Optical film and manufacturing method thereof

Abstract

The present invention provides an optical film comprising a polymer resin including imide repeat units and amide repeat units, the amide repeat units being contained in a ratio of 80% or more to the imide repeat units and the amide repeat units, and a method for producing such an optical film.

Description

[Technical Field]

[0001] The present invention relates to optical films containing a high proportion of amide repeat units and methods for making same. [Background technology]

[0002] In recent years, as display devices have become thinner, lighter, and more flexible, the use of optical films instead of glass as cover windows has been considered. To be used as cover windows for display devices, optical films must have excellent optical and mechanical properties. Therefore, it is necessary to develop optical films whose optical properties do not change even when used in external environments for long periods of time. Summary of the Invention [Problem to be solved by the invention]

[0003] An object of one embodiment of the present invention is to provide an optical film having a high degree of polymerization and containing a high proportion of amide repeat units.

[0004] Another embodiment of the present invention aims to provide an optical film having excellent optical and mechanical properties by having a high degree of polymerization and containing a high proportion of amide repeating units.

[0005] Another embodiment of the present invention provides a method for producing an optical film having an excellent degree of polymerization and a high proportion of amide repeat units. [Means for solving the problem]

[0006] To solve this problem, one embodiment of the present invention provides an optical film comprising a polymer resin including imide repeating units and amide repeating units, wherein the amide repeating units are contained in a ratio of 80% or more to the imide repeating units and the amide repeating units.

[0007] The optical film may contain 120 ppm (0.012 wt%) or less of chlorine (Cl) by weight, where the chlorine concentration is measured by ion chromatography of a chlorine (Cl) extract obtained by freeze-drying and powdering the optical film and extracting it with distilled water.

[0008] The optical film may contain 50 ppm (0.005 wt %) or less of chlorine (Cl) by weight.

[0009] The imide repeating unit may include a first repeating unit and a second repeating unit, the first repeating unit being an imide repeating unit obtained by a polymerization reaction between a first diamine compound and a dianhydride compound, and the second repeating unit being an imide repeating unit obtained by a polymerization reaction between a second diamine compound and the dianhydride compound.

[0010] The amide repeating unit may include a third repeating unit and a fourth repeating unit, and the third repeating unit may be an amide repeating unit obtained by a polymerization reaction between a first diamine compound and a dicarbonyl compound, and the fourth repeating unit may be an amide repeating unit obtained by a polymerization reaction between a second diamine compound and the dicarbonyl compound.

[0011] The first diamine compound is an aromatic diamine compound, and examples of the first diamine compound include bistrifluoromethylbenzidine (2,2'-bis(trifluoromethyl)benzidine, TFDB), 2,2-bis(4-(4-aminophenoxy)phenyl)hexafluoropropane (HFBAPP), bis(4-(4-aminophenoxy)phenyl)sulfone (BAPS), bis(4-(3-aminophenoxy)phenyl)sulfone (BAPSM), 4,4'-diaminodiphenylsulfone (4DDS), 3,3'-diaminodiphenylsulfone (3DDS), p-phenylenediamine (para-phenylene diamine, pPDA), m-phenylenediamine (metaphenylene diamine, mPDA), p-methylenedianiline (para-Methylene Dianiline, pMDA), m-methylenedianiline (meta-Methylene Dianiline, mMDA), 2,2-bis(4-(4-aminophenoxy)phenylpropane (BAPP), 4,4'-diaminodiphenylpropane (6HDA), 1,3-bis(4-aminophenoxy)benzene (134APB), 1,3-bis(3-aminophenoxy)benzene (133APB), 1,4-bis(4-aminophenoxy)biphenyl (BAPB), 4,4'-bis(4-amino-2-trifluoromethylphenoxy)biphenyl (6FAPBP), 3,3-diamino Amino-4,4-dihydroxydiphenyl sulfone (DABS), 2,2-bis(3-amino-4-hydroxyphenyl)propane (BAP), 4,4'-diaminodiphenylmethane (DDM), 4,4'-oxydianiline (4-ODA), 3,3'-oxydianiline (3-ODA), 2,2'-dimethyl-4,4'-(9-fluorenylidene)dianiline (MFDA), 9,9-bis(4-aminophenyl)fluorene (FDA), and 9,9-bis(3-fluoro-4-aminophenyl)fluorene (9,9-Bis(4-aminophenyl)fluorene).FFDA).

[0012] The second diamine compound is an aliphatic diamine compound, and may include at least one selected from the group consisting of 4,4'-methylenebiscyclohexylamine (MBCA), 1,3-bis(aminomethyl)cyclohexane, 1,4-cyclohexanediamine, bicyclo[2.2.1]heptanebis(methylamine), and cis, trans, and mixture isomers of the above compounds.

[0013] The dianhydride compounds include 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride (6FDA), 4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic anhydride (TDA), pyromellic acid dianhydride (1,2,4,5-benzene tetracarboxylic dianhydride, pyromellictic acid dianhydride, PMDA), benzophenone tetracarboxylic dianhydride (3,3,4,4-benzophenone tetracarboxylic dianhydride, BTDA), biphenyltetracarboxylic dianhydride (3,3,4,4-biphenyltetracarboxylic dianhydride, BPDA), oxydiphthalic dianhydride (4,4-oxydiphthalic dianhydride, The phthalic anhydride may contain one or more compounds selected from the group consisting of bis(3,4-dicarboxyphenyl)dimethylsilane dianhydride (SiDA), bis(3,4-dicarboxyphenyl)diphenyl sulfide dianhydride (BDSDA), sulfonyldiphthalic anhydride (SO2DPA), cyclobutane-1,2,3,4-tetracarboxylic dianhydride (CBDA), and 4,4'-(4,4'-Isopropylidenediphenoxy)bis(phthalic anhydride, 6HBDA).

[0014] The dicarbonyl compound may include at least one selected from the group consisting of phthaloyl chloride, terephthaloyl chloride (TPC), isophthaloyl chloride (IPC), 4,4'-biphenyldicarbonyl chloride (DPDOC), 4,4'-oxybis(benzoyl chloride) (OBBOC), and naphthalene-2,3-dicarbonyl dichloride.

[0015] The optical film may have a yellowness index of 4.0 or less.

[0016] The optical film may have a light transmittance of 88.50% or more.

[0017] Another embodiment of the present invention provides a display device including a display panel; and the optical film disposed on the display panel.

[0018] Another embodiment of the present invention provides a method for manufacturing an optical film, the method including: forming a first reaction solution using at least one of a first diamine compound and a second diamine compound, a dianhydride compound, a dicarbonyl compound, and a chlorine (Cl) acceptor; adding a dehydrating agent and an imidization catalyst to the first reaction solution and reacting them to form a second reaction solution; treating the second reaction solution to prepare a solid polymer resin; dissolving the solid polymer resin to prepare a polymer resin solution; and casting the polymer resin solution, wherein the content of the chlorine (Cl) acceptor is 4 to 7 times the content of the dicarbonyl compound on a molar basis.

[0019] The first diamine-based compound may be an aromatic diamine-based compound, and the second diamine-based compound may be an aliphatic diamine-based compound.

[0020] The content of the dicarbonyl compound may be 80 to 99 mole parts, and the content of the dianhydride compound may be 1 to 20 mole parts, relative to 100 mole parts of the total content of the first diamine compound and the second diamine compound.

[0021] The content of the first diamine compound may be 85 to 95 mole parts, and the content of the second diamine compound may be 5 to 15 mole parts, relative to 100 mole parts of the total content of the first diamine compound and the second diamine compound.

[0022] The chlorine (Cl) acceptor may include a cyclic ether compound.

[0023] The cyclic ether-based compound may include an epoxide-based compound, an oxetane-based compound, a tetrahydrofuran-based compound, and a tetrahydropyran-based compound.

[0024] The cyclic ether-based compound may include a propylene oxide-based compound.

[0025] The pH of the second reaction solution may be 8 to 9.

[0026] The polymer resin solution may have a pH of 6 to 7. [Effects of the Invention]

[0027] According to an embodiment of the present invention, by activating the polymerization reaction of a dicarbonyl compound, it is possible to provide a polymer resin with an excellent degree of polymerization even when a large amount of a dicarbonyl compound is added.

[0028] According to an embodiment of the present invention, a polymer resin having an excellent degree of polymerization can be provided by activating the polymerization reaction of an aliphatic diamine compound.

[0029] Another embodiment of the present invention aims to provide an optical film having excellent mechanical and optical properties.

[0030] Another embodiment of the present invention aims to provide optical films that contain a high proportion of amide repeat units.

[0031] The optical film according to another embodiment of the present invention has excellent optical and mechanical properties, and therefore, when used as a cover window of a display device, can effectively protect the display surface of the display device. [Brief explanation of the drawings]

[0032] [Figure 1] 10 is a cross-sectional view of a portion of a display device according to another embodiment of the present invention. [Figure 2] FIG. 2 is an enlarged cross-sectional view of a portion "P" in FIG. DETAILED DESCRIPTION OF THE INVENTION

[0033] Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings. However, the embodiments described below are merely presented for illustrative purposes to help a clear understanding of the present invention, and do not limit the scope of the present invention.

[0034] The shapes, sizes, ratios, angles, numbers, etc. disclosed in the drawings for illustrating the embodiments of the present invention are merely examples, and the present invention is not limited to the details shown in the drawings. The same components may be designated by the same reference numerals throughout the specification. When describing the present invention, if a detailed description of related publicly known technology is deemed to unnecessarily obscure the gist of the present invention, such a detailed description will be omitted.

[0035] When words such as "include," "have," and "be made" are used in this specification, other parts may be added unless the expression "only" is used. When an element is expressed as singular, it includes plural unless otherwise expressly stated. Furthermore, when interpreting an element, it is interpreted as including a margin of error even if there is no other explicit statement.

[0036] When describing a positional relationship, for example, when describing the positional relationship of two parts using terms such as "above," "on top," "below," or "beside," one or more other parts may be located between the two parts, unless the words "immediately" or "directly" are used.

[0037] Spatially relative terms such as "below," "beneath," "lower," "above," and "upper" may be used to easily describe the relationship of one element or component to another, as illustrated in the figures. Spatially relative terms should be understood to encompass different orientations of elements in use or operation in addition to the orientation depicted in the figures. For example, if an element depicted in the figures were flipped over, an element described as "below" or "beneath" another element would be positioned "above" the other element. Thus, the exemplary term "below" can encompass both an orientation of below and above. Similarly, the exemplary terms "top" or "upper" can encompass both an orientation of above and below.

[0038] When describing a temporal relationship, for example, when the temporal sequence is described using "after," "following," "next," or "before," it can also include cases where the sequence is not consecutive, unless the words "immediately" or "directly" are used.

[0039] Although terms such as "first," "second," etc. are used to describe various components, these components are not limited by these terms. These terms are used merely to distinguish one component from another. Therefore, a first component referred to below may also be a second component within the technical concept of the present invention.

[0040] The term "at least one" should be understood to include all possible combinations of one or more related items. For example, "at least one of the first, second, and third items" means not only the first, second, or third item, but also all possible combinations of two or more of the first, second, and third items.

[0041] The features of the various embodiments of the present invention may be partially or fully combined or combined with each other, and may be technically interlocked and driven in various ways, and each embodiment may be implemented independently of the other, or may be implemented together in a linked relationship.

[0042] An embodiment of the present invention provides an optical film. The optical film according to an embodiment of the present invention includes a polymer resin.

[0043] The polymer resin may be included in the film in various forms and shapes, such as a solid powder form, a dissolved form in a solution, or a matrix form solidified after dissolving in a solution, and any resin containing the same repeating units as in the present invention, regardless of its form and shape, can be considered to be the same as the polymer resin of the present invention. However, in general, the polymer resin in the film may be present in the form of a matrix solidified by coating a polymer resin solution and then drying it.

[0044] The polymer resin according to an embodiment of the present invention includes imide repeat units and amide repeat units, and therefore the optical film according to an embodiment of the present invention includes imide repeat units and amide repeat units.

[0045] According to an embodiment of the present invention, the imide repeat unit may include a first repeat unit and a second repeat unit, wherein the first repeat unit may be an imide repeat unit formed by a polymerization reaction between a first diamine compound and a dianhydride compound, and the second repeat unit may be an imide repeat unit formed by a polymerization reaction between a second diamine compound and a dianhydride compound.

[0046] According to an embodiment of the present invention, the amide repeat unit may include a third repeat unit and a fourth repeat unit, wherein the third repeat unit may be an amide repeat unit obtained by polymerization of a first diamine compound and a dicarbonyl compound, and the fourth repeat unit may be an amide repeat unit obtained by polymerization of a second diamine compound and a dicarbonyl compound.

[0047] However, the polymer resin according to an embodiment of the present invention is not limited thereto. The polymer resin according to an embodiment of the present invention may be prepared from a monomer component including other compounds in addition to the first diamine-based compound, the second diamine-based compound, the dianhydride-based compound, and the dicarbonyl-based compound. Therefore, the polymer resin according to an embodiment of the present invention may further include other repeating units in addition to the imide repeating unit and the amide repeating unit.

[0048] According to an embodiment of the present invention, the optical film may include a polyamide-imide based polymer. According to an embodiment of the present invention, the optical film may include a polyamide-imide based polymer resin. According to an embodiment of the present invention, the optical film may be a polyamide-imide based film.

[0049] According to an embodiment of the present invention, the first diamine-based compound may be an aromatic diamine-based compound.

[0050] In one embodiment of the present invention, the term "aromatic diamine compound" refers to a diamine in which an amino group is directly bonded to an aromatic ring, and the aromatic ring may contain an aliphatic group or other substituents as part of its structure. The aromatic ring may be a single ring, a bonded ring in which the single ring is connected directly or via a heteroatom, or a fused ring. The aromatic ring may include, but is not limited to, a benzene ring, a biphenyl ring, a naphthalene ring, an anthracene ring, and a fluorene ring.

[0051] According to one embodiment of the present invention, the first diamine-based compound may be represented by the following Chemical Formula 1:

[0052] <Chemical formula 1> JPEG0007811650000001.jpg1042

[0053] In Chemical Formula 1, A 1 represents a divalent aromatic organic group. An aromatic organic group is an organic group in which single bonds and double bonds are alternately linked to form a ring, thereby distributing pi electrons unevenly. For example, A 1 includes a divalent aromatic organic group having 4 to 40 carbon atoms. The hydrogen atoms in the aromatic organic group included in Chemical Formula 1 can be substituted with a halogen atom, a hydrocarbon group, or a hydrocarbon group substituted with a halogen element. The hydrocarbon group substituted with a hydrogen atom or the hydrocarbon group substituted with a halogen element may have 1 to 8 carbon atoms. For example, A 1 The hydrogen contained in can be substituted with -F, -CH3, -CF3, etc.

[0054] An optical film manufactured using a diamine-based compound in which a hydrogen atom is substituted with a fluorine-substituted hydrocarbon group can have excellent light transmittance and excellent processing properties.

[0055] A in Chemical Formula 1 1 may include, for example, a structure represented by any one of the following structural formulas: 1 is not limited to any one of the following structural formulas:

[0056] JPEG0007811650000002.jpg52148

[0057] In the structural formula, * indicates a bonding position. In the structural formula, X may independently be any one of a single bond, O, S, SO2, CO, CH2, C(CH3)2, and C(CF3)3. The bonding position of X to each ring is not particularly limited, but the bonding position of X to each ring may be, for example, a meta or para position.

[0058] According to an embodiment of the present invention, the first diamine-based compound may be bistrifluoromethylbenzidine (2,2'-bis(trifluoromethyl)benzidine, TFDB), 2,2-bis(4-(4-aminophenoxy)phenyl)hexafluoropropane (HFBAPP), bis(4-(4-aminophenoxy)phenyl)sulfone (BAPS), bis(4-(3-aminophenoxy)phenyl)sulfone (BAPSM), 4,4'-diaminodiphenylsulfone (4DDS), 3,3'-diaminodiphenylsulfone (3DDS), p-phenylenediamine (para-phenylene diamine, pPDA), m-phenylenediamine (metaphenylene diamine, mPDA), p-methylenedianiline (para-Methylene Dianiline, pMDA), m-methylenedianiline (meta-Methylene Dianiline, mMDA), 2,2-bis(4-(4-aminophenoxy)phenylpropane (BAPP), 4,4'-diaminodiphenylpropane (6HDA), 1,3-bis(4-aminophenoxy)benzene (134APB), 1,3-bis(3-aminophenoxy)benzene (133APB), 1,4-bis(4-aminophenoxy)biphenyl (BAPB), 4,4'-bis(4-amino-2-trifluoromethylphenoxy)biphenyl (6FAPBP), 3,3-diamino Amino-4,4-dihydroxydiphenyl sulfone (DABS), 2,2-bis(3-amino-4-hydroxyphenyl)propane (BAP), 4,4'-diaminodiphenylmethane (DDM), 4,4'-oxydianiline (4-ODA), 3,3'-oxydianiline (3-ODA), 2,2'-dimethyl-4,4'-(9-fluorenylidene)dianiline (MFDA), 9,9-bis(4-aminophenyl)fluorene (FDA), and 9,9-bis(3-fluoro-4-aminophenyl)fluorene (9,9-Bis(4-aminophenyl)fluorene).FFDA).

[0059] According to an embodiment of the present invention, the second diamine-based compound may be an aliphatic diamine-based compound.

[0060] In one embodiment of the present invention, the term "aliphatic diamine compound" refers to a diamine in which an amino group is directly bonded to an aliphatic group, and the structure may include an aromatic ring or other substituents. Aliphatic diamines may include cyclic aliphatic diamines and non-cyclic aliphatic diamines.

[0061] According to one embodiment of the present invention, the second diamine-based compound may be represented by the following Chemical Formula 2:

[0062] <Chemical formula 2> JPEG0007811650000003.jpg1043

[0063] In Chemical Formula 2, A 2 represents a divalent aliphatic organic group. For example, A 2 contains a divalent aliphatic organic group having 4 to 40 carbon atoms. The hydrogen atoms in the aliphatic organic group contained in Chemical Formula 2 can be substituted with a halogen atom, a hydrocarbon group, or a hydrocarbon group substituted with a halogen element. The hydrocarbon group substituted with a hydrogen atom or the hydrocarbon group substituted with a halogen element may have 1 to 8 carbon atoms. For example, A 2 The hydrogen contained in can be substituted with -F, -CH3, -CF3, etc.

[0064] An optical film manufactured using a diamine-based compound in which a hydrogen atom is substituted with a fluorine-substituted hydrocarbon group can have excellent light transmittance and excellent processing properties.

[0065] A in Chemical Formula 2 2 may include, for example, a structure represented by any one of the following structural formulas: 2is not limited to any one of the following structural formulas:

[0066] JPEG0007811650000004.jpg18127

[0067] In the structural formula, * indicates a bonding position. However, the amine group can be directly bonded to the bonding position, or can be bonded via an alkylene group having 1 to 3 carbon atoms. In the structural formula, Y may independently be any one of a single bond, O, S, SO2, CO, CH2, C(CH3)2, and C(CF3)3. The bonding position of Y to each ring is not particularly limited.

[0068] According to an embodiment of the present invention, the second diamine compound may include at least one selected from the group consisting of 4,4'-methylenebiscyclohexylamine (MBCA), 1,3-bis(aminomethyl)cyclohexane, 1,4-cyclohexanediamine, bicyclo[2.2.1]heptanebis(methylamine), and cis, trans, and mixture isomers of the foregoing compounds.

[0069] When a polymer resin contains repeating units derived from an aliphatic diamine compound, the yellowness index and light transmittance of the film can be improved compared to when the polymer resin contains only repeating units derived from an aromatic diamine compound. As a result, an optical film with excellent optical properties can be obtained. Since the benzene ring contained in the aromatic diamine compound causes the film to have a yellowish color, the yellowness index of the film can be reduced by using a larger amount of an aliphatic diamine compound than an aromatic diamine compound.

[0070] However, because aliphatic diamine compounds have strong basicity, they react with carboxylic acids to form salts. As a result, when using aliphatic diamine compounds, the polymerization reaction does not proceed smoothly using conventional polymerization methods, resulting in a problem of a decrease in the degree of polymerization of the resin. A decrease in the degree of polymerization of the resin can lead to a decrease in the optical properties of the film, making it unsuitable for use as an optical film.

[0071] According to one embodiment of the present invention, one method for increasing the degree of polymerization of a polymer resin while using an aliphatic diamine-based compound is to minimize the content of chlorine (Cl) contained in the polymer resin and film.

[0072] According to one embodiment of the present invention, the dianhydride-based compound can be represented by the following Chemical Formula 3:

[0073] <Chemical formula 3> JPEG0007811650000005.jpg4742

[0074] In Chemical Formula 3, A 3 represents a tetravalent organic group. For example, A 3 may contain a tetravalent organic group having 4 to 40 carbon atoms. The hydrogen atoms in the organic group contained in Chemical Formula 3 may be substituted with a halogen element, a hydrocarbon group, or a halogen-substituted hydrocarbon group. Here, the hydrocarbon group or halogen-substituted hydrocarbon group substituted with a hydrogen atom may have 1 to 8 carbon atoms.

[0075] A in Chemical Formula 3 3 may include, for example, a structure represented by any one of the following structural formulas:

[0076] JPEG0007811650000006.jpg72135

[0077] In the structural formula, * indicates a bonding position. In the structural formula, Z may independently be any one of a single bond, O, S, SO2, CO, (CH2)n, (C(CH3)2)n, and (C(CF3)2)n, where n may be a positive number of 1 to 5. The bonding position of Z to each ring is not particularly limited, and Z may be, for example, a meta or para position to each ring.

[0078] According to one embodiment of the present invention, the dianhydride compounds include 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride (6FDA), 4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic anhydride (TDA), pyromellic acid dianhydride (1,2,4,5-benzene tetracarboxylic dianhydride, PMDA), benzophenone tetracarboxylic dianhydride (3,3,4,4-benzophenone tetracarboxylic dianhydride, BTDA), biphenyltetracarboxylic dianhydride (3,3,4,4-biphenyltetracarboxylic dianhydride, BPDA), and oxydiphthalic dianhydride (4,4-oxydiphthalic dianhydride, The phthalic anhydride may contain one or more compounds selected from the group consisting of bis(3,4-dicarboxyphenyl)dimethylsilane dianhydride (SiDA), bis(3,4-dicarboxyphenyl)diphenyl sulfide dianhydride (BDSDA), sulfonyldiphthalic anhydride (SO2DPA), cyclobutane-1,2,3,4-tetracarboxylic dianhydride (CBDA), and 4,4'-(4,4'-Isopropylidenediphenoxy)bis(phthalic anhydride, 6HBDA).

[0079] According to an embodiment of the present invention, the monomers used in manufacturing the optical film may include a variety of dianhydride-based compounds.

[0080] Optical films manufactured using dianhydride-based compounds in which hydrogen atoms are substituted with fluorine-substituted hydrocarbon groups have excellent light transmittance and can have excellent processing properties.

[0081] According to one embodiment of the present invention, the dicarbonyl compound can be represented by the following Chemical Formula 4:

[0082] <Chemical formula 4> JPEG0007811650000007.jpg2752

[0083] In Chemical Formula 4, A 4 indicates a divalent group. For example, A 4 may contain a divalent organic group having 4 to 40 carbon atoms. 4 can also represent a carbon atom, a nitrogen atom, or an oxygen atom. The hydrogen atoms in the organic group included in Chemical Formula 4 can be substituted with a halogen element, a hydrocarbon group, or a fluorine-substituted hydrocarbon group. Here, the number of carbon atoms in the hydrocarbon group substituted with a hydrogen atom or the fluorine-substituted hydrocarbon group may be 1 to 8.

[0084] According to one embodiment of the present invention, the dicarbonyl compound may include at least one selected from the group consisting of phthaloyl chloride, terephthaloyl chloride (TPC), isophthaloyl chloride (IPC), 4,4'-biphenyldicarbonyl chloride (DPDOC), 4,4'-oxybis(benzoyl chloride) (OBBOC), and naphthalene-2,3-dicarbonyl dichloride.

[0085] The polymer resin according to an embodiment of the present invention may include a first repeating unit represented by the following Formula 5 and a second repeating unit represented by the following Formula 6:

[0086] <Chemical formula 5> JPEG0007811650000008.jpg5984

[0087] A in Chemical Formula 5 1 and A 3 is as already explained.

[0088] <Chemical formula 6> JPEG0007811650000009.jpg5885

[0089] A in Chemical Formula 6 2 and A 3 is as already explained.

[0090] The polymer resin according to an embodiment of the present invention may include a third repeating unit represented by the following Formula 7 and a fourth repeating unit represented by the following Formula 8:

[0091] <Chemical formula 7> JPEG0007811650000010.jpg3896

[0092] A in chemical formula 7 1 and A 4 is as already explained.

[0093] <Chemical formula 8> JPEG0007811650000011.jpg3897

[0094] A in chemical formula 8 2 and A 4 is as already explained.

[0095] According to one embodiment of the present invention, the content of the dicarbonyl compound used in the preparation of the optical film is 80 to 99 mole parts relative to 100 mole parts of the total content of the dianhydride compound and the dicarbonyl compound.

[0096] The content of the dianhydride compound is 1 to 20 parts by mole relative to 100 parts by mole of the total content of the dianhydride compound and the dicarbonyl compound.

[0097] Generally, when preparing a polymer resin, a "diamine compound" and a "dianhydride compound and a dicarbonyl compound" are added in a ratio of about 1:1. Therefore, when the "total content of the first diamine compound and the second diamine compound" is 100 mole parts, the "content of the dicarbonyl compound" can be expressed as 80 to 99 mole parts, and the "content of the dianhydride compound" can be expressed as 1 to 20 mole parts.

[0098] Furthermore, since the first and second repeat units are derived from a dianhydride compound, and the third and fourth repeat units are derived from a dicarbonyl compound, the total number of "third and fourth repeat units" contained in the polymer resin accounts for 80% to 99% of the total number of "total repeat units including the first to fourth repeat units," and the total number of "first and second repeat units" can also be expressed as 1% to 20% of the total number of "total repeat units including the first to fourth repeat units."

[0099] When the total number of the third repeating units and the fourth repeating units is 80% to 99% of the total number of repeating units including the first to fourth repeating units, yellowness and haze can be reduced, light transmittance can be improved, and mechanical properties can also be improved. That is, by including a larger amount of amide repeating units than imide repeating units, a colorless and transparent film can be produced while maintaining insolubility, chemical resistance, heat resistance, radiation resistance, low-temperature properties, etc.

[0100] However, when a large amount of dicarbonyl compound is added to form a large amount of amide repeating units, the dicarbonyl compound gels, which causes a problem that the polymerization reaction does not proceed satisfactorily.

[0101] According to one embodiment of the present invention, one method for improving the degree of polymerization of a polymer resin using an aliphatic diamine-based compound and a large amount of a dicarbonyl-based compound is to minimize the content of chlorine (Cl) contained in the polymer resin and the optical film.

[0102] According to one embodiment of the present invention, the chlorine (Cl) content in a polymer resin is minimized. The degree of polymerization of the polymer resin with the minimized chlorine (Cl) content can be improved. The chlorine (Cl) content of an optical film including the polymer resin with the minimized chlorine (Cl) content can also be minimized.

[0103] The present inventors have confirmed that if chlorine (Cl) atoms remain in a polymer resin, the degree of polymerization of the polymer resin decreases, and that the remaining chlorine (Cl) atoms in an optical film containing the same also decrease. Specifically, if hydrochloric acid (HCl) generated during the optical film manufacturing process is not sufficiently removed and remains in a reaction solution for manufacturing the optical film, for example, a polymer resin precursor solution, the acidity of the reaction solution increases, reducing reactivity and potentially causing degradation of the polymer. Furthermore, during the chemical or thermal imidization process in the optical film manufacturing process, hydrochloric acid (HCl) reacts with water (HO) to generate hydronium ions (HO). + ) and chloride ions (Cl -), which may induce side reactions such as the formation of chlorine (Cl) atoms, resulting in a deterioration of the optical properties of the optical film. Furthermore, when an optical film containing chlorine (Cl) atoms is irradiated with heat and light, photo-initiated reactions by the chlorine (Cl) atoms may accelerate the decomposition or degradation of the polymer contained in the film or cause changes in the chemical structure of the polymer resin. In this way, if the chemical structure of the polymer resin that constitutes the optical film is decomposed or deteriorated and changed by heat treatment and light irradiation, the optical properties of the optical film may be reduced.

[0104] An optical film according to an embodiment of the present invention may contain chlorine (Cl) of 120 ppm or less by weight. According to an embodiment of the present invention, 120 ppm may correspond to 0.012 wt %. According to an embodiment of the present invention, ppm is a unit for measuring the concentration of chloride ions contained in an optical film by weight. According to an embodiment of the present invention, the chlorine (Cl) concentration may be measured using ion chromatography and calculated using the concentration of an ion chromatography standard solution.

[0105] According to one embodiment of the present invention, after freeze-drying and powdering the optical film, chlorine (Cl) is extracted from the optical film using distilled water to obtain a chlorine (Cl) extract, and the obtained chlorine (Cl) extract is subjected to ion chromatography analysis to measure the chlorine (Cl) concentration in the optical film. The powdered optical film is mixed with distilled water at a ratio of, for example, 5% by weight, and chlorine (Cl) is extracted from the mixture of the powdered optical film and distilled water.

[0106] According to one embodiment of the present invention, the chlorine (Cl) concentration can also be referred to as the concentration of chloride ions extracted with water (H2O).

[0107] More specifically, according to one embodiment of the present invention, a 50 μm-thick optical film is cut into approximately 0.5 cm x 0.5 cm pieces, freeze-dried, and powdered. Then, a chlorine (Cl) extract is obtained by ultrasonically extracting the chlorine extract using distilled water for two hours. The chlorine content can be evaluated by performing ion chromatography on the chlorine extract and calculating the chlorine concentration. The ion chromatography analysis can be performed using a Dionex ICS-2000 Ion Chromatography System equipped with two columns: IonPac AS18 Analytical (4 x 250 mm) + AG18 Guard (4 x 50 mm) and an eluent: Dionex EGC-KOH III Cartridge.

[0108] The optical film according to an embodiment of the present invention has a low chlorine (Cl) concentration and can have excellent thermal and optical stability. The polymer structure in the optical film according to an embodiment of the present invention is not damaged or decomposed even when subjected to heat treatment or exposed to light for a long period of time, and the optical film can maintain excellent optical and mechanical properties.

[0109] According to an embodiment of the present invention, the content of chlorine (Cl) contained in the optical film can be minimized to prevent deterioration of the optical and mechanical properties of the optical film.

[0110] The optical film according to an embodiment of the present invention may contain 120 ppm (0.012 wt%) or less of chlorine (Cl) by weight, and may contain 50 ppm (0.005 wt%) or less of chlorine (Cl). Also, the optical film according to an embodiment of the present invention may contain 0.1 to 120 ppm (0.00001 to 0.012 wt%) of chlorine (Cl), and may contain 1 to 120 ppm (0.0001 to 0.012 wt%) of chlorine (Cl).

[0111] When an optical film contains 120 ppm or less of chlorine (Cl) by weight, it is possible to produce an optical film with an excellent degree of polymerization of the polymer resin, and it is possible to minimize or prevent the deterioration of the optical properties of the optical film caused by chlorine (Cl).

[0112] According to one embodiment of the present invention, the term chlorine (Cl) refers to both chlorine atoms and chlorine ions (Cl - In addition, according to an embodiment of the present invention, chlorine (Cl) can bond with other atoms to form a molecule, and the chlorine atom contained in the molecule is included in chlorine (Cl) according to an embodiment of the present invention.

[0113] The optical film according to an embodiment of the present invention may contain 5 to 120 ppm (0.0005 to 0.012 wt %) of chlorine (Cl).

[0114] As previously described, hydrochloric acid (HCl) may be generated during the manufacturing process of an optical film. If the hydrochloric acid generated during the manufacturing process of an optical film is not removed, chlorine (Cl) may remain in the resulting film. Therefore, according to one embodiment of the present invention, a chlorine (Cl) acceptor is used to remove the hydrochloric acid generated during the manufacturing process of the optical film in order to minimize the amount of chlorine (Cl) remaining in the optical film.

[0115] The chlorine (Cl) acceptors react with hydrochloric acid (HCl) to form chlorine (Cl) compounds during the optical film manufacturing process, and are then removed during the optical film manufacturing process. However, some of the chlorine (Cl) acceptors may not react with hydrochloric acid and may not be removed during the optical film manufacturing process. Therefore, the film according to one embodiment of the present invention may contain a trace amount of chlorine (Cl) acceptors.

[0116] In one embodiment of the present invention, the chloride (Cl) acceptor is hydrochloric acid (HCl) or chloride ions (Cl - ) and chloride (Cl) acceptors are substances that can react with hydrochloric acid (HCl) or chloride ions (Cl). -), and then can be removed in a subsequent step during the manufacturing process of the optical film.

[0117] The chlorine (Cl) acceptor can serve to remove hydrochloric acid produced during the polymerization process, for example, by reacting with hydrochloric acid to form a salt or a halohydrine compound.

[0118] According to an embodiment of the present invention, a cyclic ether-based compound may be used as a chlorine (Cl) acceptor. The cyclic ether-based compound may include, for example, at least one of an epoxide-based compound, an oxetane-based compound, a tetrahydrofuran-based compound, and a tetrahydropyran-based compound.

[0119] The optical film according to an embodiment of the present invention may contain a cyclic ether-based compound in an amount of 0.1 to 30 ppm by weight, or 0.1 to 12 ppm by weight.

[0120] According to one embodiment of the present invention, an epoxide-based compound represented by the following Formula 9 may be used as a chlorine (Cl) acceptor.

[0121] <Chemical formula 9> JPEG0007811650000012.jpg3764

[0122] In Chemical Formula 9, R 1 , R 2 , R 3 and R 4 may each independently be either hydrogen or an organic group having 1 to 20 carbon atoms. 1 , R 2 , R3 and R 4 may each independently be hydrogen or a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms. 1 , R 2 , R 3 and R 4 may each independently be hydrogen or an alkyl group having 1 to 10 carbon atoms.

[0123] According to one embodiment of the present invention, among the epoxide-based compounds represented by Formula 9, propylene oxide (PO) can be used as a chlorine (Cl) acceptor.

[0124] The epoxide-based compound used as a chlorine (Cl) acceptor can react with hydrochloric acid (HCl) or chlorine (Cl) according to the following reaction scheme 1:

[0125] <Reaction Scheme 1> JPEG0007811650000013.jpg73140

[0126] In reaction scheme 1, R 1 , R 2 , R 3 and R 4 As explained above, in Reaction Scheme 1, only structural isomers due to differences in the carbon position to which chlorine (Cl) is bonded are shown, but partial stereoisomers or enantiomers due to stereocenters (chiral centers) can also be produced.

[0127] In one embodiment of the present invention, the reaction product of the chlorine (Cl) acceptor and hydrochloric acid (HCl) is removed during the manufacturing process of the optical film. As a result, chlorine (Cl) can be removed. However, the reaction product of the chlorine (Cl) acceptor and chlorine (Cl) may not be removed and may remain in the film. Therefore, the optical film according to one embodiment of the present invention may contain the reaction product of the chlorine (Cl) acceptor and hydrochloric acid (HCl) or chlorine (Cl).

[0128] When propylene oxide (PO) is used as a chlorine (Cl) acceptor, the chlorine acceptor can react with hydrochloric acid (HCl) according to the following reaction formula 2:

[0129] <Reaction Scheme 2> JPEG0007811650000014.jpg53134

[0130] According to one embodiment of the present invention, the total number of the first repeating unit and the third repeating unit may be 85% to 95% of the total number of repeating units including the first to fourth repeating units. That is, the content of the first diamine compound used in manufacturing the optical film may be 85 to 95 mole parts per 100 mole parts of the total content of the first diamine compound and the second diamine compound, and the content of the second diamine compound may be 5 to 15 mole parts per 100 mole parts of the total content of the first diamine compound and the second diamine compound.

[0131] If the content of the second diamine compound, which is an aliphatic diamine compound, is less than 5%, the optical properties of the optical film may be degraded, whereas if it exceeds 15%, the mechanical properties of the optical film may be degraded.

[0132] According to one embodiment of the present invention, the number average molecular weight (M n ) can be 150,000 or more.

[0133] Aliphatic diamine compounds and dicarbonyl compounds have low reactivity due to side reactions or gelation, and the degree of polymerization of polymer resins containing aliphatic diamine compounds and dicarbonyl compounds tends to decrease. The number average molecular weight is proportional to the degree of polymerization, and as the degree of polymerization decreases, the number average molecular weight of the polymer resin also decreases.

[0134] If the number average molecular weight of the polymer resin is less than 150,000, the degree of polymerization decreases, the number of terminal groups of the polymer chain increases, and the physical properties of the resin deteriorate.

[0135] According to an embodiment of the present invention, the optical film may have optical transparency and flexibility. For example, the optical film according to an embodiment of the present invention may have bending, folding, and rollable properties.

[0136] The optical film according to an embodiment of the present invention may have a yellowness index of 4.0 or less, or may have a yellowness index of 3.0 or less, or may have a yellowness index of 2.0 or less.

[0137] The optical film according to an embodiment of the present invention may have a light transmittance of 88.50% or more. Furthermore, the optical film according to an embodiment of the present invention may have a light transmittance of 90% or more, or may have a light transmittance of 91% or more, based on a thickness of 50 μm.

[0138] The yellowness index and light transmittance can be measured in the wavelength range of 360 to 740 nm using a spectrophotometer in accordance with standard ASTM E 313. For example, a CM-3700D manufactured by KONICA MINOLTA can be used as the spectrophotometer.

[0139] The optical film according to an embodiment of the present invention can be applied to a display device to protect the display surface of a display panel. The optical film according to an embodiment of the present invention can have a thickness sufficient to protect the display panel. For example, the optical film can have a thickness of 10 to 100 μm.

[0140] Hereinafter, a display device using an optical film according to an embodiment of the present invention will be described with reference to FIGS.

[0141] FIG. 1 is a cross-sectional view of a part of a display device (200) according to another embodiment of the present invention, and FIG. 2 is an enlarged cross-sectional view of part "P" in FIG.

[0142] Referring to FIG. 1, a display device (200) according to another embodiment of the present invention includes a display panel (501) and an optical film (100) on the display panel (501).

[0143] 1 and 2, the display panel 501 includes a substrate 510, a thin film transistor (TFT) on the substrate 510, and an organic light emitting element 570 connected to the thin film transistor (TFT). The organic light emitting element 570 includes a first electrode 571, an organic light emitting layer 572 on the first electrode 571, and a second electrode 573 on the organic light emitting layer 572. The display device 200 disclosed in FIGS. 1 and 2 is an organic light emitting display device.

[0144] The substrate 510 can be made of glass or plastic. Specifically, the substrate 510 can be made of plastic such as polyimide resin. Although not shown, a buffer layer can be disposed on the substrate 510.

[0145] The thin film transistor (TFT) is disposed on the substrate 510. The thin film transistor (TFT) includes a semiconductor layer 520, a gate electrode 530 insulated from the semiconductor layer 520 and overlapping at least a portion of the semiconductor layer 520, a source electrode 541 connected to the semiconductor layer 520, and a drain electrode 542 spaced apart from the source electrode 541 and connected to the semiconductor layer 520.

[0146] 2, a gate insulating layer 535 is disposed between the gate electrode 530 and the semiconductor layer 520. An interlayer insulating layer 551 may be disposed on the gate electrode 530, and a source electrode 541 and a drain electrode 542 may be disposed on the interlayer insulating layer 551.

[0147] The planarization film (552) is disposed on the thin film transistor (TFT) and flattens the top of the thin film transistor (TFT).

[0148] The first electrode 571 is disposed on the planarization film 552. The first electrode 571 is connected to the thin film transistor (TFT) through a contact hole formed in the planarization film 552.

[0149] The bank layer (580) is disposed on a part of the first electrode (571) and the planarization film (552) to define a pixel area or a light-emitting area. For example, the bank layer (580) is disposed in a matrix structure in the boundary area between multiple pixels, so that the pixel area can be defined by the bank layer (580).

[0150] The organic light-emitting layer (572) is disposed on the first electrode (571). The organic light-emitting layer (572) may also be disposed on the bank layer (580). The organic light-emitting layer (572) may include a single light-emitting layer, or may include two or more light-emitting layers stacked one above the other. The organic light-emitting layer (572) may emit light having one of red, green, and blue colors, or may emit white light.

[0151] A second electrode (573) is disposed on the organic light-emitting layer (572).

[0152] The first electrode (571), the organic light emitting layer (572), and the second electrode (573) are stacked to form the organic light emitting element (570).

[0153] Although not shown, when the organic light emitting layer 572 emits white light, each pixel may include a color filter for filtering the white light emitted from the organic light emitting layer 572 by wavelength. The color filter is formed on the path of light.

[0154] A thin film encapsulation layer 590 may be disposed on the second electrode 573. The thin film encapsulation layer 590 may include at least one organic film and at least one inorganic film, and the at least one organic film and the at least one inorganic film may be alternately disposed.

[0155] An optical film (100) is disposed on the display panel (501) having the above-described laminated structure.

[0156] Hereinafter, a method for manufacturing an optical film according to an embodiment of the present invention will be described.

[0157] A method for manufacturing an optical film according to one embodiment of the present invention includes: forming a first reaction solution using at least one of a first diamine compound and a second diamine compound, a dianhydride compound, a dicarbonyl compound, and a chlorine (Cl) acceptor; adding a dehydrating agent and an imidization catalyst to the first reaction solution and reacting them to form a second reaction solution; treating the second reaction solution to produce a solid polymer resin; dissolving the solid polymer resin to produce a polymer resin solution; and casting the polymer resin solution. Each step will be described in detail below.

[0158] First, a first reaction solution is formed using at least one of a first diamine compound and a second diamine compound, a dianhydride compound, a dicarbonyl compound, and a chlorine (Cl) acceptor.

[0159] Examples of solvents that can be used to prepare the first reaction solution include aprotic polar organic solvents such as dimethylacetamide (DMAc, N,N-dimethylacetamide), dimethylformamide (DMF, N,N-dimethylformamide), methylpyrrolidone (NMP, 1-methyl-2-pyrrolidinone), m-cresol, tetrahydrofuran (THF, tetrahydrofuran), chloroform, and methyl ethyl ketone (MEK), as well as mixtures thereof. However, the solvents used in embodiments of the present invention are not limited to these, and other solvents may also be used.

[0160] According to an embodiment of the present invention, the first diamine-based compound may be an aromatic diamine-based compound, and the compound of Formula 1 described above may be used as the first diamine-based compound.

[0161] According to an embodiment of the present invention, the second diamine-based compound may be an aliphatic diamine-based compound, and the compound of Formula 2 described above may be used as the second diamine-based compound.

[0162] According to one embodiment of the present invention, the compound of Formula 3 described above can be used as the dianhydride-based compound.

[0163] According to one embodiment of the present invention, the compound of Formula 4 described above can be used as the dicarbonyl compound.

[0164] For example, the first diamine compounds include bistrifluoromethylbenzidine (2,2'-bis(trifluoromethyl)benzidine, TFDB), 2,2-bis(4-(4-aminophenoxy)phenyl)hexafluoropropane (HFBAPP), bis(4-(4-aminophenoxy)phenyl)sulfone (BAPS), bis(4-(3-aminophenoxy)phenyl)sulfone (BAPSM), 4,4'-diaminodiphenylsulfone (4DDS), 3,3'-diaminodiphenylsulfone (3DDS), p-phenylenediamine (para-phenylene diamine, pPDA), m-phenylenediamine (metaphenylene diamine, mPDA), p-methylenedianiline (para-Methylene Dianiline, pMDA), m-methylenedianiline (meta-Methylene Dianiline, mMDA), 2,2-bis(4-(4-aminophenoxy)phenylpropane (BAPP), 4,4'-diaminodiphenylpropane (6HDA), 1,3-bis(4-aminophenoxy)benzene (134APB), 1,3-bis(3-aminophenoxy)benzene (133APB), 1,4-bis(4-aminophenoxy)biphenyl (BAPB), 4,4'-bis(4-amino-2-trifluoromethylphenoxy)biphenyl (6FAPBP), 3,3-diamino These include 4,4'-amino-dihydroxydiphenyl sulfone (DABS), 2,2-bis(3-amino-4-hydroxyphenyl)propane (BAP), 4,4'-diaminodiphenylmethane (DDM), 4,4'-oxydianiline (4-ODA), 3,3'-oxydianiline (3-ODA), 2,2'-dimethyl-4,4'-(9-fluorenylidene)dianiline (MFDA), 9,9-bis(4-aminophenyl)fluorene (FDA), and 9,9-bis(3-fluoro-4-aminophenyl)fluorene (FFDA).

[0165] For example, the second diamine compounds include 4,4'-methylenebiscyclohexylamine (MBCA), 1,3-bis(aminomethyl)cyclohexane, 1,4-cyclohexanediamine, bicyclo[2.2.1]heptanebis(methylamine), and cis, trans, and mixture isomers of the above compounds.

[0166] For example, dianhydride compounds include 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride (6FDA), 4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic anhydride (TDA), pyromellic acid dianhydride (1,2,4,5-benzene tetracarboxylic dianhydride, pyromellictic acid dianhydride, PMDA), benzophenone tetracarboxylic dianhydride (3,3,4,4-Benzophenone tetracarboxylic dianhydride, BTDA), biphenyltetracarboxylic dianhydride (3,3,4,4-Biphenyltetracarboxylic dianhydride, BPDA), and oxydiphthalic dianhydride (4,4-Oxydiphthalic dianhydride, These include bis(3,4-dicarboxyphenyl)dimethyl-silane dianhydride (SiDA), bis(3,4-dicarboxyphenoxy)diphenyl sulfide dianhydride (BDSDA), sulfonyldiphthalic anhydride (SO2DPA), cyclobutane-1,2,3,4-tetracarboxylic dianhydride (CBDA), and 4,4'-(4,4'-Isopropylidenediphenoxy)bis(phthalic anhydride, 6HBDA).

[0167] For example, dicarbonyl compounds include phthaloyl chloride, terephthaloyl chloride (TPC), isophthaloyl chloride (IPC), 4,4'-biphenyldicarbonyl chloride (DPDOC), 4,4'-oxybis(benzoyl chloride) (OBBOC), and naphthalene-2,3-dicarbonyl dichloride.

[0168] The first diamine compound, the second diamine compound, the dianhydride compound, and the dicarbonyl compound can each be used alone or in combination of two or more kinds.

[0169] According to one embodiment of the present invention, 80 to 99 mole parts of the dicarbonyl compound and 1 to 20 mole parts of the dianhydride compound may be used relative to 100 mole parts of the total content of the first diamine compound and the second diamine compound.

[0170] The effect of the amount of dicarbonyl compound added is as explained above.

[0171] According to one embodiment of the present invention, 85 to 95 mole parts of the first diamine compound and 5 to 15 mole parts of the second diamine compound may be used, based on 100 mole parts of the total content of the first diamine compound and the second diamine compound.

[0172] The effect of the amount of the first diamine compound added is as described above.

[0173] Chlorine (Cl) compounds may be generated during the reaction of the first diamine compound and the second diamine compound with the dicarbonyl compound. To remove the chlorine compounds, a chlorine (Cl) acceptor is used in the first reaction solution formation process, according to one embodiment of the present invention.

[0174] According to an embodiment of the present invention, a cyclic ether-based compound may be used as a chlorine (Cl) acceptor. The cyclic ether-based compound may include, for example, at least one of an epoxide-based compound, an oxetane-based compound, a tetrahydrofuran-based compound, and a tetrahydropyran-based compound.

[0175] According to one embodiment of the present invention, an epoxide-based compound represented by Chemical Formula 9 can be used as a chlorine (Cl) acceptor.

[0176] <Chemical formula 9> JPEG0007811650000015.jpg3764

[0177] In Chemical Formula 9, R 1 , R 2 , R 3 and R 4 may each independently be either hydrogen or an organic group having 1 to 20 carbon atoms. 1 , R 2 , R 3 and R 4 may each independently be hydrogen or a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms. 1 , R 2 , R 3 and R 4 may each independently be hydrogen or an alkyl group having 1 to 10 carbon atoms.

[0178] The epoxide-based compound used as a chlorine (Cl) acceptor can react with hydrochloric acid (HCl) according to Reaction Scheme 1. This allows the hydrochloric acid (HCl) to be removed from the first reaction solution.

[0179] <Reaction Scheme 1> JPEG0007811650000016.jpg73140

[0180] R in Reaction Scheme 1 1 , R 2 , R 3 and R 4 As explained above, in Reaction Scheme 1, only structural isomers due to differences in the carbon position to which chlorine (Cl) is bonded are shown, but partial stereoisomers or enantiomers due to stereocenters (chiral centers) can also be produced.

[0181] According to one embodiment of the present invention, propylene oxide (PO) among epoxide-based compounds can be used as a chlorine (Cl) acceptor.

[0182] When propylene oxide (PO) is used as a chlorine (Cl) acceptor, hydrochloric acid (HCl) can be removed according to the following reaction scheme 2:

[0183] <Reaction Scheme 2> JPEG0007811650000017.jpg53134

[0184] According to one embodiment of the present invention, the content of the chlorine (Cl) acceptor can be 4 to 7 times the content of the dicarbonyl compound on a molar basis. Considering the reaction between a diamine compound, particularly an aliphatic diamine compound, and a dicarbonyl compound, theoretically, if the content of the chlorine (Cl) acceptor is twice that of the dicarbonyl compound, the hydrochloric acid (HCl) produced by the reaction of the diamine compound and the dicarbonyl compound can be removed by the chlorine acceptor. However, the inventors have confirmed that when the content of the chlorine (Cl) acceptor is less than four times the number of moles of the dicarbonyl compound, the reaction between the chlorine (Cl) acceptor and hydrochloric acid (HCl) does not proceed sufficiently, resulting in a decrease in the efficiency of chlorine (Cl) removal. Furthermore, when a chlorine (Cl) acceptor exceeding seven times the number of moles of the dicarbonyl compound is used, the degree of polymerization decreases due to the excessive amount of chlorine (Cl) acceptor. Therefore, according to one embodiment of the present invention, the content of the chlorine (Cl) acceptor is adjusted to 4 to 7 times the content of the dicarbonyl compound in terms of mole number.

[0185] According to one embodiment of the present invention, the first reaction solution contains polyamic acid and polyamide repeating units. Polyamic acid is a precursor of polyimide.

[0186] Next, a dehydrating agent and an imidization catalyst are added to the first reaction liquid and reacted to form a second reaction liquid.

[0187] In the process of forming the second reaction solution, a part of the amic acid is imidized to form imide repeating units.

[0188] According to one embodiment of the present invention, a dehydrating agent and an imidization catalyst are added to the first reaction solution, and then the mixture is refluxed and stirred for 30 minutes to 2 hours at a temperature of 60 to 80° C. As a result, a second reaction solution is formed.

[0189] As the dehydrating agent, acid anhydrides such as acetic anhydride, propionic anhydride, isobutyric anhydride, pivalic anhydride, butyric anhydride, and isovaleric anhydride can be used.

[0190] As the imidization catalyst, a tertiary amine such as isoquinoline, β-picoline, or pyridine can be used.

[0191] The pH of the second reaction solution can be adjusted by the chlorine (Cl) acceptor and the imidization catalyst. According to one embodiment of the present invention, the second reaction solution can have a pH of 8 or higher.

[0192] According to one embodiment of the present invention, the content of the chlorine (Cl) acceptor added during the formation of the first reaction solution can be adjusted so that the pH of the second reaction solution is 8 to 9. According to one embodiment of the present invention, the second reaction solution has a pH of 8 to 9.

[0193] When the second reaction solution is in a weakly basic state with a pH of about 8 to 9, it can be said that all or most of the hydrochloric acid (HCl) generated during the formation of the first reaction solution has reacted with a chlorine (Cl) acceptor.

[0194] If the pH of the second reaction liquid is less than 8, the hydrochloric acid (HCl) produced during the formation of the first reaction liquid is not sufficiently removed, and chlorine (Cl) and chlorine compounds derived from the remaining hydrochloric acid (HCl) are likely to remain in the optical film.

[0195] When the pH of the second reaction liquid is taken into consideration, the imidization catalyst can be used in an amount 2 to 7 times the number of moles of the dianhydride compound.

[0196] The second reaction liquid is then treated to produce a solid state polymer resin.

[0197] To produce a solid polymer resin, a solvent can be added to the second reaction solution. Examples of the solvent include ethanol, methanol, and hexane. The solvent can be used alone or in combination of two or more solvents.

[0198] When a solvent that is well miscible with the polymerization solvent and has low polarity is added to the second reaction solution, a powdery solid polymer resin precipitates. The precipitate is filtered and dried to obtain a high-purity solid polymer resin. When the liquid components are removed during the filtration process, unreacted monomers, oligomers, and additives, as well as reaction by-products such as the reaction product of hydrochloric acid (HCl) and a chlorine (Cl) acceptor, are also removed. The solid polymer resin thus obtained contains no or only trace amounts of chlorine (Cl). The polymer resin may be a polyamide-imide resin containing imide repeating units and amide repeating units.

[0199] Next, the solid polymer resin is dissolved to prepare a polymer resin solution. This step is also called a re-dissolving step.

[0200] The solvent for dissolving the solid polymer resin may be the same as the solvent used in the polymerization process. For example, aprotic polar organic solvents such as dimethylacetamide (DMAc), dimethylformamide (DMF), 1-methyl-2-pyrrolidinone (NMP), m-cresol, tetrahydrofuran (THF), chloroform, and methyl ethyl ketone (MEK), as well as mixtures thereof, may be used to dissolve the solid polymer resin. However, the solvents used in the present invention are not limited to these examples, and other known solvents may also be used.

[0201] According to one embodiment of the present invention, the reconstituted polymer resin solution may have a pH of 6 to 7. According to one embodiment of the present invention, the polymer resin solution may have weak acidity or weak acidity close to neutral. Since the second reaction solution is prepared in a weakly basic state of pH 8 to 9, the polymer resin solution may exhibit a weak acidity of pH 6 to 7.

[0202] Next, the polymer resin solution is cast.

[0203] A cast substrate is used for casting. There is no particular limitation on the type of the cast substrate. The cast substrate may be a glass substrate, an aluminum substrate, a stainless steel (SUS) substrate, a Teflon substrate, or the like. According to one embodiment of the present invention, a glass substrate may be used as the cast substrate.

[0204] Specifically, casting is performed by applying a polymer resin solution to a casting substrate, and a coater, a blade, or the like can be used for casting.

[0205] After casting the polymer resin solution, the polymer resin coating film can be produced by drying it at a temperature ranging from 80 to 120°C while increasing the temperature at a rate of 2°C / min. The coating film produced in this way can be considered an intermediate for optical films. The coating film is pulled tightly and fixed to a pin-shaped tenter, and then heat-treated while increasing the temperature from 120°C to 250 to 350°C at a rate of 3°C / min. Once the maximum film-forming temperature is reached, an additional heat treatment of 10 to 30 minutes can be performed in an isothermal atmosphere. As a result, an optical film can be produced.

[0206] The present invention will be described in more detail below with reference to illustrative examples and comparative examples, but the present invention is not limited to the examples and comparative examples described below.

[0207] Example 1 A 1 L reactor equipped with a stirrer, nitrogen injector, dropping funnel, temperature controller, and condenser was charged with 451.63 g of DMAc (N,N-dimethylacetamide) while passing nitrogen through. The temperature of the reactor was then adjusted to 25°C. 45.37 g (0.85 mol%) of TFDB as a first diamine compound was then dissolved and maintained at 25°C. 5.26 g (0.015 mol%) of MBCA as a second diamine compound was then added and dissolved, and the mixture was allowed to react for 1 hour. After the first and second diamine compounds were dissolved, 14.81 g (0.20 mol%) of 6FDA was added and the mixture was allowed to react for 1 hour. The reactor temperature was then lowered to 5°C, and 27.07 g (0.80 mol%) of TPC and 34.85 g of propylene oxide were added and stirred for 1 hour to completely dissolve and react, forming a first reaction solution.

[0208] After the polymerization reaction was completed, 5.80 g of pyridine and 7.49 g of acetic anhydride were added to the first reaction solution and stirred for 30 minutes, then stirred again at 80° C. for 30 minutes, and cooled to room temperature to obtain a second reaction solution.

[0209] Methanol was added to the resulting second reaction solution to cause precipitation, and the precipitate was filtered to produce a white solid polymer resin. The resulting polymer resin was in the form of a solid powder.

[0210] The obtained polymer resin in a solid powder state was dissolved in DMAc to a concentration of 12.7 wt % to prepare a polymer resin solution.

[0211] The prepared polymer resin solution was cast onto a substrate. A cast substrate was used for casting. There is no particular limitation on the type of the cast substrate. The cast substrate may be a glass substrate, a stainless steel (SUS) substrate, a Teflon substrate, or the like. According to one embodiment of the present invention, a glass substrate may be used as the cast substrate.

[0212] Specifically, the polymer resin solution was applied to a glass substrate using a Mayer bar coater, and the temperature was raised from 80° C. to 120° C., followed by heat treatment for 17 minutes to obtain an optical film.

[0213] The produced optical film was peeled off from the glass substrate and fixed to a frame with pins.

[0214] The frame with the optical film fixed was placed in a hot air oven and slowly heated from 120°C to 250°C for 2 hours, then gradually cooled and dried. The dried optical film was then heat-treated again at 230°C for 5 minutes, resulting in an optical film with a thickness of 50 μm.

[0215] <Examples 2 to 9> Polymer resins of Examples 2 to 9 were prepared in the same manner as in Example 1, except that the type and / or content of the first diamine compound, the type and / or content of the second diamine compound, the content of the dianhydride compound, the type and / or content of the dicarbonyl compound, and the contents of DMAc, propylene oxide, pyridine, and acetic anhydride were changed. Then, polymer resin solutions and optical films of Examples 2 to 9 were prepared in the same manner as in Example 1.

[0216] The specific types and / or contents of the first diamine compound, the second diamine compound, the dianhydride compound, the dicarbonyl compound, the DMAc, the propylene oxide, the pyridine, and the acetic anhydride in Examples 2 to 9 are as shown in Table 1 below.

[0217] <Comparative Examples 1 to 6> Polymer resins of Comparative Examples 1 to 6 were prepared in the same manner as in Example 1, except that the type and / or content of the first diamine compound, the type and / or content of the second diamine compound, the content of the dianhydride compound, the type and / or content of the dicarbonyl compound, and the contents of DMAc, propylene oxide, pyridine, and acetic anhydride were changed. Then, polymer resin solutions and optical films of Comparative Examples 1 to 6 were prepared in the same manner as in Example 1.

[0218] The specific types and / or contents of the first diamine compound, the second diamine compound, the dianhydride compound, the dicarbonyl compound, and the DMAc, propylene oxide, pyridine, and acetic anhydride contents of Comparative Examples 1 to 6 are as shown in Table 1 below.

[0219] [Table 1] JPEG0007811650000019.jpg14170

[0220] <Measurement example> The polymer resins and optical films produced in the examples and comparative examples were subjected to the following measurements.

[0221] 1) pH of the second reaction solution and the polymer resin solution: The prepared solution (second reaction solution or polymer resin solution) was diluted with DMAc to the same concentration (wt%). To enable relative comparison of the pH of organic solutions, the concentrations (wt%) must be the same. In this invention, all pH measurement solutions were prepared and measured based on 12 wt%.

[0222] Measurement equipment: Analysis was performed using an InLab Power Pro-ISM sensor installed on a Mettler Toledo pH meter (model name: Seven compact S220).

[0223] Measurement method: Before measuring the pH of the solution, a pH 7 standard solution (black reagent) was measured first to stabilize the equipment. The pH of the standard solution was measured at least three times to confirm that it was 7.0 ± 0.2. Once the equipment stabilized, sample measurement began.

[0224] The solutions (second reaction solutions or polymer resin solutions) prepared in the Examples and Comparative Examples were diluted to 12 wt% with DMAc. 15 ml of the prepared solutions were divided into vials to prepare measurement samples. The measurement samples were kept at room temperature (25±2°C), and a pH sensor was immersed in the measurement samples at that temperature to measure. Each sample was measured five or more times, and the most frequent value was used as the pH value of the solution.

[0225] Between measurements of each sample, the sensor surface was washed with distilled water, wiped with soft wipe-all, and thoroughly dried before use.

[0226] 2) Number average molecular weight of polymer resin: The number average molecular weight and molecular weight distribution were measured using GPC (standard polystyrene, solvent THF).

[0227] The specific analytical equipment, analytical conditions, and sample preparation methods used are as follows:

[0228] 1.Analysis Equipment GPC Waters Set -Module: Waters Alliance e2695 -Detector: Waters 2414 Refractive index Detector

[0229] 2.Analysis conditions: -Columns: Agilent PLgel 5um Mixed C*2 (with 1 guard column) -Mobile Phase: 10mM LiBr in DMAc -Column and Detector Temperature: 50℃ -Injection Volume: 20ul -Flow Rate: 1.0ml / min

[0230] 3. Sample Preparation -Solid Contents 0.25 (w / w)% in DMAc -Fully dissolved samples were filtered with a 0.45 μm pore sized PTFE syringe filter.

[0231] 3) Chlorine (Cl) content (ppm): The chlorine (Cl) content of the optical films prepared in the examples and comparative examples was measured as follows.

[0232] Measurement equipment: The analysis was performed using a Dionex ICS-2000 Ion Chromatography System, an ion chromatograph equipped with two columns [IonPac AS18 Analytical (4x250mm) + AG18 Guard (4x50mm)] and an eluent [Dionex EGC-KOH III Cartridge].

[0233] Measurement Method: 50 μm-thick optical films prepared in the Examples and Comparative Examples were cut into approximately 0.5 cm x 0.5 cm pieces, freeze-dried, and pulverized to produce optical film powder. The powdered optical film was then mixed with distilled water at a ratio of 5 wt% and chlorine (Cl), specifically chloride ions (Cl-), were extracted from the optical film. Specifically, 0.2 g of optical film powder and 3.8 g of water were placed in a 20 mL vial and subjected to ultrasonic extraction using a Branson 5510 ultrasonic bath for 2 hours. This resulted in a chloride extraction mixture containing the chloride (Cl) extracted from the optical film. The resulting chloride extraction mixture was filtered through a 0.45 μm nylon filter to prepare a measurement sample. 20 μL of the measurement sample was placed in an ion chromatograph set at a column temperature of 30°C and a measurement cell temperature of 35°C, and the area of ​​the separated ion peaks corresponding to chloride ions was measured. To calculate the chloride ion content, Thermo Scientific's Dionex Seven Anion Standard was diluted with distilled water to prepare chloride ion standard solutions in the concentration range of 0.04 ppm to 1 ppm (0.04 ppm, 0.06 ppm, 0.08 ppm, 0.1 ppm, 1.0 ppm). These were then analyzed by ion chromatography using the same method as the measurement samples. The peak area corresponding to the chloride ion measured using the standard solution was confirmed, and a calibration curve was created.

[0234] The calibration curve can be expressed as a linear function as shown in Equation 1 below.

[0235] <Expression 1> y = ax + b

[0236] In Equation 1, y is the peak area, x is the concentration of the standard solution, a is the slope of the calibration curve, and b is the y-axis intercept of the calibration curve. The calibration curve obtained by Equation 3 can be applied to the peak area (y) of the measurement sample to calculate the chlorine concentration (x) of the measurement sample. The chlorine concentration (x) of the measurement sample can be calculated using Equation 2 below.

[0237] <Expression 2> x = (yb) / a

[0238] Next, the chlorine content in the optical film is calculated taking into account the dilution ratio applied to the measurement sample production. Specifically, the weight ratio of the optical film applied to the measurement sample can be calculated using the following Equation 3.

[0239] <Expression 3> Weight ratio of optical film in measurement sample=(weight of optical film) / (weight of optical film+weight of distilled water)

[0240] In Equation 3, the "weight of the optical film" means the weight of the optical film used in producing the measurement sample.

[0241] Next, the chlorine concentration of the optical film is calculated by the following formula 4 using the weight ratio of the optical film in the measurement sample and the chlorine concentration of the measurement sample.

[0242] <Expression 4> Chlorine concentration of optical film=(chlorine concentration of measurement sample) / (weight ratio of optical film in measurement sample)

[0243] 4) Yellowness index (YI): Yellowness index was measured using a spectrophotometer (CM-3700D, KONICA MINOLTA) according to the standard ASTM E313.

[0244] 5) Light transmittance (%): According to the standard ASTM E313, the average light transmittance at wavelengths of 360 to 740 nm was measured using a spectrophotometer (CM-3700D, KONICA MINOLTA).

[0245] The measurement results are shown in Table 2 below.

[0246] [Table 2]

[0247] As shown in the measurement results in Table 1, the examples of the present invention have a second reaction solution with a pH of 8 or more, a polymer resin solution with a pH of 6 to 7, a resin with a number average molecular weight of 150,000 or more, an excellent degree of polymerization, and excellent yellowing resistance and light transmittance.

[0248] However, in Comparative Example 1, the pH of the second reaction solution was less than 8, the number-average molecular weight of the resin was less than 150,000, and it was found that the polymerization reaction was insufficient. Furthermore, the yellowing degree was high and the light transmittance was low, confirming poor visibility. In Comparative Example 2, the number-average molecular weight was 205,400, and the degree of polymerization was excellent, but the proportion of dianhydride-based compounds was high, confirming poor yellowing and poor visibility. In Comparative Example 3, the amount of propylene oxide added was approximately 3.5 times the TPC content on a molar basis. However, the pH of the second reaction solution was less than 8, and the number-average molecular weight of the resin was less than 150,000, confirming poor polymerization. Furthermore, the yellowing degree was high and the light transmittance was low, confirming poor visibility. In Comparative Example 4, the amount of propylene oxide added was about 7.5 times the TPC content on a molar basis, the pH of the second reaction solution exceeded 9, and the resin had a number average molecular weight of 189,634, showing an excellent degree of polymerization. However, visibility was poor due to high yellowness. In Comparative Example 5, a dianhydride compound was not added, and a dicarbonyl compound was polymerized with a first diamine compound and a second diamine compound. Visibility was poor due to high yellowness and low light transmittance. In Comparative Example 6, propylene oxide was added in an amount approximately 2.25 times the molar amount of TPC, and pyridine and acetic anhydride were added in an amount approximately 1.1 times the molar amount of 6FDA. The pH of the second reaction solution was less than 8, the pH of the polymer resin solution was less than 6.0, and the number average molecular weight of the resin was less than 150,000, indicating that the polymerization reaction had not proceeded sufficiently. Furthermore, the yellowness was high and the light transmittance was low, confirming poor visibility. [Explanation of symbols]

[0249] 100: Optical film 200:Display device 501: Display panel

Claims

1. a polymeric resin comprising imide repeat units and amide repeat units, the amide repeating units are contained in a ratio of 80 mol % or more relative to the imide repeating units and the amide repeating units, the imide repeat unit comprises a first repeat unit and a second repeat unit; the amide repeat unit comprises a third repeat unit and a fourth repeat unit; the first repeating unit is an imide repeating unit obtained by a polymerization reaction between a first diamine compound and a dianhydride compound; the second repeating unit is an imide repeating unit obtained by a polymerization reaction between a second diamine compound and the dianhydride compound, the third repeating unit is an amide repeating unit obtained by a polymerization reaction between a first diamine compound and a dicarbonyl compound, the fourth repeating unit is an amide repeating unit obtained by a polymerization reaction between a second diamine compound and the dicarbonyl compound; the first diamine compound is an aromatic diamine compound, the second diamine compound is an aliphatic diamine compound, With respect to 100 mole parts of the total content of the first diamine compound and the second diamine compound, The content of the first diamine compound is 85 to 95 parts by mole, The content of the second diamine compound is 5 to 15 mole parts. Optical film.

2. Contains 120 ppm (0.012% by weight) or less of chlorine (Cl), The optical film according to claim 1: Here, the chlorine concentration is measured by freeze-drying and powdering the optical film, extracting it with distilled water, and then subjecting the chlorine (Cl) extract to ion chromatography analysis.

3. Contains 50 ppm (0.005% by weight) or less of chlorine (Cl), 2. The optical film according to claim 1.

4. The first diamine compound is selected from the group consisting of bistrifluoromethylbenzidine (2,2'-bis(trifluoromethyl)benzidine, TFDB), 2,2-bis(4-(4-aminophenoxy)phenyl)hexafluoropropane (HFBAPP), bis(4-(4-aminophenoxy)phenyl)sulfone (BAPS), bis(4-(3-aminophenoxy)phenyl)sulfone (BAPSM), 4,4'-diaminodiphenylsulfone (4DDS), 3,3'-diaminodiphenylsulfone (3DDS), p-phenylenediamine (para-phenylene diamine, pPDA), m-phenylenediamine (metaphenylene diamine, mPDA), p-methylenedianiline (para-Methylene Dianiline, pMDA), m-methylenedianiline (meta-Methylene Dianiline, mMDA), 2,2-bis(4-(4-aminophenoxy)phenylpropane (BAPP), 4,4'-diaminodiphenylpropane (6HDA), 1,3-bis(4-aminophenoxy)benzene (134APB), 1,3-bis(3-aminophenoxy)benzene (133APB), 1,4-bis(4-aminophenoxy)biphenyl (BAPB), 4,4'-bis(4-amino-2-trifluoromethylphenoxy)biphenyl (6FAPBP), 3,3-diamino the compound (A) contains one or more compounds selected from the group consisting of 4,4-dihydroxydiphenyl sulfone (DABS), 2,2-bis(3-amino-4-hydroxyphenyl)propane (BAP), 4,4'-diaminodiphenylmethane (DDM), 4,4'-oxydianiline (4-ODA), 3,3'-oxydianiline (3-ODA), 2,2'-dimethyl-4,4'-(9-fluorenylidene)dianiline (MFDA), 9,9-bis(4-aminophenyl)fluorene (FDA), and 9,9-bis(3-fluoro-4-aminophenyl)fluorene (FFDA), The optical film according to claim 1 .

5. The second diamine compound comprises one or more compounds selected from the group consisting of 4,4'-methylenebiscyclohexylamine (MBCA), 1,3-bis(aminomethyl)cyclohexane, 1,4-cyclohexanediamine, bicyclo[2.2.1]heptanebis(methylamine), and cis, trans, and mixture isomers of the compounds. The optical film according to claim 1 .

6. The dianhydride compounds include 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride (6FDA), 4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic anhydride (TDA), pyromellic acid dianhydride (1,2,4,5-benzene tetracarboxylic dianhydride, pyromellictic acid dianhydride, PMDA), benzophenone tetracarboxylic dianhydride (3,3,4,4-benzophenone tetracarboxylic dianhydride, BTDA), biphenyltetracarboxylic dianhydride (3,3,4,4-biphenyltetracarboxylic dianhydride, BPDA), oxydiphthalic dianhydride (4,4-oxydiphthalic dianhydride, the compound (I) containing at least one selected from the group consisting of bis(3,4dicarboxyphenyl)dimethylsilane dianhydride (SiDA), bis(3,4dicarboxyphenyl)dimethylsilane dianhydride (BDSDA), sulfonyldiphthalic anhydride (SO2DPA), cyclobutane-1,2,3,4-tetracarboxylic dianhydride (CBDA), and 4,4'-(4,4'-Isopropylidenediphenoxy)bis(phthalic anhydride, 6HBDA); The optical film according to claim 1 .

7. The dicarbonyl compound includes at least one selected from the group consisting of phthaloyl chloride, terephthaloyl chloride (TPC), isophthaloyl chloride (IPC), 4,4'-biphenyldicarbonyl chloride (DPDOC), 4,4'-oxybis(benzoyl chloride) (OBBOC), and naphthalene-2,3-dicarbonyl dichloride; The optical film according to claim 1 .

8. having a yellowness index of 4.0 or less; 2. The optical film according to claim 1.

9. Light transmittance of 88.50% or more 2. The optical film according to claim 1.

10. a display panel; and The optical film according to any one of claims 1 to 9, disposed on the display panel; A display device comprising:

11. forming a first reaction solution using at least one of a first diamine compound and a second diamine compound, a dianhydride compound, a dicarbonyl compound, and a chlorine (Cl) acceptor; adding a dehydrating agent and an imidization catalyst to the first reaction solution and reacting them to form a second reaction solution; treating the second reaction solution to produce a solid-state polymer resin; dissolving the solid polymer resin to prepare a polymer resin solution; and casting the polymer resin solution; The content of the chlorine (Cl) acceptor is 4 to 7 times the content of the dicarbonyl compound in terms of moles, With respect to 100 mole parts of the total content of the first diamine compound and the second diamine compound, The content of the dicarbonyl compound is 80 to 99 parts by mole, The content of the dianhydride compound is 1 to 20 molar parts; A method for manufacturing an optical film.

12. The first diamine compound is an aromatic diamine compound, and the second diamine compound is an aliphatic diamine compound. The method for producing an optical film according to claim 11 .

13. With respect to 100 mole parts of the total content of the first diamine compound and the second diamine compound, The content of the first diamine compound is 85 to 95 parts by mole, The content of the second diamine compound is 5 to 15 mole parts. The method for producing an optical film according to claim 11 .

14. The chlorine (Cl) acceptor includes a cyclic ether compound. The method for producing an optical film according to claim 11 .

15. The cyclic ether-based compound includes at least one of an epoxide-based compound, an oxetane-based compound, a tetrahydrofuran-based compound, and a tetrahydropyran-based compound. The method for producing the optical film according to claim 14 .

16. The cyclic ether-based compound includes a propylene oxide-based compound. The method for producing the optical film according to claim 14 .

17. The pH of the second reaction solution is 8 to 9. The method for producing an optical film according to claim 11 .

18. The pH of the polymer resin solution is 6 to 7. The method for producing an optical film according to claim 11 .

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