethyl phosphite, triethyl phosphite, tripropyl phosphite, tributyl phosphite, triphenyl phosphite, trihexyl phosphite, tri-o-tolyl phosphite, tri-m-tolyl phosphite, tri-p-tolyl phosphite, succinate (2-ethylhexyl) phosphite, trioctyl phosphite, triisodecyl phosphite, succinate (1,1,1,3,3,3-hexafluoro-2-propyl) phosphite, 3,9-bis(2,4-di-tert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosspiro[5.5]undecane, succinate (2,4-di-tert-butylphenyl) phosphite, and trioleate phosphite.

[0573] As sulfur-based antioxidants, for example, those with a molecular weight of 100 to 20,000 that contain the structure shown in the following formula (22) can be listed.

[0574] [Chemical 155]R45-S─R46 (22)

[0575] In formula (22), R45 represents one group selected from alkyl, complex ring, aromatic ring, polycyclic aromatic ring, or condensed aromatic ring with 1 to 20 substituted carbon atoms, which may have -O- group, -(C=O)O- group, -O(C=O)- group, -O(C=O)-O- group, -C(=O)-NH- group, -NH-(C=O)- group, -CH=CH- group, or -C≡C- group, etc. R46 represents a group selected from hydrogen atoms with 1 to 2 substituted carbon atoms. One type of group consisting of alkyl, aromatic, complex, polycyclic aromatic, or condensed aromatic rings, which may have bonds of -O-, -(C=O)O-, -O(C=O)-, -O(C=O)-O-, -C(=O)-NH-, -NH-(C=O)-, -CH=CH-, or -C≡C-. For the purpose of improving the molecular orientation of polymers with less precipitation and exudation, it is preferable to use R45 and R46 to independently represent the number of carbon atoms from 6 to 20.

[0576] Specific examples of sulfur-based antioxidants include, for instance, 3,3'-thiodipropionate docosyl ester, 3,3'-thiodipropionate docosyl ester, and tetra[3-(dodecylthio)propionate]neopentyl tertrol.

[0577] As a light stabilizer, hindered amine light stabilizers can be cited as an example.

[0578] As hindered amine light stabilizers, for example, those having a molecular weight of 100 to 20,000 with the constituent units shown in the following formula (23) can be cited.

[0579]

[0580] In formula (23), S1 represents one of the groups consisting of -O-, -C(=O)-, and -NR47-. Here, R47 represents one of the groups consisting of hydrogen atoms or alkyl groups having 1 to 5 substituted carbon atoms. R48, R49, R50, and R51 each independently represent one of the groups consisting of alkyl groups having 1 to 20 substituted carbon atoms, complex rings, aromatic rings, polycyclic aromatic rings, or condensed aromatic rings, which may have -O-, -(C=O)O-, -O(C=O)-, -O(C=O)-O-, -C(=O)-NH-, -NH- (C=O)- group, -CH=CH- group, or -C≡C- group, etc. Among these, methyl group is particularly preferred due to its ease of use. R52 indicates one of the groups selected from hydrogen atoms, alkyl groups with 1 to 20 substituted carbon atoms, alkoxy groups with 1 to 20 carbon atoms, aromatic rings, complex rings, polycyclic aromatic rings, or condensed aromatic rings, which may have -O- group, -(C=O)O- group, -O(C=O)- group, -O(C=O)-O- group, -C(=O)-NH- group, -NH-(C=O)- group, -CH=CH- group, or -C≡C- group, etc.

[0581] Specific examples of hindered amine-based photostable agents include, for instance, 2,2,6,6-tetramethyl-4-piperidinyl methacrylate, 1,2,2,6,6-pentamethyl-4-piperidinyl methacrylate, N,N'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine, and N,N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)m-phenylene oxide. Methamide, sebacate bis(2,2,6,6-tetramethyl-4-piperidinyl) ester, sebacate bis(2,2,6,6-tetramethyl-4-piperidinyl-1-oxy) ester, sebacate bis(1,2,2,6,6-pentamethyl-4-piperidinyl) ester, butyl(3,5-di-tert-butyl-4-hydroxybenzyl)malonate bis(1,2,2,6,6-pentamethyl-4-piperidinyl) ester, etc.

[0582] Among these thermal reorientation accelerators, plasticizers are preferred due to their ease of use, good compatibility with polymers, and particularly excellent thermal reorientation accelerator properties when containing polymers.

[0583] To reduce the unevenness of the resulting film thickness, the resin composition of the present invention may contain at least one type of surfactant. Examples of surfactants that may be included include alkyl carboxylates, alkyl phosphates, alkyl urethanes, fluoroalkyl carboxylates, fluoroalkyl phosphates, fluoroalkyl urethanes, polyoxyethylene derivatives, fluoroalkyl ethylene oxide derivatives, polyethylene glycol derivatives, alkylammonium salts, and fluoroalkylammonium salts, with fluorinated surfactants being particularly preferred.

[0584] The resin composition of the present invention may also contain other polymers, high molecular weight electrolytes, conductive complexes, pigments, dyes, antistatic agents, anti-adhesion agents, lubricants, etc., within the scope not exceeding the spirit of the invention.

[0585] The resin composition of the present invention can be obtained by mixing a polymer having photoreactive reverse wavelength dispersing units that exhibit both photoreactivity and birefringence with a thermal reorientation promoter (hereinafter also referred to as a polymer, etc.).

[0586] As mixing methods, methods such as melt mixing and solution mixing can be used. Melt mixing refers to a method of manufacturing by melting and mixing polymers by heating. Solution mixing refers to a method of dissolving and mixing polymers in a solvent. For example, halogen solvents such as 1,1,1,3,3,3-hexafluoroisopropanol, dichloromethane, and chloroform can be used; aromatic solvents such as toluene and xylene; ketone solvents such as cyclopentanone, acetone, methyl ethyl ketone, and methyl isobutyl ketone; alcohol solvents such as methanol, ethanol, and propanol; ether solvents such as dioxane and tetrahydrofuran; and solvents such as dimethylformamide and N-methylpyrrolidone. Polymers can be mixed after being dissolved in a solvent, or they can be dissolved in a solvent after mixing individual polymer powders or granules. The resulting mixed polymer solution can be added to a lean solvent to precipitate the resin composition, or the mixed polymer solution can be used in the manufacture of optical films.

[0587] The polymers and resin compositions of the present invention can be used as optical films. Optical films comprising the polymers or resin compositions of the present invention (hereinafter, sometimes referred to as "optical films of the present invention") are also included in one embodiment of the present invention.

[0588] The optical film of the present invention can satisfy the following formula (I).

[0589] Re(450)≦Re(550)...(I)

[0590] (In Equation (I), Re(450) represents the in-plane phase difference measured at a wavelength of 450 nm, and Re(550) represents the in-plane phase difference measured at a wavelength of 550 nm.)

[0591] Satisfying the aforementioned equation (I) means being synonymous with satisfying the following equation (II).

[0592] Re(450) / Re(550)≦1...(II)

[0593] (In Equation (II), Re(450) represents the in-plane phase difference measured at a wavelength of 450 nm, and Re(550) represents the in-plane phase difference measured at a wavelength of 550 nm.)

[0594] The optical film of the present invention can be used with a film thickness of 1 to 20 μm, depending on the purpose, and is further preferably 10 μm or less.

[0595] In the optical film of the present invention, in the optical film formed by the polymer of the present invention having a monocarboxylic acid ester at at least one end, the yellowness (YI) in a film thickness of 5 μm is preferably 5% or less, and more preferably 3% or less.

[0596] Yellowness (YI) refers to the degree to which the hue of a polymer moves away from colorless or white towards yellow, expressed in positive value. For applications in optical films, a lower yellowness (YI) is preferred.

[0597] When the resin composition of the present invention is used as an optical film, the phase difference Re shown by the following mathematical formula (X) measured using a 589 nm light source increases after being treated by light irradiation and heated to 190 °C at high temperature. The phase difference Re is preferably 5 to 400, more preferably 5 to 300, and particularly preferably 5 to 150.

[0598] Re = (ny - nx) × d (X)

[0599] (In the mathematical formula (X), nx represents the refractive index along the fast axis (the direction of minimum refractive index) in the plane, ny represents the refractive index along the slow axis (the direction of maximum refractive index) in the plane, and d represents the film thickness (nm).)

[0600] When the resin composition of the present invention is used as an optical film, the phase difference Re shown in the following mathematical formula (X) is increased by light irradiation treatment and heating and firing treatment at 150°C at high temperature and using a light source of 589nm. The phase difference Re is preferably 35~400, more preferably 35~300, and especially preferably 35~150.

[0601] Re = (ny - nx) × d (X)

[0602] (In the mathematical formula (X), nx represents the refractive index along the fast axis (the direction of minimum refractive index) in the plane, ny represents the refractive index along the slow axis (the direction of maximum refractive index) in the plane, and d represents the film thickness (nm).)

[0603] At high temperatures, the increased phase difference Re refers to, more specifically, an increase of more than 1.3 times compared to before the addition of thermal reorientation promoters. This is likely because the thermal reorientation promoters enhance the molecular mobility of the polymer.

[0604] There are no particular limitations on the method for manufacturing the optical film of the present invention. For example, methods such as melt film formation and solution casting can be cited.

[0605] The melt film forming method refers to, specifically, the melt extrusion method, calendering method, hot pressing method, co-extrusion method, co-melting method, multilayer extrusion method, and blow molding method using a T-die, without any particular limitation.

[0606] Solution casting is a method in which a solution of a polymer (hereinafter sometimes referred to as the polymer) dissolved in a solvent (hereinafter referred to as "casting coating") is cast onto a support substrate, and then the solvent is removed by heating to obtain a film. Methods for casting the coating onto the support substrate include spin coating, T-die coating, doctor blade coating, rod coating, roller coating, and lip coating. In particular, the T-die method, in which the casting coating is continuously extruded from a die onto a strip or drum-shaped support substrate, is the most common in industry. Examples of support substrates used include glass substrates made of quartz glass, stainless steel, iron-type metal substrates, and polyethylene terephthalate films.

[0607] In order to reduce film thickness unevenness, the optical film of the present invention may contain at least one type of surfactant. Examples of surfactants include alkyl carboxylates, alkyl phosphates, alkyl urethanes, fluoroalkyl carboxylates, fluoroalkyl phosphates, fluoroalkyl urethanes, polyoxyethylene derivatives, fluoroalkyl ethylene oxide derivatives, polyethylene glycol derivatives, alkyl ammonium salts, and fluoroalkyl ammonium salts, with fluorinated surfactants, particularly fluoroalkyl carboxylates, fluoroalkyl phosphates, fluoroalkyl urethanes, fluoroalkyl ethylene oxide derivatives, and fluoroalkyl ammonium salts, are preferred.

[0608] In particular, the optical films of the present invention can be used as inverse wavelength dispersion films due to the phase difference exhibiting inverse wavelength dispersion.

[0609] The optical film of the present invention, after being formed by a melt film-forming method or a solution casting method, preferably exhibits a phase difference with reverse wavelength dispersion by irradiating either polarized ultraviolet light or obliquely incident ultraviolet light.

[0610] When using ultraviolet light, the wavelength of the ultraviolet light can be appropriately selected from the range of 200nm to 400nm. The amount of irradiation energy is preferably above 10mJ / cm2 and below 10000mJ / cm2, especially above 10mJ / cm2 and below 1000mJ / cm2.

[0611] In order to better exhibit the phase difference of reverse wavelength dispersion, the optical film of the present invention is preferably subjected to heat treatment after being irradiated with ultraviolet light as described above. The heat treatment temperature can be 50°C or higher and 400°C or lower.

[0612] The optical film of the present invention can be further heated by irradiation with polarized ultraviolet light or oblique incident ultraviolet light to exhibit three-dimensional refractive index anisotropy and be used as a phase retardation film.

[0613] When the optical film of the present invention is used as a phase retardation film, it can be used as a single film or as a multilayer film in which other films are laminated. Multilayer films incorporating this optical film are also included in one embodiment of the present invention.

[0614] Examples of laminated films include linear polarizing films, PET films, PEN films, PVA films, TAC films, cellulose ester films, and films formed from cyclic olefin polymers.

[0615] Multilayer films can be used as phase retardation films, polarizing plates, circular polarizing films, and liquid crystal alignment films.

[0616] [Summary]

[0617] [1] A main-chain polymer having a photoreactive reverse wavelength dispersive unit within the polymer main chain that exhibits both photoreactivity and birefringence in reverse wavelength dispersibility, wherein the aforementioned photoreactive reverse wavelength dispersive unit has the structure represented by the following chemical formula (1).

[0618] [Chemistry 157]

[0619] In the aforementioned chemical formula (1), L1 and L2 may be the same or different, representing carbonyl, ester, amide, ether or single bond.

[0620] * indicates the bonding position with other structures in the aforementioned main-chain polymer.

[0621] Ar represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are designated as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, or condensed aromatic rings may have substituents.

[0622] R0, R1, R2, R3, and R4 independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1).

[0623]

[0624] In the aforementioned chemical formula (Z1), Rz3 and Rz4 independently represent hydrogen atoms, halogen atoms, or alkyl groups with 1 to 8 carbon atoms, respectively.

[0625] Arz represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are defined as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, or condensed aromatic rings may have substituents.

[0626] The wavy line represents the bond position with respect to the portion of equation (1) other than R0, R1, R2, R3, or R4.

[0627] [2] As described in [1] above, in the aforementioned chemical formula (1), Ar is any of the following chemical formulas (Ar-1) to (Ar-7).

[0628]

[0629] In the aforementioned chemical formulas (Ar-1) to (Ar-7), X1, X2, X3, X4, X5, X6, X7, and X8 independently represent hydrogen atoms or alkyl groups with 1 to 8 carbon atoms, alkoxy groups with 1 to 6 carbon atoms, halogen atoms, nitro groups, cyano groups, alkylthio groups with 1 to 6 carbon atoms, or dialkylamine groups with 2 to 8 carbon atoms.

[0630] Re represents an alkyl group with 1 to 10 hydrogen atoms or carbon atoms.

[0631] **Indicates the bond positions with the parts of the aforementioned chemical formula (1) other than Ar.

[0632] [3] The main-chain polymer described in [1] above further has at least one structure selected from the group consisting of the following chemical formulas (2A), (2B), (2C) and (2D).

[0633]

[0634] In the aforementioned chemical formula (2A), ring C, ring D, and ring E independently represent rings selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings. Atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are designated as the atoms constituting the rings. These monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have substituents.

[0635] R5 and R6 may be the same or different, representing a group selected from the group consisting of hydrogen atoms, alkyl groups with 1 to 20 substituted carbon atoms, cycloalkyl groups with 3 to 8 substituted carbon atoms, and aromatic groups with 3 to 12 substituted carbon atoms.

[0636] n is 0 or 1.

[0637] L3 and L4 can be the same or different, representing carbonyl, ester, amide, ether, or single bonds.

[0638] *** indicates the bonding position with other structures in the aforementioned main-chain polymer.

[0639]

[0640] In the aforementioned chemical formula (2B), L9 and L10 may be the same or different, representing carbonyl, ester, amide, ether or single bond.

[0641] *** indicates the bonding position with other structures in the aforementioned main-chain polymer.

[0642]

[0643] In the aforementioned chemical formula (2C), X9 represents an alkyl chain with 1 to 10 carbon atoms and a single bond.

[0644] X10 represents -O- and -N(Rc)-.

[0645] X11 represents -O- and -N(Rd)-.

[0646] Rc and Rd can be the same or different, representing alkyl groups with 1 to 10 hydrogen atoms or carbon atoms.

[0647] L11 and L12 can be the same or different, representing carbonyl, ester, amide, ether, or single bonds.

[0648] *** indicates the bonding position with other structures in the aforementioned main-chain polymer.

[0649]

[0650] In the aforementioned chemical formula (2D), ring G represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, spirocyclic rings, and aliphatic hydrocarbon rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are designated as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, spirocyclic rings, and aliphatic hydrocarbon rings may have substituents.

[0651] L13 and L14 can be the same or different, representing single bonds and alkyl chains with 1 to 6 carbon atoms.

[0652] L15 and L16 can be the same or different, representing carbonyl, ester, amide, ether, or single bonds.

[0653] *** indicates the bonding position with other structures in the aforementioned main-chain polymer.

[0654] [4] As described in any one of [1] to [3] above, the main-chain polymer is at least one end of the main-chain polymer represented by the following chemical formula (2').

[0655]

[0656] In the aforementioned chemical formula (2'), R10 represents the group consisting of alkyl groups with 1 to 20 carbon atoms that can be substituted, cycloalkyl groups with 3 to 8 carbon atoms that can be substituted, and aromatic groups with 3 to 12 carbon atoms that can be substituted.

[0657] **Indicates the bonding position with other structures in the aforementioned main-chain polymer.

[0658] [5] A resin composition comprising: 70 to 99.99% by weight of the main-chain polymer as described in any one of [1] to [3] above, and 0.01 to 30% by weight of a thermal reorientation accelerator.

[0659] [6] A resin composition comprising: 70 to 99.99% by weight of the main-chain polymer as described in [4] above, and 0.01 to 30% by weight of a thermal reorientation accelerator.

[0660] [7] A method for manufacturing a main-chain polymer as described in any one of [1] to [3] above, wherein a raw material composition comprising a dihydroxy compound represented by the following chemical formula (1') is polymerized.

[0661]

[0662] [In the aforementioned chemical formula (1'), R0, R1, R2, R3, and R4 independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1). Ar represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are designated as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, or condensed aromatic rings may have substituents.]

[0663]

[0664] In the aforementioned chemical formula (Z1), Rz3 and Rz4 independently represent hydrogen atoms, halogen atoms, or alkyl groups with 1 to 8 carbon atoms, respectively.

[0665] Arz represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are defined as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, or condensed aromatic rings may have substituents.

[0666] The wavy line represents the bond position with respect to the portion of equation (1) other than R0, R1, R2, R3, or R4.

[0667] [8] A method for manufacturing a main-chain polymer as described in [4] above, wherein when polymerizing a raw material composition containing a dihydroxy compound represented by chemical formula (1'), a monocarboxylic acid derivative compound represented by either chemical formula (2-1) or (2-2) is added.

[0668]

[0669] [In the aforementioned chemical formula (2-1) or (2-2), R5a, R6a, and R7 independently represent groups selected from the group consisting of alkyl groups with 1 to 20 substituted carbon atoms, cycloalkyl groups with 3 to 8 substituted carbon atoms, and aromatic groups with 3 to 12 substituted carbon atoms.]

[0670] [9] An optical film comprising: a main-chain polymer as described in any one of [1] to [3] above or a resin composition as described in [5] above.

[0671]

[10] An optical film comprising: a main-chain polymer as described in [4] above or a resin composition as described in [6] above.

[0672]

[11] As described in [9] or

[10] above, the phase difference (Re) satisfies the following equation (I).

[0673] Re(450)≦Re(550)...(I)

[0674] (In Equation (I), Re(450) represents the in-plane phase difference measured at a wavelength of 450 nm, and Re(550) represents the in-plane phase difference measured at a wavelength of 550 nm.)

[0675]

[12] As described in

[10] above, the yellowness (YI) of the film with a thickness of 5 μm is less than 5%.

[0676]

[13] A method for manufacturing an optical film as described in any one of [9] to

[12] , wherein the film is irradiated with either polarized ultraviolet light or obliquely incident ultraviolet light.

[0677]

[14] The method for manufacturing an optical film as described in

[13] above further includes a heat treatment step.

[0678]

[15] A multilayer film having an optical film as described in any one of [9] to

[12] .

[0679]

[16] A dihydroxy compound represented by the following chemical formula (1').

[0680]

[0681] [In the aforementioned chemical formula (1'), R0, R1, R2, R3, and R4 independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1). Ar represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are designated as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, or condensed aromatic rings may have substituents.]

[0682]

[0683] In the aforementioned chemical formula (Z1), Rz3 and Rz4 independently represent hydrogen atoms, halogen atoms, or alkyl groups with 1 to 8 carbon atoms, respectively.

[0684] Arz represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are defined as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, or condensed aromatic rings may have substituents.

[0685] The wavy line represents the bond position with respect to the portion of equation (1) other than R0, R1, R2, R3, or R4.

[0686]

[17] A method for manufacturing a dihydroxy compound, wherein the dihydroxy compound represented by the following chemical formula (3) is reacted with the ketone represented by the following chemical formula (4') to obtain the dihydroxy compound represented by the following chemical formula (1').

[0687]

[0688] In the aforementioned chemical formula (3), R0, R1, and R7 independently represent hydrogen atoms, halogen atoms, or alkyl groups with 1 to 8 carbon atoms.

[0689] R2f represents a hydrogen atom, a halogen atom, an alkyl group with 1 to 8 carbon atoms, or a methyl group.

[0690]

[0691] In the aforementioned chemical formula (4'), R8 represents an alkyl group having 1 to 8 carbon atoms, or a haloalkyl group having 1 to 6 carbon atoms.

[0692] Ar represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are considered as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings may have substituents.

[0693]

[0694] [In the aforementioned chemical formula (1'), R0, R1, R2, R3, and R4 independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1). Ar represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are designated as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, or condensed aromatic rings may have substituents.]

[0695]

[0696] In the aforementioned formula (Z1), Rz3 and Rz4 independently represent hydrogen atoms, halogen atoms, or alkyl groups with 1 to 8 carbon atoms, respectively.

[0697] Arz represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are considered as the atoms constituting the ring. These monocyclic, polycyclic, or condensed aromatic rings may have substituents. The wavy part indicates the bond position with the portion of formula (1) other than R0, R1, R2, R3, or R4.

[0698] [Example]

[0699] The present invention will be further described in detail below with reference to embodiments, but the present invention should not be construed as being limited to these embodiments.

[0700] The compound (2”-2-1-DC) in the examples was synthesized according to the method described in Macromolecules, 2018, Vol. 51(23), pp. 9430-9441.

[0701] The compound (6'-1-DH) in the examples was synthesized according to the method described in patent 5325733.

[0702] <Determination of Nuclear Magnetic Resonance Spectroscopy>

[0703] The 1H-NMR spectrum was measured using a nuclear magnetic resonance apparatus (Nippon Electron, trade name: ECZ 400S).

[0704] <Membrane Thickness Measurement>

[0705] The membrane thickness in the examples was measured using a spectroscopic ellipsometry (JAWoollam, trade name: RC2-U).

[0706] <Evaluation of Yellowness (YI)>

[0707] In the embodiment, the yellowness (YI) was obtained by setting a 7mmφ beam attachment on a spectrophotometer (manufactured by Nippon Denshoku Kogyo, trade name: SH7000, light source D65) and measuring according to ASTM E313-05.

[0708] In the embodiments, the appearance of the membrane is visually confirmed, and those with no visible discoloration but acceptable are designated as "A", those with visible discoloration but very slight discoloration are designated as "B", and those with visible discoloration and unacceptable discoloration are designated as "C".

[0709] <Polarized ultraviolet irradiation>

[0710] In this embodiment, the polarized ultraviolet irradiation is achieved using an ultra-high pressure mercury lamp light source (Asahit beam splitter, trade name: REX-250) equipped with a bandpass filter (248nm, 313nm or 365nm), and only P-polarized light is extracted and irradiated at the corresponding wavelength polarization beam splitter.

[0711] <Heat Treatment>

[0712] The heat treatment of the membrane in the embodiments was performed using an oxidation-free, temperature-controlled inert oven (ESPEC, trade name: IPHH-202).

[0713] <Determination of Phase Difference Characteristics (Re)>

[0714] The phase difference characteristic (Re) in the examples was measured using a sample tilting automatic birefringence meter (manufactured by AXOMETRICS, trade name: AxoScan) with light at a wavelength of 589 nm.

[0715] Re=(ny-nx)×d...(III)

[0716] (In Equation (III), nx represents the refractive index along the fast axis (the direction of minimum refractive index) within the film surface, ny represents the refractive index along the slow axis (the direction of maximum refractive index) within the film surface, and d (nm) represents the thickness of the film.)

[0717] <Determination of Wavelength Dispersion Characteristics (Re(450) / Re(550))>

[0718] The wavelength dispersion characteristic (Re(450) / Re(550)) in the embodiment is calculated as the ratio of the in-plane phase difference Re(450) of light with a wavelength of 450 nm to the in-plane phase difference Re(550) of light with a wavelength of 550 nm, as measured using a sample tilting automatic birefringence meter (manufactured by AXOMETRICS, trade name: AxoScan).

[0719] [Example 1 of dihydroxy compounds]

[0720]

[0721] 2,5-Dihydroxybenzaldehyde (5.00 g, 36.2 mmol) and 2-acetylthiophene (4.57 g, 36.2 mmol) were dissolved in ethanol (36 mL), and then an aqueous solution of potassium hydroxide (11.0 g, 195 mmol) was added dropwise (7.4 mL) under ice-cold conditions. The reaction mixture was stirred at room temperature for 3 hours, and then acetic acid (13.0 mL, 228 mmol) was added under ice-cold conditions. The resulting reaction mixture was added to water (100 mL), followed by dichloromethane (30 mL) and vigorous stirring. The resulting solid was filtered off and washed with dichloromethane (50 mL) and distilled water (50 mL). The solid was dried under vacuum at 60 °C for 5 hours to give 5.01 g (yield: 56%) of compound (1'-2-1) as a yellow solid.

[0722] 1H-NMR(400MHz,DMSO-d6)δ10.0-8.42(br,2H),8.17(m,1H),7.99(m,1H),7.94(d,J =15.6Hz,1H),7.62(d,J=15.6Hz,1H),7.25(m,1H),7.17(s,1H),6.63-6.76(m,2H).

[0723] [Example 2 of dihydroxy compounds]

[0724]

[0725] 2,5-Dihydroxybenzaldehyde (58.1 g, 421 mmol) and 2-acetyl-5-chlorothiophene (67.5 g, 421 mmol) were dissolved in methanol (216 mL), and then 48% sodium hydroxide aqueous solution (126 mL, 2.25 mol) was added dropwise under ice-cold conditions. The reaction system was stirred at 50 °C for 3 hours, and then acetic acid (168 mL, 2.93 mol) was added under ice-cold conditions. The resulting reaction mixture was added to water (270 mL), toluene (95 mL), and isopropanol (13.5 mL), followed by the addition of water (54 mL). The resulting solid was filtered off and washed with water (50 mL) and toluene (270 mL). The resulting solid was suspended in an acetonitrile (235 mL)-methanol (59 mL) mixture, and the system was heated in an oil bath at 70 °C and stirred for 1.5 hours. The system was then cooled again in an ice bath, and the solid produced in the system was filtered off using a Buchner funnel. Next, acetonitrile (270 mL) was passed through the upper part of the Buchner funnel to wash the solid. After drying under vacuum, 81.4 g of the compound (1'-2-2) as yellow microcrystals were obtained (yield: 69%).

[0726] 1H-NMR(400MHz,DMSO-d6)δ9.88-8.62(br,2H),8.12(d,J=4.1Hz,1H),7.95(d,J=15.8 Hz,1H),7.60(d,J=15.8Hz,1H),7.31(d,J=4.1Hz,1H),7.19(s,1H),6.75-6.68(m,2H).

[0727] [Example 3 of dihydroxy compounds]

[0728]

[0729] 2,5-Dihydroxybenzaldehyde (10.0 g, 72.4 mmol) and 2-acetyl-5-bromothiophene (14.8 g, 72.4 mmol) were dissolved in ethanol (72 mL), and then a solution of potassium hydroxide (21.9 g, 391 mmol) in water (14.8 mL) was added dropwise under ice-cold conditions. The reaction mixture was stirred at room temperature for 3 hours, and then acetic acid (26.1 mL, 456 mmol) was added under ice-cold conditions. The resulting reaction mixture was then added to water (200 mL), followed by dichloromethane (60 mL), and stirred vigorously. The resulting solid was filtered off and washed with dichloromethane (100 mL) and distilled water (100 mL). The solid was dried under vacuum at 60 °C for 5 hours to give 6.08 g of compound (1'-2-3) as a yellow solid (yield: 26%).

[0730] 1H-NMR(400MHz,DMSO-d6)δ9.45(br,1H),8.83(br,1H),7.99(d,J=4.6Hz,1H),7.85(d, J=15.8Hz,1H),7.55(d,J=15.8Hz,1H),7.15(m,1H),6.69(m,2H),6.49(d,J=4.6Hz,1H).

[0731] [Example 4 of dihydroxy compounds]

[0732]

[0733] 2,5-Dihydroxybenzaldehyde (2.00 g, 14.5 mmol) and 2-acetyl-5-methoxythiophene (2.26 g, 14.5 mmol) were dissolved in ethanol (14.4 mL), and then a solution of potassium hydroxide (4.39 g, 78.2 mmol) in water (2.8 mL) was added dropwise under ice-cold conditions. The reaction system was stirred at room temperature for 3 hours, and then acetic acid (5.22 mL, 91.2 mmol) was added under ice-cold conditions. The resulting reaction mixture was added to water (50 mL) and stirred vigorously. The resulting solid was filtered off and washed with dichloromethane (50 mL) and distilled water (100 mL). The solid was dried under vacuum at 60 °C for 5 hours to give 1.05 g of compound (1'-2-5) as a yellow solid (yield: 26%).

[0734] 1H-NMR(400MHz,DMSO-d6)δ9.46(br,1H),8.85(br,1H),7.99(d,J=4.6Hz,1H),7.85(d,J=15.8Hz ,1H),7.55(d,J=15.8Hz,1H),7.15(m,1H),6.70-6.68(m,2H),6.49(d,J=4.6Hz,1H),3.94(s,3H).

[0735] [Example 5 of dihydroxy compounds]

[0736]

[0737] 2,5-Dihydroxybenzaldehyde (2.00 g, 14.5 mmol) and 2-acetyl-5-methylthiophene (2.03 g, 14.5 mmol) were dissolved in ethanol (14.4 mL), and then a solution of potassium hydroxide (4.39 g, 78.2 mmol) in water (2.8 mL) was added dropwise under ice-cold conditions. The reaction system was stirred at room temperature for 3 hours, and then acetic acid (5.22 mL, 91.2 mmol) was added under ice-cold conditions. The resulting reaction mixture was added to water (50 mL) and stirred vigorously. The resulting solid was filtered off and washed with dichloromethane (50 mL) and distilled water (100 mL). The solid was dried under vacuum at 60 °C for 5 hours to give 1.66 g of compound (1'-2-6) as a yellow solid (yield: 44%).

[0738] 1H-NMR(400MHz,DMSO-d6)δ9.92-8.58(br,2H),7.99(d,J=3.9Hz,1H),7.89(d,J=15.8H z,1H),7.56(d,J=15.8Hz,1H),7.14(m,1H),6.96(d,J=3.9Hz,1H),6.73-6.67(m,2H),2.49(s,3H).

[0739] [Example 6 of dihydroxy compounds]

[0740]

[0741] 2,5-Dihydroxybenzaldehyde (1.00 g, 7.24 mmol) and 2-acetyl-5-methylfuran (899 mg, 7.24 mmol) were dissolved in ethanol (7.2 mL), and then potassium hydroxide (2.19 g, 39.1 mmol) in water (1.4 mL) was added dropwise under ice-cold conditions. The reaction system was stirred at room temperature for 3 hours, and then acetic acid (2.61 mL, 45.6 mmol) was added under ice-cold conditions. The resulting reaction mixture was added to water (50 mL) and stirred vigorously. The resulting solid was filtered off and washed with dichloromethane (50 mL) and distilled water (100 mL). The solid was dried under vacuum at 60 °C for 5 hours to give 1.07 g (yield: 61%) of compound (1'-2-6-Furan) as a yellow solid.

[0742] 1H-NMR(400MHz,DMSO-d6)δ9.53(br,1H),8.87(br,1H),7.89(d,J=16.0Hz,1H),7.57(d,J=3.5Hz ,1H),7.42(d,J=16.0Hz,1H),7.10(m,1H),6.72-6.66(m,2H),6.37(d,J=3.5Hz,1H),2.36(s,3H).

[0743] [Example 7 of dihydroxy compounds]

[0744] [Chemistry 180]

[0745] 2,5-Dihydroxybenzaldehyde (4.49 g, 32.3 mmol) and 2-acetyl-4-methyl-5-chlorothiophene (5.65 g, 32.3 mmol) were dissolved in methanol (16 mL), and then 48% sodium hydroxide aqueous solution (10 mL, 180 mmol) was added dropwise under ice-cold conditions. The reaction system was stirred at room temperature for 4 hours, and then acetic acid (17 mL, 297 mmol) was added under ice-cold conditions. Water (30 mL) was added to the resulting reaction mixture, and the mixture was stirred vigorously. The resulting solid was filtered off and washed with hexane (100 mL) and distilled water (100 mL). The resulting solid was dried under vacuum at 50 °C for 5 hours to give 7.51 g of compound (1'-2-7) as an orange solid (yield: 79%).

[0746] 1H-NMR(400MHz,DMSO-d6)δ9.60(br,1H),9.02(br,1H),8.16(s,1H),7.98(d,J=1 5.6Hz,1H),7.62(d,J=15.6Hz,1H),7.23(m,1H),6.79-6.74(m,2H),2.23(s,3H).

[0747] [Example 8 of dihydroxy compounds]

[0748]

[0749] 2,5-Dihydroxy-4-methylbenzaldehyde (1.84 g, 12.1 mmol) and 2-acetyl-5-chlorothiophene (2.50 g, 15.5 mmol) were dissolved in methanol (16 mL), and then 48% sodium hydroxide aqueous solution (3.7 mL, 66.1 mmol) was added dropwise under ice-cold conditions. The reaction system was stirred at room temperature for 6.5 hours, and then acetic acid (4.8 mL, 83.7 mmol) was added under ice-cold conditions. Dichloromethane (10 mL) and water (34 mL) were added to the resulting reaction mixture, and the mixture was stirred vigorously. The resulting solid was filtered off and washed with distilled water (50 mL) and a mixed solution of dichloromethane and methanol (10 mL, volume ratio: dichloromethane / methanol = 5 / 1). The resulting solid was dried under vacuum at 50 °C for 3 hours to give 1.67 g (yield: 47%) of compound (1'-2-10) as a yellow solid.

[0750] 1H-NMR(400MHz,DMSO-d6)δ9.62(br,1H),8.78(br,1H),8.05(d,J=4.2Hz,1H),7.96(d,J=15.6 Hz,1H),7.51(d,J=15.6Hz,1H),7.34(d,J=4.2Hz,1H),7.12(s,1H),6.66(s,1H),2.10(s,3H).

[0751] [Example 9 of dihydroxy compounds]

[0752]

[0753] 4-Chloro-2,5-dihydroxybenzaldehyde (2.59 g, 15.0 mmol) and 2-acetyl-5-chlorothiophene (2.14 g, 15.0 mmol) were dissolved in methanol (15 mL), and then 48% sodium hydroxide aqueous solution (4.5 mL, 80.4 mmol) was added dropwise under ice-cold conditions. The reaction system was stirred at room temperature for 4 hours, and then acetic acid (6.0 mL, 105 mmol) was added under ice-cold conditions. Water (15 mL) and toluene (3.4 mL) were added to the resulting reaction mixture, and the mixture was stirred vigorously. The resulting solid was filtered off and washed with distilled water (50 mL) and a mixed solution of dichloromethane and methanol (10 mL, volume ratio: dichloromethane / methanol = 50 / 1). The resulting solid was dried under vacuum at 50 °C for 3 hours to give 1.85 g (yield: 39%) of compound (1'-2-11) as a yellow solid.

[0754] 1H-NMR(400MHz,DMSO-d6)δ9.95(br,1H),9.61(br,1H),8.11(d,J=4.2Hz,1H),7.91(d, J=15.7Hz,1H),7.63(d,J=15.7Hz,1H),7.37(s,1H),7.36(d,J=4.2Hz,1H),6.90(s,1H).

[0755] [Dihydroxy compound, Example 10]

[0756]

[0757] 2,5-Dihydroxyterephthalaldehyde (1.29 g, 7.74 mmol) and 2-acetyl-5-chlorothiophene (2.49 g, 15.5 mmol) were dissolved in methanol (12 mL), and then 48% sodium hydroxide aqueous solution (1.8 mL, 32.1 mmol) was added dropwise under ice-cold conditions. The reaction system was stirred at room temperature for 2.5 hours, and then acetic acid (3.1 mL, 54.1 mmol) was added under ice-cold conditions. Dichloromethane (6.5 mL) and water (22 mL) were added to the resulting reaction mixture, and the mixture was stirred vigorously. The resulting solid was filtered off and washed with distilled water (50 mL) and methanol (6.0 mL). The resulting solid was dried under vacuum at 50 °C for 3 hours to give 2.0 g of compound (1'-7-2) as a red solid (yield: 57%).

[0758] 1H-NMR (400MHz, DMSO-d6) δ9.87(br,2H),8.11(d,J=4.2Hz,2H),7.96(d,J=15.6Hz,2H),7.66(d,J=15.6Hz,2H),7.37(d,J=4.2Hz,2H),7.30(s,2H).

[0759] [Example 11 of dihydroxy compounds]

[0760] [Chemistry 184]

[0761] 2,5-bis(methoxymethoxy)benzaldehyde (4.53 g, 20.0 mmol) and 2-acetyl-1-methylpyrrole (2.35 mL, 20.0 mmol) were dissolved in methanol (10 mL), and then 48% sodium hydroxide aqueous solution (6.1 mL, 110 mmol) was added dropwise under ice-cold conditions. The reaction system was stirred at room temperature for 2 hours, then heated to 50 °C and stirred for 2 hours. After the reaction was complete, methanol (90 mL) and 10% hydrochloric acid aqueous solution (50 mL) were added under ice-cold conditions, and the mixture was stirred at 50 °C for 1 hour. The reaction solution was concentrated under reduced pressure, extracted with ethyl acetate (100 mL × 3), and the combined organic layers were washed with saturated brine (50 mL × 3) and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the crude product was washed with ethyl acetate (2.0 mL) and cold methanol (1.0 mL). The obtained solid was dried under vacuum at 50°C for 3 hours to obtain compound (1'-6-2) as a yellow solid (yield: 2.11 g, yield: 43%).

[0762] 1H-NMR(400MHz,DMSO-d6)δ9.43(brs,1H),8.86(brs,1H),7.85(d,J=15.8Hz,1H),7.50(d,J=15.8Hz,1H),7.31(dd,J=4.1,1.8Hz,1H),7 .18(t,J=1.8Hz,1H),7.13(d,J=2.7Hz,1H),6.73(d,J=8.7Hz,1H),6.69(dd,J=8.7,2.7Hz,1H),6.18(dd,J=4.1,2.5Hz,1H),3.94(s,3H).

[0763] [Example 12 of dihydroxy compounds]

[0764] [Chemistry 185]

[0765] 2,5-bis(methoxymethoxy)benzaldehyde (4.53 g, 20.0 mmol) and 2-acetyl-1-ethylpyrrole (2.72 mL, 20.0 mmol) were dissolved in methanol (10 mL), and then 48% sodium hydroxide aqueous solution (6.1 mL, 110 mmol) was added dropwise under ice-cold conditions. The reaction system was stirred at room temperature for 2 hours, then heated to 50 °C and stirred for another 2 hours. After the reaction was complete, methanol (90 mL) and 10% hydrochloric acid aqueous solution (50 mL) were added under ice-cold conditions, and the mixture was stirred at 50 °C for 1 hour. The reaction solution was concentrated under reduced pressure, extracted with ethyl acetate (100 mL × 3), and the combined organic layers were washed with saturated brine (50 mL × 2) and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure. The crude product was washed with a mixed solution of hexane and ethyl acetate (2.0 mL, volume ratio: hexane / ethyl acetate = 1 / 1) and cold methanol (1.0 mL). The resulting solid was dried under vacuum at 50 °C for 3 hours to obtain compound (1'-6-3) as a yellow solid (yield: 2.02 g, yield: 39%).

[0766] 1H-NMR(400MHz,DMSO-d6)δ9.43(brs,1H),8.86(brs,1H),7.85(d,J=15.7Hz, 1H),7.51(d,J=15.7Hz,1H),7.33(dd,J=4.1,1.7Hz,1H),7.25(dd,J=2.4,1.7 Hz,1H),7.13(d,J=2.8Hz,1H),6.73(d,J=8.6Hz,1H),6.69(dd,J=8.6,2.8Hz, 1H),6.19(dd,J=4.1,2.4Hz,1H),4.40(q,J=7.1Hz,2H),1.29(t,J=7.1Hz,3H).

[0767] [Synthesis example 1]

[0768] [Chemistry 186]

[0769] Under argon atmosphere, thionyl chloride (15.5 mL) and DMF (250 μL) were added to a toluene (25 mL) solution of 2-chloro-4-methoxybenzoic acid (5.00 g, 26.8 mmol). After stirring at 100 °C for 1 hour, excess thionyl chloride was distilled off under reduced pressure, and THF (45 mL) was added to the resulting residue. This solution was used entirely for the next reaction.

[0770] A THF (45 mL)-water (45 mL) solution of 4-(methylamino)phenol sulfate (4.61 g, 13.4 mmol) was cooled to 0 °C. Sodium bicarbonate (5.63 g, 67.0 mmol) was added while stirring, followed by the dropwise addition of a pre-prepared THF solution of the acid chloride over 5 minutes. The mixture was heated to room temperature and stirred vigorously for 1.5 hours. Concentrated hydrochloric acid (10 mL) was added, and the mixture was concentrated under reduced pressure. The solid produced in the system was filtered off and washed with water (200 mL) to obtain a crude solid. This was further purified by reprecipitation (hexane: 50 mL, ethyl acetate: 5 mL, ethanol: 3 mL) to give a white solid of 2-chloro-4'-hydroxy-4-methoxy-N-methylbenzylaniline (yield: 6.42 g, yield: 82%).

[0771] 1H-NMR (400MHz, DMSO-d6): δ9.50(brs,1H),7.16(d,J=8.6Hz,1H),6.99(d,J=8.7Hz,2H),6.85 (d,J=2.4Hz,1H),6.73(dd,J=8.6,2.4Hz,1H),6.56(d,J=8.7Hz,2H),3.69(s,3H),3.28(s,3H).

[0772] Under argon atmosphere, a suspension of 2-chloro-4'-hydroxy-4-methoxy-N-methylbenzylaniline (5.00 g, 17.1 mmol) in dichloromethane (170 mL) was cooled to 0 °C, and then a 1 M boron tribromide solution in dichloromethane (68.4 mL, 68.4 mmol) was added dropwise over 15 minutes. The reaction system was heated to room temperature and stirred for 13 hours, then cooled back to 0 °C. Ice (400 g) was added, and the mixture was stirred at room temperature until the ice dissolved. The mixture was concentrated under reduced pressure, distilled off the dichloromethane, and extracted with ethyl acetate (200 mL × 3). The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate = 5:95) and then dried under reduced pressure (120°C, vacuum pump) to give a white solid compound (2”A-1-36-DH) (yield: 3.67 g, yield: 77%).

[0773] 1H-NMR (400MHz, DMSO-d6): δ10.4-9.15(br,2H),7.02(m,1H),6.95(d,J=8.5Hz,2H),6.61(m,1H),6.56(d,J=8.5Hz,2H),6.53(m,1H),3.27(s,3H).

[0774] [Synthesis example 2]

[0775]

[0776] A mixture of 4-hydroxybenzoic acid (40.1 g, 290 mmol), thionyl chloride (276 g, 2.32 mol), and N,N-dimethylformamide (21.2 mg, 290 μmol) was heated under reflux and stirred for 1 hour. Excess thionyl chloride was then distilled off to obtain 4-hydroxybenzoic acid chloride. The obtained 4-hydroxybenzoic acid chloride was used entirely as a THF (350 mL) solution in the next reaction.

[0777] Under nitrogen, a mixture of p-methylaminophenol sulfate (50.0 g, 290 mmol), water (350 mL), and THF (350 mL) was stirred while ice-cold, and sodium bicarbonate (122 g, 1.45 mol) was added over 5 minutes. Then, a THF solution of the prepared 4-hydroxybenzoic acid chloride was added dropwise over 5 minutes. After the addition, the mixture was slowly heated to room temperature while stirring for 15 hours, and then the THF was distilled off under reduced pressure. The resulting solid was filtered, washed with water (1 L), and then washed with 2 M hydrochloric acid (600 mL) and acetonitrile (200 mL) to obtain compound (2”A-1-1-DH) as a white solid (yield: 44.3 g, 62.7%).

[0778] 1H-NMR(400MHz,DMSO-d6): δ9.97-9.22(br,2H),7.03(d,J=8.7Hz,2H),6.86 (d,J=8.7Hz,2H),6.58(d,J=8.7Hz,2H),6.50(d,J=8.7Hz,2H),3.20(s,3H).

[0779] [Synthesis example 3]

[0780] [Chemistry 188]

[0781] A mixture of vanillic acid (5.0 g, 29.7 mmol), thionyl chloride (28.3 g, 238 mol), and N,N-dimethylformamide (2.17 mg, 29.7 μmol) was heated under reflux and stirred for 1 hour. The thionyl chloride was then distilled off to obtain vanillic acid chloride. The resulting vanillic acid chloride was used as a THF (35 mL) solution entirely in the next reaction.

[0782] Under nitrogen, a mixture of p-methylaminophenol sulfate (5.12 g, 29.7 mmol), water (35 mL), and THF (35 mL) was stirred at ice temperature while sodium bicarbonate (12.5 g, 149 mol) was added over 5 minutes. Then, a THF solution of vanillic acid chloride prepared above was added dropwise over 5 minutes. After addition, the mixture was slowly heated to room temperature while stirring for 15 hours, followed by distillation off the THF under reduced pressure. The resulting mixture was extracted with ethyl acetate (50 mL × 3), and the organic layer was washed with 2 M hydrochloric acid (200 mL) and water (200 mL), then dried over anhydrous sodium sulfate. The resulting organic layer was concentrated under reduced pressure to give compound (2”A-1-6-DH) as a white solid (yield: 4.90 g, 60%).

[0783] 1H-NMR (400MHz, DMSO-d6): δ9.60-9.09(br,2H),6.90-6.84(m,2H),6.70-6.62(m,2H),6.60-6.54(m,2H),6.52(m,1H),3.51(s,3H),3.22(s,3H).

[0784] [Synthesis Example 4]

[0785] [Chemistry 189]

[0786] Under nitrogen, 4'-hydroxyacetanilide (3.85 g, 25.5 mmol) was chilled and then slowly added to a 1 mol / L borane-THF complex THF solution (100 mL, 100 mmol). The reaction system was heated to room temperature and then stirred at 60 °C for 24 hours. After the reaction was complete, the mixture was cooled in an ice bath and methanol (21 mL) was added over 5 minutes. Water (100 mL) was added to the resulting reaction mixture, and the THF was removed by distillation using an evaporator. The mixture was then extracted with dichloromethane (100 mL × 3). The resulting organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting composition was purified by silica gel column chromatography (ethyl acetate / hexane = 61 / 39 Vol%) to give 4-ethylaminophenol as a brown solid (yield: 2.07 g, yield: 59%).

[0787] 1H-NMR (400MHz, CDCl3): δ6.69(d,J=8.9Hz,2H),6.53(d,J=8.9Hz,2H),4.60-3.20(br,2H),3.09(q,J=7.2Hz,2H),1.22(t,J=7.2Hz,3H).

[0788] A mixture of 4-hydroxybenzoic acid (2.01 g, 29.7 mmol), thionyl chloride (13.9 g, 117 mmol), and N,N-dimethylformamide (1.07 mg, 14.6 μmol) was heated under reflux and stirred for 1 hour. The thionyl chloride was then distilled off to obtain 4-hydroxybenzoic acid chloride. The obtained 4-hydroxybenzoic acid chloride was used entirely as a THF (13 mL) solution in the next reaction.

[0789] Under nitrogen, a mixture of 4-ethylaminophenol (2.00 g, 14.6 mmol), water (13 mL), and THF (13 mL) was stirred at ice temperature while sodium bicarbonate (6.12 g, 72.9 mmol) was added over 5 minutes. Then, a THF solution of the prepared 4-hydroxybenzoic acid chloride was added dropwise over 5 minutes. After addition, the mixture was slowly heated to room temperature while stirring for 15 hours, followed by distillation off the THF under reduced pressure. The resulting mixture was extracted with ethyl acetate (50 mL × 3), and the organic layer was washed with 2N hydrochloric acid (100 mL × 2) and water (100 mL), then dried over anhydrous sodium sulfate. The resulting organic layer was concentrated under reduced pressure to give compound (2”A-1-2-DH) as a white solid (yield: 1.99 g, 53%).

[0790] 1H-NMR (400MHz, DMSO-d6): δ8.85-10.12(2H),7.02(d,J=8.7Hz,2H),6.83(d,J=8.7Hz,2H) ,6.59(d,J=8.7Hz,2H),6.49(d,J=8.7Hz,2H),3.70(q,J=7.2Hz,2H),1.01(t,J=7.2Hz,3H).

[0791] [Synthesis example 5]

[0792]

[0793] Under stirring, a solution of 1,4-benzoquinone (16.2 g, 150 mmol) in NMP (32.4 mL) and acetic acid (40.5 mL) was slowly added to a solution of piperidine pentamethylene dithiocarbamate (18.5 g, 75 mmol) in NMP (40.5 mL) at 15 °C. The reaction system was heated to 50 °C and stirred for 2 hours. After confirming the formation of a solid in the reaction system, it was cooled to room temperature and acetone (100 mL) was added. The solid in the system was filtered off, washed with a mixture of acetone (50 mL) and acetic acid (50 mL), and dried under reduced pressure to give 10.2 g of compound (6C) as a yellow solid (yield: 20.7%).

[0794] 1H-NMR (400MHz, CD3OD): δ6.83(s,2H),3.99-3.97(m,4H),1.98-1.92(m,7H),1.84-1.82(m,2H).

[0795] [Synthesis example 6]

[0796] [Chemistry 191]

[0797] Under nitrogen conditions, dimethyl malonate (1.5 g, 11.3 mol) was added to a 15 mL DMF solution of compound (6C) (3.7 g, 11.3 mmol) obtained in Example 5 at room temperature. The reaction system was heated to 100 °C with stirring and stirred for 6 hours. Then, the reaction system was cooled to room temperature, and water (100 mL) was added. The mixture was extracted with ethyl acetate (100 mL × 2 times), and the combined organic layers were washed with 1 N hydrochloric acid (100 mL) and saturated brine (50 mL). The organic layers were dried with sodium sulfate and then dried under reduced pressure to obtain a crude purified product. This crude purified product was purified by silica gel column chromatography (methanol:dichloromethane = 3:97~4:96) to give 950 mg of compound (6'-2-DH) as a light brown solid (yield: 4%).

[0798] 1H-NMR (400MHz, DMSO-d6): δ10.09(s,2H),6.70(s,2H),3.77(s,6H).

[0799] [Synthesis Example 7]

[0800]

[0801] Under nitrogen conditions, diethyl malonate (1.2 g, 7.40 mmol) was added to a 24 mL solution of DMF containing compound (6C) (2.4 g, 7.40 mmol) obtained in Example 5 at room temperature. The reaction system was heated to 100 °C with stirring and stirred for 6 hours. The system was then cooled to room temperature, and 100 mL of water was added. The mixture was extracted with ethyl acetate (100 mL × 2 times), and the combined organic layers were washed with 1 N hydrochloric acid (100 mL) and saturated brine (50 mL). The organic layers were dried over sodium sulfate and then dried under reduced pressure to obtain a crude purified product. This crude purified product was purified by silica gel column chromatography (methanol:dichloromethane = 3:97~4:96) to give 470 mg of compound (6'-3-DH) as a light brown solid (yield: 18%).

[0802] 1H-NMR (400MHz, CDCl3): δ10.08(s,2H),6.69(s,2H),4.22(q,J=7.2Hz,4H),1.27(t,J=7.2Hz,6H).

[0803] [Synthesis example 8]

[0804]

[0805] Under nitrogen conditions, ethyl cyanoacetate (1.5 g, 13.2 mmol) was added to a 30 mL DMF solution of compound (6C) (4.33 g, 13.2 mmol) obtained in Example 5 at room temperature. The reaction system was heated to 100 °C with stirring and stirred for 6 hours. Then, the reaction system was cooled to room temperature and water (100 mL) was added. The mixture was extracted with ethyl acetate (100 mL × 2 times), and the combined organic layers were washed with 1 N hydrochloric acid (100 mL) and saturated brine (50 mL). The organic layers were dried with sodium sulfate and then dried under reduced pressure to obtain a crude purified product. This crude purified product was purified by silica gel column chromatography (methanol:dichloromethane = 3:97~4:96) to give 950 mg of compound (6'-5-DH) as a light brown solid (yield: 24%).

[0806] 1H-NMR (400MHz, DMSO-d6): δ10.39(s,1H),10.34(s,1H),6.78(s,2H),4.25(q,J=7.2Hz,2H),1.28(t,J=7.2Hz,3H).

[0807] [Synthesis Example 9]

[0808] [Chemistry 194]

[0809] Under nitrogen conditions, methyl acetone (1.5 g, 12.9 mmol) was added to a 15 mL solution of DMF containing compound (6C) (4.22 g, 12.9 mmol) obtained in Example 5 at room temperature. The reaction system was heated to 100 °C with stirring and stirred for 6 hours. The reaction system was then cooled to room temperature, and water (100 mL) was added. The mixture was extracted with ethyl acetate (100 mL × 2 times), and the combined organic layers were washed with 1 N hydrochloric acid (100 mL) and saturated brine (50 mL). The organic layers were dried over sodium sulfate and then dried under reduced pressure to obtain a crude purified product. This crude purified product was purified by silica gel column chromatography (methanol:dichloromethane = 3:97~4:96) to give 940 mg of compound (6'-7-DH) as a light brown solid (yield: 25%).

[0810] 1H-NMR (400MHz, DMSO-d6): δ10.14(s,1H),10.12(s,1H),6.74(s,2H),3.85(s,3H),2.50(s,3H).

[0811] [Synthesis Example 10]

[0812]

[0813] In a nitrogen environment, acetone (1.5 g, 14.9 mmol) was added to a 30 mL DMF solution of compound (6C) (4.89 g, 14.9 mmol) obtained in Example 5 at room temperature. The reaction system was heated to 100 °C with stirring and stirred for 8 hours. Then, the reaction system was cooled to room temperature, and water (100 mL) was added. The mixture was extracted with ethyl acetate (100 mL × 2 times), and the combined organic layers were washed with 1 N hydrochloric acid (100 mL) and saturated brine (50 mL). The organic layers were dried with sodium sulfate and then dried under reduced pressure to obtain a crude purified product. This crude purified product was purified by silica gel column chromatography (methanol:dichloromethane = 3:97~4:96) to give 940 mg of compound (6'-6-DH) as a light brown solid (yield: 22%).

[0814] 1H-NMR (400MHz, DMSO-d6): δ10.11(s,2H),6.74(s,2H),2.61(s,6H).

[0815] [Synthesis Example 11]

[0816]

[0817] Under argon atmosphere, a mixture of 4-acetylated benzoic acid (7.56 g, 42.0 mmol), thionyl chloride (24.0 mL, 331 mmol), and N,N-dimethylformamide (catalyst amount) was refluxed and boiled for 3 hours. Volatile components were distilled off, and 4-acetylated benzoic acid chloride was obtained by azeotropic reaction with toluene (3 × 20 mL). The obtained 4-acetylated benzoic acid chloride was used entirely as a tetrahydrofuran (50 mL) solution in the next reaction.

[0818] Under argon atmosphere, methylhydrazine (1.05 mL, 19.8 mmol) and triethylamine (8.40 mL, 60.3 mmol) were dissolved in tetrahydrofuran (40 mL). A pre-prepared tetrahydrofuran solution of 4-acetoxybenzoic acid chloride was slowly added while ice-cold, and the mixture was heated to room temperature and stirred overnight. The solvent was distilled off under reduced pressure, and 1 M hydrochloric acid (100 mL) was added, followed by extraction with ethyl acetate (2 × 100 mL). The combined organic layers were washed sequentially with saturated sodium bicarbonate aqueous solution (100 mL) and saturated brine (100 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was suspended in methanol (75 mL), and a solution of sodium hydroxide (4.13 g, 103 mmol) in water (25 mL) was added, and the mixture was stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure, and 2 M hydrochloric acid (75 mL) was added, followed by extraction with ethyl acetate (2 × 100 mL). The combined organic layers were washed sequentially with water (100 mL), saturated sodium bicarbonate aqueous solution (2 × 100 mL), and saturated brine (100 mL), and then dried with anhydrous sodium sulfate. The precipitated solid was separated by filtration and washed with ethyl acetate and water to obtain a white solid compound (2”C-2-2). The organic layer was separated by the filtrate, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography. The obtained solid was washed with a slurry in diethyl ether (50 mL) to obtain a white solid compound (2”C-2-2). The total yield was 3.02 g, with a yield of 53%.

[0819] 1H-NMR (400MHz, DMSO-d6): δ10.76(brs,1H),10.12(brs,1H),9.81(brs,1H),7.66-7. 46(brm,2H),7.46-7.36(m,2H),6.82-6.73(m,2H),6.73-6.60(brm,2H),3.15(s,3H).

[0820] [Synthesis Example 12]

[0821]

[0822] Under argon atmosphere, a mixture of 4-hydroxybenzoic acid (2.49 g, 18.0 mmol), toluene (18 mL), thionyl chloride (10.5 mL, 145 mmol), and N,N-dimethylformamide (catalyst amount) was refluxed and boiled for 1 hour. The volatile components were distilled off, and 4-hydroxybenzoic acid chloride was obtained by azeotropic reaction with toluene (3 × 15 mL). The obtained 4-hydroxybenzoic acid chloride was used entirely as a tetrahydrofuran (18 mL) solution in the next reaction.

[0823] Under argon atmosphere, 4-(dodecylamino)phenol (4.16 g, 15.0 mmol) and sodium bicarbonate (2.52 g, 30.0 mmol) were suspended in a mixed solvent of tetrahydrofuran (17 mL) and water (17 mL). A pre-prepared tetrahydrofuran solution of 4-hydroxybenzoic acid chloride was slowly added under ice-cold conditions, and the mixture was heated to room temperature and stirred for 4 hours. The solvent was distilled off under reduced pressure, and the residue was extracted with water (50 mL) and ethyl acetate (3 × 50 mL). The combined organic layers were washed with saturated sodium bicarbonate aqueous solution (80 mL), 2M hydrochloric acid (80 mL), and saturated brine (80 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in methanol (50 mL), and a sodium hydroxide solution (1.21 g, 30.3 mmol) in water (10 mL) was added. After stirring at room temperature for 1 hour, the mixture was concentrated under reduced pressure. Water (35 mL) was added to the residue, the pH was adjusted to 1 with concentrated hydrochloric acid, and the residue was extracted with ethyl acetate (3 × 50 mL). The combined organic layers were washed with saturated sodium bicarbonate aqueous solution (100 mL) and saturated brine (100 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, and the resulting solid was washed with a slurry in a mixed solvent of toluene (15 mL) / hexane (15 mL) to give a grayish-white solid compound (1-1-104-DH) (yield: 4.74 g, yield: 80%).

[0824] 1H-NMR (400MHz, DMSO-d6): δ9.69(brs,1H),9.47(brs,1H),7.10-7.00(m,2H),6.92-6.80(m,2H),6.68-6.58( m,2H),6.58-6.48(m,2H),3.69(t,J=7.5Hz,2H),1.53-1.36(m,2H),1.34-1.12(m,18H),0.85(t,J=6.8Hz,3H).

[0825] [Synthesis Example 13]

[0826]

[0827] A mixture of monomethyl terephthalate (9.19 g, 50.0 mmol), thionyl chloride (59.53 g, 0.50 mol), and toluene (50 mL) was heated under reflux and stirred for 1 hour. The thionyl chloride was then distilled off to obtain methyl 4-(chloromethacryl)benzoate. The obtained methyl 4-(chloromethacryl)benzoate was used as a 50 mL THF solution entirely in the next reaction.

[0828] A mixed solution of p-methylaminophenol sulfate (8.44 g, 24.5 mmol), sodium bicarbonate (12.60 g, 0.15 mol), THF (50 mL), and water (50 mL) was cooled to 0 °C. A pre-prepared THF solution of methyl 4-(chloromethacryl)benzoate was added dropwise over 15 minutes, followed by heating to room temperature and vigorous stirring for 12 hours. After the reaction was complete, the solvent was concentrated under reduced pressure. The solid produced in the system was filtered off and washed with saturated sodium carbonate aqueous solution (50 mL) and water (50 mL) to obtain a white crude solid (crude yield: 13.53 g, crude yield: 97%).

[0829] Methanol (50 mL) and 48% sodium hydroxide aqueous solution (6.0 mL, 0.11 mol) were added to the crude solid, and the mixture was stirred at room temperature for 4 hours. After the reaction was complete, water (50 mL) was added, and the insoluble matter was separated by filtration. Concentrated hydrochloric acid was added to the filtrate to adjust the pH to 2, and the resulting solid was filtered off. Reprecipitation by ethyl acetate / hexane yielded a white solid compound (2”A-1-1-CH) (yield: 11.67 g, total yield: 83%).

[0830] 1H-NMR(400MHz,(DMSO-d6:δ13.01(brs,1H),9.53(s,1H),7.74(d,J=7.3Hz,2H), 7.32(d,J=7.3Hz,2H),6.96(d,J=7.8Hz,2H),6.60(d,J=7.8Hz,2H),3.31(s,3H).

[0831] [Synthesis Example 14]

[0832]

[0833] A mixed solution of 4-(ethylamino)phenol (4.84 g, 25.0 mmol), sodium bicarbonate (4.21 g, 50.1 mmol), THF (30 mL), and water (60 mL) was cooled to 0 °C. A solution of 4-(chloromethacryl)benzoate methyl ester (5.24 g, 25.1 mmol) in THF (30 mL) was added dropwise over 15 minutes. The mixture was then heated to room temperature and stirred vigorously for 12 hours. After the reaction was complete, the solvent was concentrated under reduced pressure. The solid produced in the system was filtered off and washed with saturated sodium carbonate aqueous solution (50 mL) and water (50 mL) to obtain a brown crude solid (crude yield 7.93 g, crude yield 89%).

[0834] Methanol (80 mL) and water (80 mL) were added to the obtained crude solid. After cooling to 0 °C, 4.0 mL (72.3 mmol) of 48% sodium hydroxide aqueous solution was added, and the reaction system was heated to room temperature and refluxed for 4 hours. After the reaction was completed, the mixture was cooled to room temperature and concentrated under reduced pressure. Concentrated hydrochloric acid was added to the residue to adjust the pH to 2. The resulting solid was filtered off and dried under reduced pressure to obtain a brown solid compound (2”A-1-2-CH) (yield: 6.93 g, 97% total yield).

[0835] 1H-NMR (400MHz, DMSO-d6): δ12.99(brs,1H),9.52(s,1H),7.73(d,J=7.8Hz,2H),7.31(d,J=7.8H z,2H),6.92(d,J=8.2Hz,2H),6.60(d,J=8.2Hz,2H),3.80(q,J=7.0Hz,2H),1.09(t,J=7.0Hz,3H).

[0836] [Synthesis Example 15]

[0837]

[0838] A mixed solution of 3-methyl-4-(methylamino)phenol (2.06 g, 15.0 mmol), sodium bicarbonate (2.52 g, 30.0 mol), THF (30 mL), and water (15 mL) was cooled to 0 °C. A solution of methyl 4-(chloromethacryl)benzoate in THF (15 mL) was added dropwise over 15 minutes, followed by warming to room temperature and vigorous stirring for 12 hours. After the reaction was complete, the solvent was concentrated under reduced pressure and extracted with ethyl acetate (50 mL × 3). The combined organic phases were washed with saturated sodium carbonate aqueous solution (50 mL) and saturated brine (50 mL), dehydrated with magnesium sulfate, and concentrated under reduced pressure to obtain a white crude solid (crude yield: 3.76 g, crude yield: 84%).

[0839] Methanol (40 mL) and water (40 mL) were added to the crude solid, followed by 3.2 mL (57.9 mmol) of 48% sodium hydroxide aqueous solution. The mixture was stirred under reflux for 1 hour at room temperature for 12 hours. After the reaction was complete, the mixture was concentrated under reduced pressure. The residue was treated with concentrated hydrochloric acid to adjust the pH to 2. The resulting solid was filtered off and reprecipitated by ethyl acetate / hexane to give a white solid compound (2”A-1-46-CH) (yield: 3.49 g, total yield: 82%).

[0840] 1H-NMR (400MHz, DMSO-d6): δ13.05(brs,1H),9.45(s,1H),7.73(d,J=8.5Hz,2H),7.31(d,J=8.5Hz,2H ),6.99(d,J=8.4Hz,1H),6.49(d,J=2.8Hz,1H),6.46(dd,J=8.4,2.8Hz,1H),3.21(s,3H),2.05(s,3H).

[0841] [Synthesis Example 16]

[0842]

[0843] A mixed solution of 4-(ethylamino)-3-methylphenol (3.02 g, 20.0 mmol), sodium bicarbonate (3.36 g, 40.0 mol), THF (40 mL), and water (20 mL) was cooled to 0 °C. A solution of methyl 4-(chloromethacryl)benzoate in THF (20 mL) was added dropwise over 15 minutes, followed by warming to room temperature and vigorous stirring for 12 hours. After the reaction was complete, the solvent was concentrated under reduced pressure and extracted with ethyl acetate (50 mL × 3). The combined organic phases were washed with saturated sodium carbonate aqueous solution (50 mL) and saturated brine (50 mL), dehydrated with magnesium sulfate, and concentrated under reduced pressure to obtain a brown crude solid (crude yield: 23.5 g).

[0844] Methanol (50 mL) and 48% sodium hydroxide aqueous solution (2.5 mL, 45.2 mmol) were added to the crude solid, and the mixture was stirred at room temperature for 12 hours. After the reaction was complete, water (50 mL) was added, and the mixture was concentrated under reduced pressure. Concentrated hydrochloric acid was added to the residue to adjust the pH to 2, and the resulting solid was filtered off to obtain a white solid compound (2”A-1-47-CH) (yield: 3.65 g, total yield: 61%).

[0845] 1H-NMR (400MHz, DMSO-d6): δ13.04(brs,1H),9.45(s,1H),7.72(d,J=8.5Hz,2H),7.30(d,J=8.5Hz,2H),6.95(d,J=8.4Hz,1H) ,6.49(d,J=7.8Hz,1H),6.48(dd,J=7.8,2.7Hz,1H),3.99(dq,J=14.0,7.0Hz,1H),3.42(dq,J=14.0,7.0Hz,1H),2.03(s,3H).

[0846] [Synthesis Example 17]

[0847] [Chemical Engineering 202]

[0848] A mixture of 4-hydroxybenzoic acid (3.63 g, 26.3 mmol), thionyl chloride (24.60 g, 0.207 mol), and N,N-dimethylformamide (3.0 mg) was heated under reflux and stirred for 1 hour. The thionyl chloride was then distilled off to obtain 4-hydroxybenzoic acid chloride. The obtained 4-hydroxybenzoic acid chloride was used entirely as a THF (50 mL) solution in the next reaction.

[0849] Under nitrogen, a mixture of ethyl 4-(methylamino)benzoate (4.13 g, 25.0 mmol), water (50 mL), and THF (50 mL) was stirred while ice-cold, and sodium bicarbonate (4.20 g, 50.0 mmol) was added. Then, a pre-prepared THF solution of chloro 4-hydroxybenzoate was added dropwise over 5 minutes. After the addition, the mixture was slowly heated to room temperature while stirring for 12 hours, and then the THF was distilled off under reduced pressure. The resulting solid was filtered, washed with saturated sodium bicarbonate aqueous solution (50 mL) and water (50 mL), and dried under reduced pressure to obtain a white crude solid (crude yield: 7.12 g).

[0850] Methanol (85 mL) and 48% sodium hydroxide aqueous solution (2.8 mL, 50.0 mmol) were added to the crude solid, and the mixture was stirred at room temperature for 12 hours. After the reaction was complete, water (50 mL) was added, and the insoluble matter was separated by filtration. Concentrated hydrochloric acid was added to the filtrate to adjust the pH to 2, and the resulting solid was then filtered off to obtain a white solid compound (2”A-1-1-HC) (yield: 5.40 g, total yield: 80%).

[0851] 1H-NMR (400MHz, DMSO-d6): δ12.94(brs,1H),9.86(s,1H),7.81(d,J=8.6Hz,2H), 7.21(d,J=8.6Hz,2H),7.11(d,J=8.7Hz,2H),6.58(d,J=8.7Hz,2H),3.38(s,3H).

[0852] [Synthesis Example 18]

[0853]

[0854] A mixed solution of ethyl 4-(ethylamino)benzoate (13.6 g, 70.4 mmol), sodium bicarbonate (11.8 g, 0.14 mol), THF (85 mL), and water (170 mL) was cooled to 0 °C. A solution of 4-methoxybenzoic acid chloride (12.0 g, 70.3 mmol) in THF (85 mL) was added dropwise over 30 minutes. The mixture was then heated to room temperature and stirred vigorously for 12 hours. After the reaction was complete, the solvent was concentrated under reduced pressure and extracted with ethyl acetate (50 mL × 3). The combined organic phases were washed with saturated sodium carbonate aqueous solution (50 mL) and saturated brine (50 mL), dehydrated with magnesium sulfate, and concentrated under reduced pressure to obtain a brown crude solid (crude yield: 23.5 g).

[0855] The resulting crude solid solution in dichloromethane (30 mL) was cooled to 0 °C, and then a solution of boron tribromide (19.6 mL, 0.21 mmol) in dichloromethane (40 mL) was added dropwise over 30 minutes. The reaction system was heated to room temperature and stirred for 12 hours, then cooled back to 0 °C. 2 M hydrochloric acid (100 mL) was slowly added, and the mixture was concentrated under reduced pressure. After distilling off the solvent, the resulting solid was filtered off and washed with acetonitrile (50 mL). The solid was dried under reduced pressure. Meanwhile, the filtrate was extracted with ethyl acetate (100 mL × 3). The combined organic layers were dried over anhydrous magnesium sulfate and then concentrated under reduced pressure.

[0856] The residue was washed with cold acetonitrile (50 mL) and dried under reduced pressure to give a white solid compound (2”A-1-2-HC) (yield: 9.86 g, 49%).

[0857] 1H-NMR (400MHz, DMSO-d6): δ12.96(brs,1H),9.84(s,1H),7.81(d,J=8.7Hz,2H),7.18(d,J=8.7H z,2H),7.10(d,J=8.7Hz,2H),6.56(d,J=8.7Hz,2H),3.89(q,J=7.0Hz,2H),1.09(t,J=7.0Hz,3H).

[0858] [Synthesis Example 19]

[0859] [Chemical 204]

[0860] A mixed solution of methyl 3-methyl-4-(methylamino)benzoate (2.15 g, 12.0 mmol), triethylamine (3.03 mL, 23.9 mmol), and dichloromethane (40 mL) was cooled to 0 °C. A solution of 4-methoxybenzoic acid chloride (2.17 g, 12.6 mmol) in dichloromethane (15 mL) was added dropwise over 15 minutes, followed by warming to room temperature and stirring for 8 hours. After the reaction was complete, water (20 mL) was added, and the mixture was extracted with chloroform (50 mL × 3). The combined organic layers were dehydrated with magnesium sulfate and concentrated under reduced pressure to give a white crude solid (crude yield: 3.02 g).

[0861] The resulting crude solid solution in dichloromethane (30 mL) was cooled to 0 °C, and a solution of boron tribromide in dichloromethane (3.50 mL, 6.4 mmol) was added dropwise over 15 minutes. The reaction system was heated to room temperature and stirred for 12 hours, then cooled to 0 °C again. 2 M hydrochloric acid (10 mL) was slowly added, and the mixture was concentrated under reduced pressure. After distilling off the solvent, the resulting solid was filtered off and washed with acetonitrile (50 mL). The solid was dried under reduced pressure to give a white solid compound (2”A-1-46-HC) (yield: 2.34 g, total yield: 69%).

[0862] 1H-NMR (400MHz, DMSO-d6): δ12.98(brs,1H),9.81(s,1H),7.77(s,1H),7.69(d,J=7.1Hz,1H), 7.26(d,J=7.1Hz,1H),7.67(d,J=7.3Hz,2H),6.54(d,J=7.3Hz,2H),3.22(s,3H),2.17(s,3H).

[0863] [Example 1]

[0864] [Chemical Engineering 205]

[0865] Under a nitrogen stream, the compound (2”A-1-36-DH) (333 mg, 1.20 mmol) obtained as a diol monomer in Synthesis Example 1, and the compound (1'-2-1) (197 mg, 0.800 mmol) obtained as a dihydroxy compound in Example 1 were added to the reaction vessel. Then, a solution of sodium hydroxide (160 mg, 4.00 mmol) in water (19.2 mL) and a 2 wt% tetrabutylammonium bromide aqueous solution (0.8 mL) were added, and stirring was initiated. Further, trans-1,4-cyclohexanedicarboxylic acid dichloro (418 mg, 2.00 mmol), as a dicarboxylic acid dichloro monomer, was dissolved in chloroform (20 mL), and this solution was added to the reaction system. After stirring the reaction system for 3 hours, the mixture in the system was added to methanol (300 mL). The resulting solid was filtered off, washed with methanol (100 mL) and water (100 mL), and dried under vacuum to obtain 583 mg of polymer 1 (yield: 73%).

[0866] [Example 1-1]

[0867] 6.0% by mass of polymer 1 was dissolved in 94.0% by mass of 1,1,1,3,3,3-hexafluoroisopropanol. This solution was cast onto a quartz glass substrate, spin-coated, and dried in an oven at 60°C for 30 minutes to obtain a thin film. The resulting thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150°C. The phase difference and wavelength dispersion are shown in Table 1.

[0868] [Example 2]

[0869] [Chemical Engineering 206]

[0870] Except for the compound (2”A-1-36-DH) (222 mg, 0.800 mmol) obtained as a diol monomer in Example 1 and the compound (1'-2-1) (296 mg, 1.20 mmol) obtained as a dihydroxy compound in Example 1, 407 mg of polymer 2 (yield: 52%) was obtained by the same method as in Example 1.

[0871] [Example 2-1]

[0872] Using polymer 2 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0873] [Example 2-2]

[0874] Using polymer 2 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0875] [Examples 2-3]

[0876] Using polymer 2 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0877] [Examples 2-4]

[0878] Using polymer 2 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0879] [Example 3]

[0880]

[0881] Except for the compound (2”A-1-36-DH) (111 mg, 0.400 mmol) obtained as a diol monomer in Example 1 and the compound (1'-2-1) (394 mg, 1.60 mmol) obtained as a dihydroxy compound in Example 1, 527 mg of polymer 3 (yield: 68%) was obtained by the same method as in Example 1.

[0882] [Example 3-1]

[0883] Using polymer 3 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0884] [Example 3-2]

[0885] Using polymer 3 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0886] [Example 4]

[0887]

[0888] Except for the compounds (2”A-1-36-DH) (333 mg, 1.20 mmol) obtained as diol monomers in Synthesis Example 1, (1'-2-1) (98.4 mg, 0.400 mmol) and (6'-1-DH) (99.2 mg, 0.400 mmol) obtained in Dihydroxy Compound Example 1, 191 mg of polymer 4 (yield: 24%) was obtained by the same method as in Example 1.

[0889] [Example 4-1]

[0890] Using polymer 4 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0891] [Example 4-2]

[0892] Using polymer 4 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0893] [Example 4-3]

[0894] Using polymer 4 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0895] [Example 4-4]

[0896] Using polymer 4 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0897] [Example 5]

[0898]

[0899] Except for the compounds (2”A-1-1-DH) (292 mg, 1.20 mmol) obtained as diol monomers in Synthesis Example 2, (1'-2-1) (98.4 mg, 0.400 mmol) and (6'-1-DH) (99.2 mg, 0.400 mmol) obtained in Dihydroxy Compound Example 1, 191 mg of polymer 5 (yield: 42%) was obtained by the same method as in Example 1.

[0900] [Example 5-1]

[0901] Using polymer 5 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0902] [Example 5-2]

[0903] Using polymer 5 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0904] [Example 5-3]

[0905] Using polymer 5 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0906] [Example 5-4]

[0907] Using polymer 5 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0908] [Example 6]

[0909] [Chemical 210]

[0910] Except for the compounds (2”A-1-1-DH) (292 mg, 1.20 mmol) obtained as diol monomers in Synthesis Example 2, (1'-2-1) (98.4 mg, 0.400 mmol) obtained in Dihydroxy Compound Example 1, and (6'-2-DH) (126 mg, 0.400 mmol) obtained in Synthesis Example 6, 562 mg of polymer 6 (yield: 71%) was obtained by the same method as in Example 1.

[0911] [Example 6-1]

[0912] Using polymer 6 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0913] [Example 6-2]

[0914] Using polymer 6 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0915] [Example 6-3]

[0916] Using polymer 6 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0917] [Example 6-4]

[0918] Using polymer 6 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0919] [Example 7]

[0920]

[0921] Except for the compounds (2”A-1-1-DH) (292 mg, 1.20 mmol) obtained as diol monomers in Synthesis Example 2, (1'-2-1) (98.4 mg, 0.400 mmol) obtained in Dihydroxy Compound Example 1, and (6'-3-DH) (137 mg, 0.400 mmol) obtained in Synthesis Example 7, 457 mg of polymer 7 (yield: 57%) was obtained by the same method as in Example 1.

[0922] [Example 7-1]

[0923] Using polymer 7 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0924] [Example 7-2]

[0925] Using polymer 7 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0926] [Example 7-3]

[0927] Using polymer 7 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0928] [Example 7-4]

[0929] Using polymer 7 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0930] [Example 8]

[0931]

[0932] Except for the compounds (2”A-1-1-DH) (292 mg, 1.20 mmol) obtained as diol monomers in Synthesis Example 2, (1'-2-1) (98.4 mg, 0.400 mmol) obtained in Dihydroxy Compound Example 1, and (6'-5-DH) (118 mg, 0.400 mmol) obtained in Synthesis Example 8, 340 mg of polymer 8 (yield: 44%) was obtained by the same method as in Example 1.

[0933] [Example 8-1]

[0934] Using polymer 8 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0935] [Example 8-2]

[0936] Using polymer 8 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0937] [Example 8-3]

[0938] Using polymer 8 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0939] [Example 8-4]

[0940] Using polymer 8 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0941] [Example 9]

[0942] [Chemistry 213]

[0943] Except for the compounds (2”A-1-1-DH) (292 mg, 1.20 mmol) obtained as diol monomers in Synthesis Example 2, (1'-2-1) (98.4 mg, 0.400 mmol) obtained as dihydroxy compounds in Example 1, and (6'-7-DH) (119 mg, 0.400 mmol) obtained in Synthesis Example 9, 531 mg of polymer 9 (yield: 68%) was obtained by the same method as in Example 1.

[0944] [Example 9-1]

[0945] Using polymer 9 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0946] [Example 9-2]

[0947] Using polymer 9 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0948] [Example 9-3]

[0949] Using polymer 9 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0950] [Example 9-4]

[0951] Using polymer 9 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0952] [Example 10]

[0953]

[0954] Except for the compound (2”A-1-1-DH) (292 mg, 1.20 mmol) obtained as a diol monomer in Synthesis Example 2, the compound (1'-2-1) (98.4 mg, 0.400 mmol) obtained in Dihydroxy Compound Example 1, and the compound (6'-6-DH) (113 mg, 0.400 mmol) obtained in Synthesis Example 10, 658 mg of polymer 10 (yield: 85%) was obtained by the same method as in Example 1.

[0955] [Example 10-1]

[0956] Using polymer 10 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0957] [Example 10-2]

[0958] Using polymer 10 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0959] [Example 10-3]

[0960] Using polymer 10 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0961] [Example 11]

[0962]

[0963] Except for the compound (2”A-1-36-DH) (444 mg, 1.60 mmol) obtained as a diol monomer in Example 1 and the compound (1'-2-2) (112 mg, 0.400 mmol) obtained as a dihydroxy compound in Example 2, 354 mg of polymer 11 (yield: 43%) was obtained by the same method as in Example 1.

[0964] [Example 11-1]

[0965] Using polymer 11 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0966] [Example 11-2]

[0967] Using polymer 11 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0968] [Example 12]

[0969]

[0970] Except for the compound (2”A-1-36-DH) (333 mg, 1.60 mmol) obtained as a diol monomer in Example 1 and the compound (1'-2-2) (224 mg, 0.800 mmol) obtained as a dihydroxy compound in Example 2, 565 mg of polymer 12 (yield: 68%) was obtained by the same method as in Example 1.

[0971] [Example 12-1]

[0972] Using polymer 12 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0973] [Example 12-2]

[0974] Using polymer 12 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0975] [Examples 12-3]

[0976] Using polymer 12 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 313 nm polarized ultraviolet light at a intensity of 170 mJ / cm² and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0977] [Examples 12-4]

[0978] Using polymer 12 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 313 nm polarized ultraviolet light at a intensity of 170 mJ / cm² and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0979] [Examples 12-5]

[0980] Using polymer 12 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 340 mJ / cm² of polarized ultraviolet light at 313 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0981] [Examples 12-6]

[0982] Using polymer 12 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 700 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0983] [Examples 12-7]

[0984] Using polymer 12 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 365 nm polarized ultraviolet light at a intensity of 1400 mJ / cm² and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0985] [Example 13]

[0986]

[0987] Except for the compound (2”A-1-36-DH) (222 mg, 0.800 mmol) obtained as a diol monomer in Example 1 and the compound (1'-2-2) (337 mg, 1.20 mmol) obtained as a dihydroxy compound in Example 2, 463 mg of polymer 13 (yield: 56%) was obtained by the same method as in Example 1.

[0988] [Example 13-1]

[0989] Using polymer 13 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 50 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0990] [Example 13-2]

[0991] Using polymer 13 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 50 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0992] [Example 13-3]

[0993] Using polymer 13 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0994] [Examples 13-4]

[0995] Using polymer 13 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0996] [Examples 13-5]

[0997] Using polymer 13 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[0998] [Examples 13-6]

[0999] Using polymer 13 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[1000] [Examples 13-7]

[1001] Using polymer 13 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[1002] [Examples 13-8]

[1003] Using polymer 13 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 1.

[1004] [Examples 13-9]

[1005] Using polymer 13 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[1006] [Examples 13-10]

[1007] Using polymer 13 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 1.

[1008] [Example 14]

[1009]

[1010] Except for the compound (2”A-1-36-DH) (111 mg, 0.400 mmol) obtained as a diol monomer in Example 1 and the compound (1'-2-2) (449 mg, 1.60 mmol) obtained as a dihydroxy compound in Example 2, 595 mg of polymer 14 (yield: 72%) was obtained by the same method as in Example 1.

[1011] [Example 14-1]

[1012] Using polymer 14 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1013] [Example 14-2]

[1014] Using polymer 14 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1015] [Example 14-3]

[1016] Using polymer 14 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1017] [Example 14-4]

[1018] Using polymer 14 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1019] [Example 15]

[1020] [Chemistry 219]

[1021] Except for the compound (2”A-1-6-DH) (219 mg, 0.800 mmol) obtained as a diol monomer in Example 3 and the compound (1'-2-2) (337 mg, 1.20 mmol) obtained as a dihydroxy compound in Example 2, 343 mg of polymer 15 (yield: 41%) was obtained by the same method as in Example 1.

[1022] [Example 15-1]

[1023] Using polymer 15 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1024] [Example 15-2]

[1025] Using polymer 15 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1026] [Example 15-3]

[1027] Using polymer 15 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1028] [Example 15-4]

[1029] Using polymer 15 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1030] [Example 16]

[1031]

[1032] Under a nitrogen flow, in a reaction vessel, the following compounds were added: (2”A-1-1-DH) (212 mg, 0.871 mmol) obtained in Synthesis Example 2 as diol monomers; (1'-2-2) (571 mg, 2.03 mmol) obtained in Example 2 as dihydroxy compounds; and trans-1,4-cyclohexanedicarboxylic acid (400 mg, 2.32 mmol) and compound (2”-2-1-DC) (251 mg, 0.581 mmol) as dicarboxylic acid monomers. Then, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.23 g, 6.39 mmol) as a condensing agent, NMP (11.2 mL) as a solvent, and 4-dimethylaminopyridine (78.1 mg, 0.639 mmol) as a catalyst. Stirring was initiated. After stirring the reaction system for 3 hours, the mixture was added to methanol (300 mL). The solid produced was filtered out, washed with methanol (100 mL) and water (100 mL), and then dried under vacuum to obtain 455 mg of polymer 16 (yield: 34%).

[1033] [Example 16-1]

[1034] Using polymer 16 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1035] [Example 16-2]

[1036] Using polymer 16 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1037] [Example 16-3]

[1038] Using polymer 16 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1039] [Example 16-4]

[1040] Using polymer 16 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1041] [Example 17]

[1042] [Chemistry 221]

[1043] Except for the compound (2”A-1-2-DH) (299 mg, 1.16 mmol) obtained as a diol monomer in Synthesis Example 4, the compound (1'-2-2) (489 mg, 1.74 mmol) obtained as a dihydroxy compound in Example 2, and trans-1,4-cyclohexanedicarboxylic acid (500 mg, 2.90 mmol) as a dicarboxylic acid monomer, 511 mg of polymer 17 (yield: 43%) was obtained by the same method as in Example 16.

[1044] [Example 17-1]

[1045] Using polymer 17 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1046] [Example 17-2]

[1047] Using polymer 17 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1048] [Example 17-3]

[1049] Using polymer 17 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1050] [Example 17-4]

[1051] Using polymer 17 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1052] [Example 18]

[1053]

[1054] Except for the compound (2”A-1-2-DH) (149 mg, 0.581 mmol) obtained as a diol monomer in Synthesis Example 4, the compound (1'-2-2) (652 mg, 2.32 mmol) obtained as a dihydroxy compound in Example 2, trans-1,4-cyclohexanedicarboxylic acid (500 mg, 2.90 mmol) as a dicarboxylic acid monomer, and NMP (5.2 mL) as a solvent, 987 mg of polymer 18 (yield: 83%) was obtained by the same method as in Example 16.

[1055] [Example 18-1]

[1056] Using polymer 18 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1057] [Example 18-2]

[1058] Using polymer 18 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The resulting thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1059] [Example 19]

[1060]

[1061] Except for the compound (2”A-1-1-DH) (141 mg, 581 mmol) obtained as a diol monomer in Synthesis Example 2, the compound (1'-2-2) (652 mg, 2.32 mmol) obtained as a dihydroxy compound in Example 2, trans-1,4-cyclohexanedicarboxylic acid (500 mg, 2.90 mmol) as a dicarboxylic acid monomer, and NMP (29 mL) as a solvent, 414 mg of polymer 19 (yield: 35%) was obtained by the same method as in Example 16.

[1062] [Example 19-1]

[1063] Using polymer 19 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 50 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1064] [Example 19-2]

[1065] Using polymer 19 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1066] [Example 19-3]

[1067] Using polymer 19 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 50 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1068] [Example 19-4]

[1069] Using polymer 19 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1070] [Example 20]

[1071]

[1072] Except for the compound (2”A-1-1-DH) (195 mg, 0.800 mmol) obtained as a diol monomer in Synthesis Example 2, the compound (1'-2-1) (197 mg, 0.800 mmol) obtained in Dihydroxy Compound Example 1, and the compound (6'-5-DH) (118 mg, 0.400 mmol) obtained in Synthesis Example 8, 510 mg of polymer 20 (yield: 65%) was obtained by the same method as in Example 1.

[1073] [Example 20-1]

[1074] Using polymer 20 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The resulting thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1075] [Example 20-2]

[1076] Using polymer 20 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1077] [Example 21]

[1078]

[1079] Except for the compound (2”A-1-36-DH) (333 mg, 1.20 mmol) obtained as a diol monomer in Example 1 and the compound (1'-2-3) (260 mg, 0.800 mmol) obtained in Example 3 as a dihydroxy compound, 588 mg of polymer 21 (yield: 68%) was obtained by the same method as in Example 1.

[1080] [Example 21-1]

[1081] Using polymer 21 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1082] [Example 22]

[1083]

[1084] Except for the compound (2”A-1-36-DH) (222 mg, 0.800 mmol) obtained as a diol monomer in Example 1 and the compound (1'-2-3) (390 mg, 1.20 mmol) obtained in Example 3 as a dihydroxy compound, 621 mg of polymer 22 (yield: 70%) was obtained by the same method as in Example 1.

[1085] [Example 22-1]

[1086] Using polymer 22 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1087] [Example 22-2]

[1088] Using polymer 22 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1089] [Examples 22-3]

[1090] Using polymer 22 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1091] [Examples 22-4]

[1092] Using polymer 22 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1093] [Examples 22-5]

[1094] Using polymer 22 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1095] [Examples 22-6]

[1096] Using polymer 22 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1097] [Example 23]

[1098] [Chemistry 227]

[1099] Except for the compound (2”A-1-36-DH) (222 mg, 0.800 mmol) obtained as a diol monomer in Example 1 and the compound (1'-2-5) (331 mg, 1.20 mmol) obtained in Example 4 as a dihydroxy compound, 523 mg of polymer 23 (yield: 63%) was obtained by the same method as in Example 1.

[1100] [Example 23-1]

[1101] Using polymer 23 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1102] [Example 23-2]

[1103] Using polymer 23 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1104] [Example 23-3]

[1105] Using polymer 23 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1106] [Examples 23-4]

[1107] Using polymer 23 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1108] [Example 24]

[1109]

[1110] Except for the compound (2”A-1-36-DH) (333 mg, 1.20 mmol) obtained as a diol monomer in Example 1 and the compound (1'-2-5) (221 mg, 0.800 mmol) obtained in Example 4 as a dihydroxy compound, 690 mg of polymer 24 (yield: 84%) was obtained by the same method as in Example 1.

[1111] [Example 24-1]

[1112] Using polymer 24 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1113] [Example 24-2]

[1114] Using polymer 24 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1115] [Example 24-3]

[1116] Using polymer 24 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1117] [Example 24-4]

[1118] Using polymer 24 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1119] [Example 25]

[1120]

[1121] Except for the compound (2”A-1-1-DH) (292 mg, 1.20 mmol) obtained as a diol monomer in Example 2 and the compound (1'-2-5) (221 mg, 0.800 mmol) obtained in Example 4 as a dihydroxy compound, 512 mg of polymer 25 (yield: 65%) was obtained by the same method as in Example 1.

[1122] [Example 25-1]

[1123] Using polymer 25 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1124] [Example 25-2]

[1125] Using polymer 25 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1126] [Example 25-3]

[1127] Using polymer 25 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1128] [Example 25-4]

[1129] Using polymer 25 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1130] [Example 26]

[1131] [Chemistry 230]

[1132] Except for the compound (2”A-1-36-DH) (222 mg, 0.800 mmol) obtained as a diol monomer in Example 1 and the compound (1'-2-6) (312 mg, 1.20 mmol) obtained in Example 5 as a dihydroxy compound, 523 mg of polymer 26 (yield: 65%) was obtained by the same method as in Example 1.

[1133] [Example 26-1]

[1134] Using polymer 26 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1135] [Example 26-2]

[1136] Using polymer 26 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1137] [Example 27]

[1138] [Chemistry 231]

[1139] Except for the compound (2”A-1-36-DH) (333 mg, 1.20 mmol) obtained as a diol monomer in Example 1 and the compound (1'-2-6-Furan) (195 mg, 0.800 mmol) obtained in Example 6 as a dihydroxy compound, 445 mg of polymer 27 (yield: 56%) was obtained by the same method as in Example 1.

[1140] [Example 27-1]

[1141] Using polymer 27 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1142] [Example 27-2]

[1143] Using polymer 27 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 1000 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 2.

[1144] [Example 28]

[1145] [Chemistry 232]

[1146] Under a nitrogen atmosphere, in a reaction vessel, compound (2”D-1─1) (281 mg, 2.03 mmol) as a diol monomer, compound (1'-2-2) (1.06 g, 3.78 mmol) obtained in Example 2 of the dihydroxy compound, and trans-1,4-cyclohexanedicarboxylic acid (400 mg, 2.32 mmol) as a dicarboxylic acid monomer were added, followed by pyridine (7.9 mL) as a solvent. The mixture was heated to 30 °C and stirred. Diisopropylcarbodiimide (1.61 g, 12.8 mmol) as a condensing agent was then added. After stirring the reaction system for 3 hours, the mixture was added to methanol (300 mL). The resulting solid was filtered off, washed with methanol (500 mL) and water (300 mL), and dried under vacuum to obtain 1.56 g of polymer 28 (yield: 73%).

[1147] [Example 28-1]

[1148] Using polymer 28 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 3.

[1149] [Example 28-2]

[1150] Using polymer 28 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 190 °C. The phase difference and wavelength dispersion are shown in Table 3.

[1151] [Example 29]

[1152]

[1153] Except for the use of compound (2”B-1) (230 mg, 1.16 mmol) as a diol monomer, compound (1'-2-2) (489 mg, 1.74 mmol) obtained in Example 2 of dihydroxy compound, trans-1,4-cyclohexanedicarboxylic acid (500 mg, 2.90 mmol) as a dicarboxylic acid monomer, diisopropylcarbodiimide (806 mg, 6.39 mmol) as a condensing agent, and pyridine (4.2 mL) as a solvent, 606 mg of polymer 29 (yield: 54%) was obtained by the same method as in Example 28.

[1154] [Example 29-1]

[1155] Using polymer 29 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 3.

[1156] [Example 29-2]

[1157] Using polymer 29 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 190 °C. The phase difference and wavelength dispersion are shown in Table 3.

[1158] [Example 30]

[1159]

[1160] Except for the use of compound (2”B-1) (57.6 mg, 0.290 mmol) as a diol monomer, compound (1'-2-2) (489 mg, 1.74 mmol) obtained in Example 2 of dihydroxy compound, compound (2”A-1-1-DH) (212 mg, 0.871 mmol) obtained in Synthetic Example 2, trans-1,4-cyclohexanedicarboxylic acid (500 mg, 2.90 mmol) as a dicarboxylic acid monomer, diisopropylcarbodiimide (806 mg, 6.39 mmol) as a condensing agent, and pyridine (4.3 mL) as a solvent, 837 mg of polymer 30 (yield: 73%) was obtained by the same method as in Example 28.

[1161] [Example 30-1]

[1162] Using polymer 30 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 3.

[1163] [Example 30-2]

[1164] Using polymer 30 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 190 °C. The phase difference and wavelength dispersion are shown in Table 3.

[1165] [Example 31]

[1166]

[1167] Except for the compound (2”-1-1-DH) (1.44 g, 5.92 mmol) obtained as a diol monomer in Synthesis Example 2, the compound (1'-2-2) (3.22 g, 11.5 mmol) obtained as a dihydroxy compound in Example 2, PEG20000 (801 mg), trans-1,4-cyclohexanedicarboxylic acid (3.00 g, 17.4 mmol) as a dicarboxylic acid monomer, diisopropylcarbodiimide (4.84 g, 38.3 mmol) as a condensing agent, and pyridine (29.6 mL) as a solvent, 4.53 g of polymer 31 (yield: 58%) was obtained by the same method as in Example 28.

[1168] [Example 31-1]

[1169] Using polymer 31 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 3.

[1170] [Example 31-2]

[1171] Using polymer 31 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 190 °C. The phase difference and wavelength dispersion are shown in Table 3.

[1172] [Example 32]

[1173]

[1174] Except for the use of compound (2”B-1) (230 mg, 1.16 mmol) as a diol monomer, compound (2”D-1-1) (225 mg, 1.63 mmol), compound (1’-2-2) (848 mg, 3.02 mmol) obtained in Example 2 as a dihydroxy compound, trans-1,4-cyclohexanedicarboxylic acid (1.00 g, 5.81 mmol) as a dicarboxylic acid monomer, diisopropylcarbodiimide (1.61 g, 12.8 mmol) as a condensing agent, and pyridine (16.2 mL) as a solvent, 1.36 g of polymer 32 (yield: 65%) was obtained by the same method as in Example 28.

[1175] [Example 32-1]

[1176] Using polymer 32 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 3.

[1177] [Example 32-2]

[1178] Using polymer 32 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 190 °C. The phase difference and wavelength dispersion are shown in Table 3.

[1179] [Example 33]

[1180]

[1181] Except for the use of compound (2”C-1-6) (833 mg, 2.32 mmol) as a diol monomer, compound (1'-2-2) (978 mg, 3.49 mmol) obtained in Example 2 of dihydroxy compound, trans-1,4-cyclohexanedicarboxylic acid (1.00 mg, 5.81 mmol) as a dicarboxylic acid monomer, diisopropylcarbodiimide (1.61 g, 12.8 mmol) as a condensing agent, and pyridine (9.8 mL) as a solvent, 2.02 g of polymer 33 (yield: 78%) was obtained by the same method as in Example 28.

[1182] [Example 33-1]

[1183] Using polymer 33 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 190 °C. The phase difference and wavelength dispersion are shown in Table 3.

[1184] [Example 34]

[1185]

[1186] Except for the dihydroxy compound (1'-2-2) (1.40 g, 5.00 mmol) obtained in Example 2 as the diol monomer, trans-1,4-cyclohexanedicarboxylic acid (861 mg, 5.00 mmol) as the dicarboxylic acid monomer, diisopropylcarbodiimide (1.39 g, 11.0 mmol) as the condensing agent, pyridine (2.0 mL) and NMP (1.9 mL) as the solvent, 1.77 g of polymer 34 (yield: 85%) was obtained by the same method as in Example 28.

[1187] [Example 34-1]

[1188] Using polymer 34 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 3.

[1189] [Example 35]

[1190] [Chemistry 239]

[1191] Except for the compound (2”A-1-1-DH) (212 mg, 0.871 mmol) obtained as a diol monomer in Synthesis Example 2, the compound (1’-2-2) (489 mg, 1.74 mmol) obtained as a dihydroxy compound in Example 2, methylhydroquinone (2”D-5-1) (36.0 mg, 0.290 mmol), trans-1,4-cyclohexanedicarboxylic acid (2”D-7-3) (500 mg, 2.90 mmol) as a dicarboxylic acid monomer, diisopropylcarbodiimide (806 mg, 6.39 mmol) as a condensing agent, and pyridine (4.2 mL) as a solvent, 884 mg of polymer 35 (yield: 76%) was obtained by the same method as in Example 28.

[1192] [Example 35-1]

[1193] Using polymer 35 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 190 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1194] [Example 36]

[1195] [Chemistry 240]

[1196] Except for the compound (2”A-1-1-DH) (212 mg, 0.871 mmol) obtained as a diol monomer in Synthesis Example 2, the compound (1’-2-2) (489 mg, 1.74 mmol) obtained as a dihydroxy compound in Example 2, chlorohydroquinone (2”D-6-1) (42.0 mg, 0.290 mmol), trans-1,4-cyclohexanedicarboxylic acid (2”D-7-3) (500 mg, 2.90 mmol) as a dicarboxylic acid monomer, diisopropylcarbodiimide (806 mg, 6.39 mmol) as a condensing agent, and pyridine (4.2 mL) as a solvent, 889 mg of polymer 36 (yield: 78%) was obtained by the same method as in Example 28.

[1197] [Example 36-1]

[1198] Using polymer 36 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 190 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1199] [Example 37]

[1200] [Chemistry 241]

[1201] Except for the compound (2”A-1-1-DH) (212 mg, 0.871 mmol) obtained as a diol monomer in Synthesis Example 2, the compound (1’-2-2) (489 mg, 1.74 mmol) obtained as a dihydroxy compound in Example 2, the tert-butylhydroquinone (2”D-8-1) (48.3 mg, 0.290 mmol), trans-1,4-cyclohexanedicarboxylic acid (2”D-7-3) (500 mg, 2.90 mmol) as a dicarboxylic acid monomer, diisopropylcarbodiimide (806 mg, 6.39 mmol) as a condensing agent, and pyridine (4.3 mL) as a solvent, 872 mg of polymer 37 (yield: 76%) was obtained by the same method as in Example 28.

[1202] [Example 37-1]

[1203] Using polymer 37 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 190 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1204] [Example 38]

[1205] [Chemistry 242]

[1206] Except for the compound (2”A-1-1-DH) (212 mg, 0.871 mmol) obtained as a diol monomer in Synthesis Example 2, the compound (1’-2-2) (489 mg, 1.74 mmol) obtained as a dihydroxy compound in Example 2, 2,5-ditert-butylhydroquinone (2”D-11-1) (64.6 mg, 0.290 mmol), trans-1,4-cyclohexanedicarboxylic acid (2”D-7-3) (500 mg, 2.90 mmol) as a dicarboxylic acid monomer, diisopropylcarbodiimide (806 mg, 6.39 mmol) as a condensing agent, and pyridine (4.3 mL) as a solvent, 876 mg of polymer 38 (yield: 76%) was obtained by the same method as in Example 28.

[1207] [Example 38-1]

[1208] Using polymer 38 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 190 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1209] [Example 39]

[1210] [Chemistry 243]

[1211] Except for the compound (2”A-1-1-DH) (212 mg, 0.871 mmol) obtained as a diol monomer in Synthesis Example 2, the compound (1'-2-2) (489 mg, 1.74 mmol) obtained as a dihydroxy compound in Example 2, 6,6'-dihydroxy-4,4,4',4',7,7'-hexamethyl-2,2'-spirobenzyl dihydropyran (2”D-14-1) (107 mg, 0.290 mmol) as a dicarboxylic acid monomer, trans-1,4-cyclohexanedicarboxylic acid (2”D-7-3) (500 mg, 2.90 mmol) as a dicarboxylic acid monomer, diisopropylcarbodiimide (806 mg, 6.39 mmol) as a condensing agent, and pyridine (4.5 mL) as a solvent, 841 mg of polymer 39 (yield: 64%) was obtained by the same method as in Example 28.

[1212] [Example 39-1]

[1213] Using polymer 39 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 190 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1214] [Example 40]

[1215] [Chemistry 244]

[1216] Except for the dihydroxy compounds (1'-2-2) (847 mg, 3.02 mmol) obtained in Example 2 as diol monomers, compound (2”D-1-1) (192 mg, 1.39 mmol), 2-(1,1,3,3-tetramethylbutyl)hydroquinone (2”D-10-1) (310 mg, 1.39 mmol), PEG20000 (116 mg, 5.81 μmol), trans-1,4-cyclohexanedicarboxylic acid (2”D-7-3) (1.00 g, 5.81 mmol) as dicarboxylic acid monomer, diisopropylcarbodiimide (1.61 g, 12.8 mmol) as condensing agent, and pyridine (8.4 mL) as solvent, 1.33 g of polymer 40 (yield: 59%) was obtained by the same method as in Example 28.

[1217] [Example 40-1]

[1218] Using polymer 40 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1219] [Example 41]

[1220] [Chemistry 245]

[1221] Except for the dihydroxy compounds (1'-2-2) (1.04 g, 3.72 mmol) obtained in Example 2 as diol monomers, compound (2”D-1-1) (225 mg, 1.63 mmol), compound (2”C-2-2) (133 mg, 465 μmol) obtained in Synthesis Example 11, trans-1,4-cyclohexanedicarboxylic acid (2”D-7-3) (1.00 g, 5.81 mmol) as dicarboxylic acid monomer, diisopropylcarbodiimide (1.61 g, 12.8 mmol) as condensing agent, and pyridine (8.1 mL) as solvent, 1.71 g of polymer 41 (yield: 78%) was obtained by the same method as in Example 28.

[1222] [Example 41-1]

[1223] Using polymer 41 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1224] [Example 42]

[1225] [Chemistry 246]

[1226] Except for the dihydroxy compound (1'-2-2) (1.24 g, 4.43 mmol) obtained in Example 2 as a diol monomer, the compound (2”A-1-104-DH) (541 mg, 1.36 mmol) obtained in Synthesis Example 12, PEG20000 (263 mg, 13.1 μmol), trans-1,4-cyclohexanedicarboxylic acid (2”D-7-3) (1.00 g, 5.81 mmol) as a dicarboxylic acid monomer, diisopropylcarbodiimide (1.61 g, 12.8 mmol) as a condensing agent, and pyridine (10.8 mL) as a solvent, 1.80 g of polymer 42 (yield: 63%) was obtained by the same method as in Example 28.

[1227] [Example 42-1]

[1228] Using polymer 42 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1229] [Example 43]

[1230] [Chemistry 247]

[1231] Except for the use of the dihydroxy compound (1'-2-2) (1.06 g, 3.78 mmol) obtained in Example 2 as a diol monomer, the compound (2”A-1-1-CH) (879 mg, 3.24 mmol) obtained in Synthesis Example 13 as a hydroxycarboxylic acid monomer, the trans-1,4-cyclohexanedicarboxylic acid (2”D-7-3) (651 mg, 3.78 mmol) as a dicarboxylic acid monomer, the diisopropylcarbodiimide (1.50 g, 11.9 mmol) as a condensing agent, and the pyridine (9.1 mL) as a solvent, 1.47 g of polymer 43 (yield: 61%) was obtained by the same method as in Example 28.

[1232] [Example 43-1]

[1233] Using polymer 43 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 190 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1234] [Example 44]

[1235] [Chemistry 248]

[1236] Except for the dihydroxy compound (1'-2-2) (1.06 mg, 3.78 mmol) obtained in Example 2 as a diol monomer, the compound (2”A-1-2-CH) (925 mg, 3.24 mmol) obtained in Synthesis Example 14 as a hydroxycarboxylic acid monomer, the trans-1,4-cyclohexanedicarboxylic acid (2”D-7-3) (651 mg, 3.78 mmol) as a dicarboxylic acid monomer, the diisopropylcarbodiimide (1.50 g, 11.9 mmol) as a condensing agent, and the pyridine (9.2 mL) as a solvent, 1.42 g of polymer 44 (yield: 58%) was obtained by the same method as in Example 28.

[1237] [Example 44-1]

[1238] Using polymer 44 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 190 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1239] [Example 45]

[1240] [Chemistry 249]

[1241] Except for the use of the dihydroxy compound (1'-2-2) (708 mg, 2.52 mmol) obtained in Example 2 as a diol monomer, the compound (2”A-1-46-CH) (617 mg, 2.16 mmol) obtained in Synthesis Example 15 as a hydroxycarboxylic acid monomer, the trans-1,4-cyclohexanedicarboxylic acid (2”D-7-3) (434 mg, 2.52 mmol) as a dicarboxylic acid monomer, the diisopropylcarbodiimide (1.00 g, 7.92 mmol) as a condensing agent, and the pyridine (6.1 mL) as a solvent, 1.02 g of polymer 45 (yield: 62%) was obtained by the same method as in Example 28.

[1242] [Example 45-1]

[1243] Using polymer 45 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 190 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1244] [Example 46]

[1245] [Chemistry 250]

[1246] The following compounds were obtained in Example 28: (1'-2-2) (708 mg, 2.52 mmol) as diol monomers, (2”A-1-47-CH) (647 mg, 2.16 mmol) as hydroxycarboxylic acid monomers, (2”D-7-3) (434 mg, 2.52 mmol) as dicarboxylic acid monomers, (1.00 g, 7.92 mmol) as condensing agent, and (6.3 mL) as solvent (diisopropylcarbodiimide). Polymer 46 (yield: 77%) was obtained in the same manner as in Example 28.

[1247] [Example 46-1]

[1248] Using polymer 46 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 190 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1249] [Example 46-2]

[1250] Using polymer 46 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1251] [Example 47]

[1252]

[1253] Except for the use of the dihydroxy compound (1'-2-2) (708 mg, 2.52 mmol) obtained in Example 2 as a diol monomer, the compound (2”A-1-1-HC) (586 mg, 2.16 mmol) obtained in Synthesis Example 17 as a hydroxycarboxylic acid monomer, the trans-1,4-cyclohexanedicarboxylic acid (2”D-7-3) (434 mg, 2.52 mmol) as a dicarboxylic acid monomer, the diisopropylcarbodiimide (1.00 g, 7.92 mmol) as a condensing agent, and the pyridine (6.0 mL) as a solvent, 979 mg of polymer 47 (yield: 61%) was obtained by the same method as in Example 28.

[1254] [Example 47-1]

[1255] Using polymer 47 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 190 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1256] [Example 48]

[1257] [Chemistry 252]

[1258] Except for the use of the dihydroxy compound (1'-2-2) (708 mg, 2.52 mmol) obtained in Example 2 as a diol monomer, the compound (2”A-1-2-HC) (616 mg, 2.16 mmol) obtained in Synthesis Example 18 as a hydroxycarboxylic acid monomer, the trans-1,4-cyclohexanedicarboxylic acid (2”D-7-3) (434 mg, 2.52 mmol) as a dicarboxylic acid monomer, the diisopropylcarbodiimide (1.00 g, 7.92 mmol) as a condensing agent, and the pyridine (6.2 mL) as a solvent, 1.03 g of polymer 48 (yield: 63%) was obtained by the same method as in Example 28.

[1259] [Example 48-1]

[1260] Using polymer 48 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 190 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1261] [Example 48-2]

[1262] Using polymer 48 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1263] [Example 49]

[1264]

[1265] Except for the use of the dihydroxy compound (1'-2-2) (708 mg, 2.52 mmol) obtained in Example 2 as a diol monomer, the compound (2”A-1-46-HC) (617 mg, 2.16 mmol) obtained in Synthesis Example 19 as a hydroxycarboxylic acid monomer, the trans-1,4-cyclohexanedicarboxylic acid (2”D-7-3) (434 mg, 2.52 mmol) as a dicarboxylic acid monomer, the diisopropylcarbodiimide (1.00 g, 7.92 mmol) as a condensing agent, and the pyridine (6.1 mL) as a solvent, 1.07 g of polymer 49 (yield: 66%) was obtained by the same method as in Example 28.

[1266] [Example 49-1]

[1267] Using polymer 49 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 190 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1268] [Example 49-2]

[1269] Using polymer 49 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 250 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1270] [Example 50]

[1271]

[1272] Except for the dihydroxy compound (1'-6-2) (424 mg, 1.74 mmol) obtained in Example 11 as a diol monomer, the compound (2”A-1-1-DH) (283 mg, 1.16 mmol) obtained in Synthetic Example 2, the trans-1,4-cyclohexanedicarboxylic acid (2”D-7-3) (500 mg, 2.90 mmol) as a dicarboxylic acid monomer, the diisopropylcarbodiimide (806 mg, 6.39 mmol) as a condensing agent, and the pyridine (4.1 mL) as a solvent, 738 mg of polymer 50 (yield: 67%) was obtained by the same method as in Example 28.

[1273] [Example 50-1]

[1274] Using polymer 50 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 190 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1275] [Example 51]

[1276] [Chemistry 255]

[1277] Except for the dihydroxy compound (1'-6-3) (448 mg, 1.74 mmol) obtained in Example 12 as a diol monomer, the compound (2”A-1-1-DH) (283 mg, 1.16 mmol) obtained in Synthetic Example 2, the trans-1,4-cyclohexanedicarboxylic acid (2”D-7-3) (500 mg, 2.90 mmol) as a dicarboxylic acid monomer, the diisopropylcarbodiimide (806 mg, 6.39 mmol) as a condensing agent, and the pyridine (4.1 mL) as a solvent, 657 mg of polymer 51 (yield: 58%) was obtained by the same method as in Example 28.

[1278] [Example 51-1]

[1279] Using polymer 51 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 150 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1280] [Example 52]

[1281] [Chemistry 256]

[1282] Except for the use of the dihydroxy compound (1'-2-10) (514 mg, 1.74 mmol) obtained in Example 8 as a diol monomer, the compound (2”A-1-1-DH) (283 mg, 1.16 mmol) obtained in Synthetic Example 2, the trans-1,4-cyclohexanedicarboxylic acid (2”D-7-3) (500 mg, 2.90 mmol) as a dicarboxylic acid monomer, the diisopropylcarbodiimide (806 mg, 6.39 mmol) as a condensing agent, and the pyridine (4.5 mL) as a solvent, 966 mg of polymer 52 (yield: 81%) was obtained by the same method as in Example 28.

[1283] [Example 52-1]

[1284] Using polymer 52 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 190 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1285] [Example 53]

[1286] [Chemistry 257]

[1287] Except for the use of compound (1'-2-9) (514 mg, 1.74 mmol) obtained in Example 7 as a diol monomer dihydroxy compound, compound (2”A-1-1-DH) (283 mg, 1.16 mmol) obtained in Synthetic Example 2, trans-1,4-cyclohexanedicarboxylic acid (2”D-7-3) (500 mg, 2.90 mmol) as a dicarboxylic acid monomer, diisopropylcarbodiimide (806 mg, 6.39 mmol) as a condensing agent, and pyridine (4.5 mL) as a solvent, 884 mg of polymer 53 (yield: 74%) was obtained by the same method as in Example 28.

[1288] [Example 53-1]

[1289] Using polymer 53 instead of polymer 1, a thin film was obtained in the same manner as in Examples 1-1. The obtained thin film (1 μm thick) was irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and then heated to 190 °C. The phase difference and wavelength dispersion are shown in Table 4.

[1290] [Example 54]

[1291] [Chemistry 258]

[1292] Except for the dihydroxy compound (1'-2-11) (157 mg, 499 μmol) obtained in Example 9 as a diol monomer, the compound (2”A-1-1-DH) (243 mg, 999 μmol) and the compound (2”D-1-1) (138 mg, 999 μmol) obtained in Synthetic Example 2 as a dihydroxy compound, the trans-1,4-cyclohexanedicarboxylic acid (2”D-7-3) (430 mg, 2.50 mmol) as a dicarboxylic acid monomer, the diisopropylcarbodiimide (693 mg, 5.49 mmol) as a condensing agent, and the pyridine (3.2 mL) as a solvent, 483 mg of polymer 54 (yield: 55%) was obtained by the same method as in Example 28.

[1293] [Example 55]

[1294] [Chemistry 259]

[1295] Except for the dihydroxy compound (1'-7-2) (225 mg, 499 μmol) obtained in Example 10 as a diol monomer, the compound (2”A-1-1-DH) (243 mg, 999 μmol) and the compound (2”D-1-1) (138 mg, 999 μmol) obtained in Synthetic Example 2, the trans-1,4-cyclohexanedicarboxylic acid (2”D-7-3) (430 mg, 2.50 mmol) as a dicarboxylic acid monomer, the diisopropylcarbodiimide (693 mg, 5.49 mmol) as a condensing agent, and the pyridine (3.5 mL) as a solvent, 699 mg of polymer 55 (yield: 74%) was obtained by the same method as in Example 28.

[1296] [Example 56]

[1297] [Chemistry 260]

[1298] Except for the dihydroxy compounds (1'-2-2) (946 mg, 3.37 mmol) obtained in Example 2 as diol monomers, compound (2”D-1-1) (233 mg, 1.68 mmol), 2-(1,1,3,3-tetramethylbutyl)hydroquinone (2”D-10-1) (214 mg, 963 mmol), PEG20000 (60.3 mg, 3.01 μmol), terephthalic acid (1.00 g, 1.68 mmol) as a dicarboxylic acid monomer, diisopropylcarbodiimide (693 mg, 5.49 mmol) as a condensing agent, and pyridine (3.5 mL) as a solvent, 1.21 g of polymer 56 (yield: 54%) was obtained by the same method as in Example 28.

[1299] [Comparative Example 1]

[1300]

[1301] In a 200 mL three-necked flask equipped with a dropping funnel, 20 mL of deionized water was added, along with 1.11 g (4.00 mmol) of the compound (2”-1-36-DH) obtained in Synthesis Example 1 and 320 mg (8.00 mmol) of sodium hydroxide. After the matrix was dissolved by vigorous stirring (350 rpm), 1.6 mL of a 2% tetrabutylammonium bromide aqueous solution was added as a catalyst, and the apparatus was thoroughly purged with argon. A 20 mL solution of dichloromethane containing trans-1,4-cyclohexanedicarboxylic acid dichloromethane was quickly added dropwise into the system via the dropping funnel. After the addition was complete, the mixture was vigorously stirred at room temperature for 3 hours to carry out interfacial polymerization. After the reaction, the solution was added dropwise to 200 mL of methanol. The precipitate was filtered and separated, washed with 100 mL of water and 100 mL of methanol, and dried under vacuum to obtain 1.04 g of a white solid polymer 1' (yield: 63%).

[1302] 6.0% by mass of polymer 1' was dissolved in 94.0% by mass of 1,1,1,3,3,3-hexafluoro-2-propanol. This solution was cast onto a quartz glass substrate, spin-coated, and dried in an oven at 60°C for 30 minutes to obtain a thin film (1 μm thick). The obtained film was irradiated with 500 mJ / cm² of polarized ultraviolet light at 248 nm and then heated to 250°C. The phase difference and wavelength dispersion are shown in Table 5.

[1303]

[1304]

[1305]

[1306]

[1307]

[1308] In Tables 1, 2, 3, 4, and 5, R(450) / R(550) represents the ratio of the in-plane phase difference at 450 nm to the in-plane phase difference at 550 nm.

[1309] Re[10μm] represents the value of the phase difference calculated based on a film thickness of 10μm.

[1310] As shown in Tables 1, 2, 3 and 4, the polymers of Examples 1 to 53 exhibited a phase difference with reverse wavelength dispersion after being irradiated with ultraviolet light and heated.

[1311] The polymers of the present invention, which have photoreactive reverse wavelength dispersion units A, exhibit a more significant phase difference in reverse wavelength dispersion compared to Comparative Example 1 as shown in Table 5.

[1312] [Dihydroxy compound Example 14]

[1313] 2,5-Dihydroxybenzaldehyde (57.5 g, 416 mmol) and acetophenone (50.0 g, 416 mmol) were dissolved in methanol (200 mL), and then 50% sodium hydroxide aqueous solution (120 mL, 2.25 mol) was added dropwise under ice-cold conditions. The reaction system was stirred at room temperature for 12 hours, and then acetic acid (167 mL, 2.91 mmol) was added under ice-cold conditions. The resulting reaction mixture was added to water (300 mL), followed by toluene (30 mL), isopropanol (2 mL), and dichloromethane (100 mL), and stirred vigorously. The resulting solid was filtered off and washed with dichloromethane (50 mL) and distilled water (50 mL). The solid was dried under vacuum to give 14.8 g of compound (1'-1-1) as a yellow solid (yield: 15%).

[1314] 1H-NMR(400MHz,DMSO-d6)δ9.90-8.39(br,2H),8.04(d,J=8.2Hz,2H),7.94(d,J=15.4Hz,1H),7.6 7(d,J=15.4Hz,1H),7.61(t,J=7.4Hz,1H),7.52(t,J=7.4Hz,2H),7.15(s,1H),6.76-6.67(m,2H).

[1315]

[1316] [Synthesis example 20-1]

[1317] Under argon atmosphere, a mixture of 4-acetylated benzoic acid (7.56 g, 42.0 mmol), thionyl chloride (24.0 mL, 331 mmol), and N,N-dimethylformamide (catalyst amount) was refluxed and boiled for 3 hours. The volatile components were distilled off, and 4-acetylated benzoic acid chloride was obtained by azeotropic reaction with toluene (3 × 20 mL). The obtained 4-acetylated benzoic acid chloride was used entirely as a tetrahydrofuran (50 mL) solution in the next reaction.

[1318] Under argon atmosphere, 1,2-dimethylhydrazine dihydrochloride (2.66 g, 20.0 mmol) and N,N-diisopropylethylamine (17.0 mL, 100 mmol) were suspended in tetrahydrofuran (40 mL). A pre-prepared solution of 4-acetoxybenzoic acid chloride in tetrahydrofuran was slowly added while ice-cold, and the mixture was heated to room temperature and stirred overnight. The solvent was distilled off under reduced pressure, and 1 M hydrochloric acid (100 mL) was added, followed by extraction with ethyl acetate (2 × 100 mL). The combined organic layers were washed sequentially with saturated sodium bicarbonate aqueous solution (100 mL) and saturated brine (100 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was suspended in methanol (75 mL), and a solution of sodium hydroxide (4.16 g, 104 mmol) in water (25 mL) was added, and the mixture was stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure, and 2M hydrochloric acid (75 mL) was added. Extraction was performed with ethyl acetate (2 × 100 mL). The combined organic layers were washed sequentially with saturated sodium bicarbonate aqueous solution (2 × 100 mL) and saturated brine (100 mL), and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography. The resulting solid was recrystallized from the solid by a mixed solvent of ethanol / hexane to give a white solid compound (2”C-2-13) (yield: 3.02 g, 50%).

[1319] 1H-NMR (400MHz, (CD3)2SO): δ9.95(brs,2H),7.58-6.87(brm,4H),6.87-6.61(brm,4H),3.13(brs,6H).

[1320]

[1321] [Example 57]

[1322] Under nitrogen conditions, the dihydroxy compound (1'-2-2) (4.0 g, 14.3 mmol) obtained in Example 2, the compound (2”A-1-1-DH) (1.9 g, 7.7 mmol) obtained in Synthesis Example 2, trans-1,4-cyclohexanedicarboxylic acid (3.8 g, 21.9 mmol), pyridine (8.2 mL), and N-methyl-2-pyrrolidone (8.2 mL) were added to a reaction vessel. After the reaction system was stirred at 40 °C for 1 hour to dissolve the compounds, N,N'-diisopropylcarbodiimide (6.1 g, 48.2 mmol) was added dropwise as an ester-bonding condensing agent to initiate polymerization. After stirring the reaction system at 40 °C for 3 hours, acetic anhydride (2.2 g, 21.9 mmol) was added as a monocarboxylic acid derivative. After stirring the reaction system at 40°C for 30 minutes, the mixture in the system was added to methanol (300 mL). The resulting solid was filtered out, washed with methanol (500 mL), and dried under vacuum to obtain polymer 57 (yield: 6.4 g, yield: 72%).

[1323]

[1324] 13.0% by mass of polymer 57 was dissolved in 87.0% by mass of hexafluoro-2-propanol. This solution was cast onto a quartz substrate, spin-coated at 2000 rpm for 60 seconds, and dried in an oven at 60°C for 30 minutes to obtain a film (5 μm thick). The film was evaluated by measuring its yellowness (YI) and visual appearance. The film was then irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and heated at 150°C for 10 minutes to evaluate its phase difference and wavelength dispersion characteristics. The results are shown in Table 6.

[1325] [Example 58]

[1326] Under nitrogen conditions, the following compounds were added to a reaction vessel: compound (1'-2-2) (4.0 g, 14.3 mmol) obtained in Example 2 (dihydroxy compound), compound (2”A-1-1-DH) (1.9 g, 7.7 mmol) obtained in Example 2 (synthetic compound), trans-1,4-cyclohexanedicarboxylic acid (3.8 g, 21.9 mmol), pyridine (8.2 mL), and N-methyl-2-pyrrolidone (8.2 mL). The reaction system was stirred at 40 °C for 1 hour to dissolve the compounds, and then the mixture was added dropwise as an ester-bonding condensation. The polymerization of N,N'-diisopropylcarbodiimide (6.1 g, 48.2 mmol) was initiated. After stirring the reaction system at 40 °C for 3 hours, cyclohexanecarbamate (3.2 g, 21.9 mmol) was added as a monocarboxylic acid derivative. The reaction system was stirred at 40 °C for 30 minutes, and the mixture was then added to methanol (300 mL). The resulting solid was filtered, washed with methanol (500 mL), and dried under vacuum to obtain polymer 58 (yield: 6.6 g, 75%).

[1327]

[1328] 13.0% by mass of polymer 58 was dissolved in 87.0% by mass of hexafluoro-2-propanol. This solution was cast onto a quartz substrate, spin-coated at 1600 rpm for 60 seconds, and dried in an oven at 60°C for 30 minutes to obtain a film (5 μm thick). The film was evaluated by measuring its yellowness (YI) and visual appearance. The film was then irradiated with 100 mJ / cm² of polarized ultraviolet light at 365 nm and heated at 150°C for 10 minutes to evaluate its phase difference and wavelength dispersion characteristics. The results are shown in Table 5.

[1329] [E...

Claims

1. A main-chain polymer having a photoreactive reverse wavelength dispersive unit within the polymer main chain that exhibits both photoreactivity and birefringence in reverse wavelength dispersibility, wherein the photoreactive reverse wavelength dispersive unit has the structure represented by the following chemical formula (1): [Chemical 1] [In the aforementioned chemical formula (1), L1 and L2 may be the same or different, representing carbonyl, ester, amide, ether, or single bond; * indicates the bonding position with other structures in the aforementioned main-chain polymer; Ar represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms are designated as the atoms constituting the ring, and these monocyclic aromatic rings, polycyclic aromatic rings, or condensed aromatic rings may have substituents; R0, R1, R2, R3, and R4 independently represent hydrogen atoms, halogen atoms, alkyl groups with 1 to 8 carbon atoms, or groups represented by the following chemical formula (Z1); [Chemical 2] [In the aforementioned chemical formula (Z1), Rz3 and Rz4 independently represent hydrogen atoms, halogen atoms, or alkyl groups with 1 to 8 carbon atoms; Arz represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are set as the atoms constituting the ring, and these monocyclic aromatic rings, polycyclic aromatic rings, or condensed aromatic rings may have substituents; the wavy part represents the bond position with the part other than R0, R1, R2, R3, or R4 in formula (1).

2. The main-chain polymer as described in claim 1, wherein, In the aforementioned chemical formula (1), Ar is any of the following chemical formulas (Ar-1) to (Ar-7): [Chemical 3] [In the aforementioned chemical formulas (Ar-1) to (Ar-7), X1, X2, X3, X4, X5, X6, X7, and X8 independently represent hydrogen atoms or alkyl groups with 1 to 8 carbon atoms, alkoxy groups with 1 to 6 carbon atoms, halogen atoms, nitro groups, cyano groups, alkylthio groups with 1 to 6 carbon atoms, or dialkylamino groups with 2 to 8 carbon atoms; Re represents hydrogen atoms or alkyl groups with 1 to 10 carbon atoms; ** represents the bonding position with the other parts in the aforementioned chemical formula (1) except Ar].

3. The main-chain polymer as claimed in claim 1 further comprises: at least one structure selected from the group consisting of the following chemical formulas (2A), (2B), (2C) and (2D): [Chemical 4] [In the aforementioned chemical formula (2A), ring C, ring D and ring E independently represent a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings and aliphatic hydrocarbon rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms and sulfur atoms are set as atoms constituting the ring, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings and aliphatic hydrocarbon rings may have substituents; R5 and R6 may be the same or different, representing a group selected from the group consisting of hydrogen atoms, alkyl groups with 1 to 20 substituted carbon atoms, cycloalkyl groups with 3 to 8 substituted carbon atoms, and aromatic groups with 3 to 12 substituted carbon atoms; n is 0 or 1;] L3 and L4 may be the same or different, representing carbonyl, ester, amide, ether, or single bond; *** indicates the bond position with other structures in the aforementioned main-chain polymer]; [Chemistry 5] [In the aforementioned chemical formula (2B), L9 and L10 may be the same or different, representing carbonyl, ester, amide, ether, or single bond; *** indicates the bond position with other structures in the aforementioned main-chain polymer]; [Chemistry 6] [In the aforementioned chemical formula (2C), X9 represents an alkyl chain with 1 to 10 carbon atoms, or a single bond; X10 represents -O-, -N(Rc)-; X11 represents -O-, -N(Rd)-; Rc and Rd may be the same or different, representing hydrogen atoms or alkyl groups with 1 to 10 carbon atoms; L11 and L12 may be the same or different, representing carbonyl, ester, amide, ether, or single bond; *** indicates the bonding position with other structures in the aforementioned main-chain polymer]; [Chem. 7] [In the aforementioned chemical formula (2D), ring G represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, spirocyclic rings, and aliphatic hydrocarbon rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are set as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, spirocyclic rings, and aliphatic hydrocarbon rings may have substituents; L13 and L14 may be the same or different, representing single bonds and alkyl chains with 1 to 6 carbon atoms; L15 and L16 may be the same or different, representing carbonyl groups, ester bonds, amide bonds, ether bonds, or single bonds; *** indicates the bonding position with other structures in the aforementioned main-chain polymer].

4. A main-chain polymer as described in any one of claims 1 to 3, wherein at least one of the main-chain polymers is terminated in a monocarboxylic acid ester represented by the following chemical formula (2'); [Chemical 8] [In the aforementioned chemical formula (2'), R10 represents a group consisting of an alkyl group having 1 to 20 substituted carbon atoms, a cycloalkyl group having 3 to 8 substituted carbon atoms, and an aromatic group having 3 to 12 substituted carbon atoms; ** represents the bonding position with other structures in the aforementioned main-chain polymer].

5. A resin composition comprising: 70-99.99% by weight of the main-chain polymer as described in any one of claims 1 to 3, and 0.01-30% by weight of a thermal reorientation accelerator.

6. A resin composition comprising: 70-99.99% by weight of the main-chain polymer as described in claim 4, and 0.01-30% by weight of a thermal reorientation accelerator.

7. A method for manufacturing a main-chain polymer as described in any one of claims 1 to 3, comprising polymerizing a raw material composition comprising a dihydroxy compound represented by the following chemical formula (1'): [Chemical 9] [In the aforementioned chemical formula (1'), R0, R1, R2, R3, and R4 independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1); Ar represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are designated as atoms constituting the ring, and these monocyclic aromatic rings, polycyclic aromatic rings, or condensed aromatic rings may have substituents]; [Chemical 10] [In the aforementioned chemical formula (Z1), Rz3 and Rz4 independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 8 carbon atoms; Arz represents a ring selected from the group consisting of monocyclic aromatic rings, polycyclic aromatic rings, and condensed aromatic rings, wherein atoms selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms are defined as the atoms constituting the ring. These monocyclic aromatic rings, polycyclic aromatic rings, or condensed aromatic rings may have substituents; the wavy part represents the bonding position with the part in formula (1) other than R0, R1, R2, R3, or R4.

8. A method for manufacturing a main-chain polymer as described in claim 7, characterized in that, when polymerizing a raw material composition comprising a dihydroxy compound represented by chemical formula (1'), a monocarboxylic acid derivative compound represented by any of the following chemical formulas (2-1) or (2-2) is further added: [Chemical 11] [In the aforementioned chemical formulas (2-1) or (2-2), R5a, R6a and R7 independently represent groups selected from the group consisting of alkyl groups having 1 to 20 substituted carbon atoms, cycloalkyl groups having 3 to 8 substituted carbon atoms, and aromatic groups having 3 to 12 substituted carbon atoms].

9. An optical film comprising: a main-chain polymer as described in any one of claims 1 to 3 or a resin composition as described in claim 5.

10. An optical film comprising: a main-chain polymer as described in claim 4 or a resin composition as described in claim 6.

11. The optical film as claimed in claim 9 or 10, wherein the phase difference (Re) satisfies the following equation (I): Re(450)≦Re(550)･･･(I) In equation (I), Re(450) represents the in-plane phase difference value measured at a wavelength of 450 nm, and Re(550) represents the in-plane phase difference value measured at a wavelength of 550 nm.

12. The optical film as described in claim 10, wherein the yellowness (YI) of a film thickness of 5 μm is less than 5%.

13. A method for manufacturing an optical film as described in any one of claims 9 to 12, wherein the film is irradiated with either polarized ultraviolet light or obliquely incident ultraviolet light.

14. The method for manufacturing the optical film as described in claim 13 further includes a heat treatment step.

15. A multilayer film comprising an optical film as described in any one of claims 9 to 12.

Images