Photosensitive resin composition, photoresist containing the same, display device containing the same, and low-temperature curing method for photosensitive resin composition

Abstract

The present disclosure relates to a photosensitive resin composition, a photoresist, a display device, and a method for curing the photosensitive resin composition at a low temperature.

Description

Technical Field

[0001] The present disclosure relates to a photosensitive resin composition, a photoresist, a display device, and a method for curing the photosensitive resin composition at a low temperature.

[0002] CROSS-REFERENCE TO RELATED APPLICATIONS

[0003] This application claims priority based on Korean Patent Application No. 10-2021-0059775, filed on May 10, 2021, which is hereby incorporated by reference in its entirety. Background Art

[0004] Recently, organic light emitting diode (OLED) displays have been widely used, and upper touch panels have also been widely used from the add-on method in the form of a film to the on-cell method. In the case of the on-cell method touch screen panel, since it is directly manufactured on top of the panel after the OLED panel is completed, a low-temperature curing process (less than 100°C) is essential so as not to affect the life of the OLED device.

[0005] For the above reasons, in the case of an insulating film material used between electrodes or on the upper portion of electrodes in a touch screen panel of an on-cell method that has been applied to the upper portion of an OLED, low-temperature curing characteristics should be achieved.

[0006] To achieve low-temperature curing properties, post-curing is typically performed by applying a subsequent ultraviolet (UV) curing process in addition to the ultraviolet (UV) process conditions used for patterning, but most of these materials lack processability (two-step UV process) and chemical resistance.

[0007] Prior art literature

[0008] Patent Literature

[0009] (Patent Document 1) Korean Patent Publication No. 10-2012-0022616 Summary of the Invention

[0010] Technical issues

[0011] An object of the present disclosure is to provide a photosensitive resin composition, a photoresist, and a display including the same.

[0012] Another object of the present disclosure is to provide a low-temperature curing method using the photosensitive resin composition.

[0013] Technical Solution

[0014] One embodiment of the present disclosure provides a photosensitive resin composition including a binder resin and a compound represented by the following Chemical Formula 1,

[0015] [Chemical Formula 1]

[0016]

[0017] In Chemical Formula 1,

[0018] A1 is -OH; -SH; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted amino group,

[0019] “-” means the site of connection with Chemical Formula 1,

[0020] A2 and A3 are the same as or different from each other and are each independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group,

[0021] x is an integer from 20 to 50, and

[0022] The binder resin includes a polymer including repeating units of the following Chemical Formulas 3-1 to 3-4.

[0023] [Chemical Formula 3-1]

[0024]

[0025] [Chemical Formula 3-2]

[0026]

[0027] [Chemical Formula 3-3]

[0028]

[0029] [Chemical formula 3-4]

[0030]

[0031] In Chemical Formulas 3-1 to 3-4,

[0032] Ar is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0033] L101 and L102 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group,

[0034] R101 and R102 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group,

[0035] T is a substituted or unsubstituted aliphatic hydrocarbon ring,

[0036] a to d are each 0 or more and 1 or less as a mole fraction, and 0 <a+b+c+d≤1,

[0037] r101 is an integer of 1 to 3, and when r101 is 2 or greater, R101 are the same as or different from each other,

[0038] r102 is an integer of 1 or greater, and when r102 is 2 or greater, R102 are the same as or different from each other, and

[0039] It refers to the site of attachment to another moiety.

[0040] One embodiment of the present disclosure provides a photoresist prepared using the photosensitive resin composition or the cured product.

[0041] One embodiment of the present disclosure provides a display device including the photoresist.

[0042] One embodiment of the present disclosure provides a low-temperature curing method for a photosensitive resin composition, comprising the following steps:

[0043] (a) coating the photosensitive resin composition on a substrate;

[0044] (b) drying or prebaking the coated substrate;

[0045] (c) exposing the dried or prebaked substrate to light;

[0046] (d) forming a pattern; and

[0047] (e) The substrate is post-baked at a temperature within a range of 50°C or higher and lower than 100°C.

[0048] Beneficial effects

[0049] The photosensitive resin composition according to one embodiment of the present disclosure has excellent solubility in a solvent, and has excellent heat resistance and chemical resistance.

[0050] The photosensitive resin composition according to one embodiment of the present specification has excellent pattern characteristics when forming an organic film.

[0051] The photosensitive resin composition according to one embodiment of the present specification has excellent chemical resistance by being easily cured even at a low temperature below 100°C. BRIEF DESCRIPTION OF THE DRAWINGS

[0052] Figure 1 Shown are the results of GPC measurement of a binder resin according to one embodiment of the present disclosure.

[0053] Figure 2 The mask holes of the microvia according to Example 1, which is one embodiment of the present disclosure, are shown.

[0054] Figure 3 Shown are minimum pore pattern characteristics of the micropores according to Example 1, which is one embodiment of the present disclosure.

[0055] Figure 4 The mask holes of the microvia according to Comparative Example 1 are shown.

[0056] Figure 5 The minimum hole pattern characteristics of the micropores according to Comparative Example 1 are shown. DETAILED DESCRIPTION

[0057] Hereinafter, the present disclosure will be described in detail.

[0058] One embodiment of the present disclosure provides a photosensitive resin composition including a binder resin and a compound represented by the following Chemical Formula 1.

[0059] [Chemical Formula 1]

[0060]

[0061] In Chemical Formula 1,

[0062] A1 is -OH; -SH; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted amino group,

[0063] “-” means the site of connection with Chemical Formula 1,

[0064] A2 and A3 are the same as or different from each other and are each independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group, and

[0065] x is an integer from 20 to 50.

[0066] The binder resin includes a polymer including repeating units of the following Chemical Formulas 3-1 to 3-4.

[0067] [Chemical Formula 3-1]

[0068]

[0069] [Chemical Formula 3-2]

[0070]

[0071] [Chemical Formula 3-3]

[0072]

[0073] [Chemical formula 3-4]

[0074]

[0075] In Chemical Formulas 3-1 to 3-4,

[0076] Ar is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0077] L101 and L102 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group,

[0078] R101 and R102 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group,

[0079] T is a substituted or unsubstituted aliphatic hydrocarbon ring,

[0080] a to d are each 0 or more and 1 or less as a mole fraction, and 0 <a+b+c+d≤1,

[0081] r101 is an integer of 1 to 3, and when r101 is 2 or greater, R101 are the same as or different from each other,

[0082] r102 is an integer of 1 or greater, and when r102 is 2 or greater, R102 are the same as or different from each other, and

[0083] It refers to the site of attachment to another moiety.

[0084] The photosensitive resin composition according to one embodiment of the present disclosure includes an epoxy-containing polymer as a binder resin. The epoxy group contained in the binder resin enables thermal curing. In addition, the binder resin according to one embodiment of the present disclosure includes an acid group (e.g., a carboxyl group) and thus has excellent developability by improving pattern characteristics.

[0085] The photosensitive resin composition according to one embodiment of the present disclosure includes a compound represented by the above chemical formula 1. According to one embodiment of the present disclosure, the compound represented by the above chemical formula 1 is used as a curing accelerator. Specifically, the compound represented by the above chemical formula 1 is capable of both ultraviolet (UV) curing and thermal curing, so that it is included in the composition to have excellent chemical resistance and can form an ultrafine pattern. In addition, the compound represented by the above chemical formula 1 has the advantage of being able to cure the photosensitive resin composition even at a low temperature of less than 100°C or with a small exposure dose.

[0086] In the present disclosure, if a specified part “includes” specified elements, unless there is any specific contrary description, this means that additional elements may be further included rather than excluding other elements.

[0087] In the present disclosure, "layer" is used interchangeably with "film" as is commonly used in the art, and refers to a coating covering a desired area. The size of a "layer" is not limited, and each "layer" may be the same or different in size. According to one embodiment, the size of a "layer" may be equal to the size of the entire device, may correspond to the size of a specific functional area, and may be as small as a single sub-pixel.

[0088] Unless otherwise limited in the present disclosure, all technical terms and scientific terms used in the present disclosure all have those identical meanings that are generally understood by those of ordinary skill in the art to which the present disclosure belongs. Although methods and materials similar or equivalent to the methods and materials described in the present disclosure can be used to put into practice or test the embodiments of the present disclosure, suitable methods and materials will be described subsequently. All publications, patent applications, patents and other references mentioned in the present disclosure are incorporated into the present disclosure by reference in their entirety, and in the case of conflict, unless specific paragraphs are mentioned, otherwise the present disclosure (including definitions) shall prevail. In addition, materials, methods and examples are only illustrative and are not intended to limit.

[0089] In the present disclosure, the term "combination thereof" included in a Markush-type expression means a mixture or combination selected from one or more of the elements described in the Markush-type expression, and means including one or more selected from the elements.

[0090] In this disclosure, “-” and Refers to the site of attachment.

[0091] Examples of the substituent in the present disclosure are described below, but the present disclosure is not limited thereto.

[0092] In the present disclosure, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed into another substituent, and the position to be substituted is not limited as long as the position is a position where a hydrogen atom is substituted (i.e., a position where a substituent can be substituted), and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0093] In the present disclosure, the term "substituted or unsubstituted" means that it is substituted with one or more substituents selected from the group consisting of hydrogen; deuterium; alkyl; alkenyl; cycloalkyl; aryl; heterocyclic group; amino group; and curable group, substituted with a substituent in which two or more of the substituents exemplified above are linked, or has no substituent.

[0094] In the present disclosure, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but the alkyl group may have 1 to 20 carbon atoms. According to another embodiment, the alkyl group may have 1 to 10 carbon atoms. Specific examples of the alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, etc., but the present disclosure is not limited thereto.

[0095] In the present disclosure, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30; 2 to 20; 2 to 10; or 2 to 5. Specific examples of the alkenyl group may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, and the like, but the present disclosure is not limited thereto.

[0096] In the present disclosure, the cycloalkyl group is not particularly limited, but may have 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group may have 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group may have 3 to 20 carbon atoms. Specific examples of the cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., but the present disclosure is not limited thereto.

[0097] In the present disclosure, the aryl group is not particularly limited, but may have 6 to 60 carbon atoms and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group may have 6 to 30 carbon atoms. According to one embodiment, the aryl group may have 6 to 20 carbon atoms. As a monocyclic aryl group, the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but the present disclosure is not limited thereto. As a polycyclic aryl group, the aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylene group, a triphenylene group, but the present disclosure is not limited thereto.

[0098] In the present disclosure, the heterocyclic group is an aromatic ring group containing one or more of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but the heterocyclic group may have 2 to 60 carbon atoms. According to one embodiment, the heterocyclic group may have 2 to 30 carbon atoms. Examples of heterocyclic groups may include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl and the like, but the present disclosure is not limited thereto.

[0099] In this disclosure, an amine group refers to -NR amin1 R amin2 , and R amin1 and R amin2 The groups may be the same as or different from each other and may each independently be an alkyl group, an aryl group, or a deuterated analog thereof.

[0100] In the present disclosure, the above description of the alkyl group applies, except that the alkylene group is divalent.

[0101] In the present disclosure, the above description of the aryl group applies except that the arylene group is divalent.

[0102] In the present disclosure, an "adjacent" group may refer to a substituent that is substituted on an atom directly connected to the atom substituted by the corresponding substituent, a substituent that is spatially closest to the corresponding substituent, or another substituent that is substituted on the atom substituted by the corresponding substituent. For example, two substituents substituted at the ortho positions in a phenyl ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as groups that are "adjacent" to each other.

[0103] In the present disclosure, a "curable group" may refer to a group capable of causing crosslinking by heat treatment and / or exposure to light, or a reactive substituent for crosslinking between compounds, etc. Crosslinking can be generated simultaneously with the connection of free radicals generated when decomposing carbon-carbon multiple bonds or cyclic structures by heat treatment or light irradiation.

[0104] In the present disclosure, a free radical compound refers to a compound having unpaired electrons. In addition, a free radical compound means a compound having unpaired electrons, and depending on the type of compound, there may be compounds that are both cations and free radicals. For reference, a cationic compound in the present disclosure means a compound having a positive net charge due to a greater number of protons than electrons. Generally, it is known that π-radical compounds are unstable, but when they have an appropriate structure such as a π-conjugated system, an alkyl substituent, etc., cationic free radical materials can exist stably. (Org. Biomol. Chem., 2005, 3, 561-569)

[0105] According to one embodiment of the present disclosure, the curable group may be selected from the following structures.

[0106]

[0107] In the structure,

[0108] L11 is a direct bond; -O-; -S-; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

[0109] lk is 1 or 2,

[0110] When lk is 2, L11 are the same as or different from each other, and

[0111] R21 is a substituted or unsubstituted alkyl group.

[0112] According to one embodiment of the present disclosure, L11 is a direct bond; a methylene group; or an ethylene group.

[0113] According to another embodiment, L11 is a direct bond.

[0114] According to one embodiment of the present disclosure, R21 is methyl; or ethyl.

[0115] According to another embodiment, R21 is methyl.

[0116] In this disclosure, mole fraction means the ratio of the number of moles of a given component to the total number of moles of all components.

[0117] In the present disclosure, "monomer" means a unit compound that can be converted into a polymer compound through a polymerization reaction, and "monomer unit" is intended to mean a repeating unit within a polymer or copolymer. Specifically, this means that in a state where the corresponding compound is polymerized and bonded to the inside of the polymer, all or part of two or more substituents are removed from the structure of the corresponding compound, and a free radical for bonding to other units of the polymer is located at that position.

[0118] In this disclosure, "polymer" means a polymer composition prepared by polymerizing monomers, whether the monomers are of the same or different types. Thus, the general term "polymer" generally includes "homopolymer," which refers to a polymer prepared from one type of monomer, and "copolymer," which refers to a polymer prepared from two or more different types of monomers.

[0119] In this disclosure, "copolymer" encompasses polymers prepared from two different types of monomers and polymers prepared from more than two different types of monomers.

[0120] In the present disclosure, solid components refer to components other than the solvent in the resin composition. Solid content and the basis of weight parts based on the solid content of each component can be measured by general analytical means used in the art, such as liquid chromatography, gas chromatography, etc.

[0121] According to one embodiment of the present disclosure, the binder resin includes a polymer including: a first unit represented by the following Chemical Formula 3-1; a second unit represented by the following Chemical Formula 3-2; a third unit represented by the following Chemical Formula 3-3; and a fourth unit represented by the following Chemical Formula 3-4.

[0122] [Chemical Formula 3-1]

[0123]

[0124] [Chemical Formula 3-2]

[0125]

[0126] [Chemical Formula 3-3]

[0127]

[0128] [Chemical formula 3-4]

[0129]

[0130] In Chemical Formulas 3-1 to 3-4,

[0131] According to one embodiment of the present disclosure, the binder resin may include a state in which the above chemical formulas 3-1 to 3-4 are repeatedly combined in any order. In other words, the repeating units of the above chemical formulas 3-1 to 3-4 in the binder resin according to one embodiment of the present disclosure may be continuously combined or may be discontinuously combined.

[0132] According to one embodiment of the present disclosure, Ar is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclyl group.

[0133] According to one embodiment of the present disclosure, Ar is a substituted or unsubstituted C6 to C 30 Aryl; or substituted or unsubstituted C2 to C 30 Heterocyclic group.

[0134] According to one embodiment of the present disclosure, Ar is a substituted or unsubstituted C6 to C 20 Aryl; or substituted or unsubstituted C2 to C 20 Heterocyclic group.

[0135] According to one embodiment of the present disclosure, Ar is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted fluorenyl group.

[0136] According to one embodiment of the present disclosure, Ar is phenyl.

[0137] According to one embodiment of the present disclosure, L101 and L102 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group.

[0138] According to one embodiment of the present disclosure, L101 and L102 are the same as or different from each other and are each independently a direct bond; substituted or unsubstituted C1 to C 10 Alkylene; or substituted or unsubstituted C6 to C 30 Arylene.

[0139] According to one embodiment of the present disclosure, L101 and L102 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted C1 to C5 alkylene; or a substituted or unsubstituted C6 to C 20 Arylene.

[0140] According to one embodiment of the present disclosure, L101 and L102 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted methylene group; a substituted or unsubstituted ethylene group; a substituted or unsubstituted propylene group; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

[0141] According to one embodiment of the present disclosure, L101 and L102 are the same as or different from each other, and are each independently a direct bond; a methylene group; or an ethylene group.

[0142] According to one embodiment of the present disclosure, L101 is methylene.

[0143] According to one embodiment of the present disclosure, L102 is a methylene group.

[0144] According to one embodiment of the present disclosure, L101 and L102 are methylene groups.

[0145] According to one embodiment of the present disclosure, R101 and R102 are the same as or different from each other, and each independently is hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group.

[0146] According to one embodiment of the present disclosure, R101 and R102 are the same as or different from each other, and each independently is hydrogen; deuterium; substituted or unsubstituted C1 to C 10 alkyl; substituted or unsubstituted C2 to C 10 alkenyl; substituted or unsubstituted C6 to C 30 aryl; or substituted or unsubstituted C2 to C 30 heterocyclic group.

[0147] According to one embodiment of the present disclosure, R101 is hydrogen.

[0148] According to one embodiment of the present disclosure, R102 is hydrogen.

[0149] According to one embodiment of the present disclosure, R101 and R102 are hydrogen.

[0150] According to one embodiment of the present disclosure, T is a substituted or unsubstituted aliphatic hydrocarbon ring.

[0151] According to one embodiment of the present disclosure, T is a substituted or unsubstituted C3 to C 10 aliphatic hydrocarbon ring.

[0152] According to one embodiment of the present disclosure, T is a cyclohexane ring.

[0153] According to one embodiment of the present disclosure, a is a mole fraction of 0 < a < 1, b is a mole fraction of 0 < b < 1, c is a mole fraction of 0 < c < 1, d is a mole fraction of 0 < d < 1, and a + b + c + d ≤ 1.

[0154] The mole fractions a, b, c, and d refer to the values obtained by dividing the number of unit repeats by the total number of unit repeats. That is, a is the value obtained by dividing the number of unit repeats of Chemical Formula 3-1 by the total number of units in the copolymer, b is the value obtained by dividing the number of unit repeats of Chemical Formula 3-2 by the total number of units in the copolymer, c is the value obtained by dividing the number of unit repeats of Chemical Formula 3-3 by the total number of units in the copolymer, and d is the value obtained by dividing the number of unit repeats of Chemical Formula 3-4 by the total number of units in the copolymer. Furthermore, the mole fraction does not indicate the order or number of repeats.

[0155] According to one embodiment of the present disclosure, a is a mole fraction and is greater than 0 and less than 1, preferably 0.1 to 0.6; or 0.3 to 0.4. When a is within the above range, suitable film strength characteristics are achieved. In particular, when a is 0.3 or greater, film strength is excellent, and when a is 0.4 or less, pattern characteristics are excellent.

[0156] According to one embodiment of the present disclosure, b is a mole fraction and is greater than 0 and less than 1, preferably 0.01 to 0.5; or 0.1 to 0.2. When b is within the above range, desired micropattern characteristics can be achieved. In particular, when b is 0.1 or greater, development characteristics are excellent, and when b is 0.2 or less, since overdevelopment does not occur, there is no concern about pattern peeling due to overdevelopment.

[0157] According to one embodiment of the present disclosure, c is a mole fraction and is greater than 0 and less than 1, preferably 0.1 to 0.6; or 0.2 to 0.4. When c is within the above range, desired thermosetting properties are achieved. In particular, when c is 0.2 or greater, thermosetting properties are excellent, and when c is 0.4 or less, micropatterning is facilitated.

[0158] According to one embodiment of the present disclosure, d is a mole fraction and is greater than 0 and less than 1, preferably 0.01 to 0.5; or 0.1 to 0.3. When d is within the above range, thermosetting properties (especially chemical resistance) are achieved. In particular, when d is 0.1 or greater, chemical resistance is excellent, and when d is 0.3 or less, it is advantageous to achieve micropatterning by thermal curing.

[0159] According to one embodiment of the present disclosure, a+b+c+d is 1.

[0160] According to a preferred embodiment of the present disclosure, a=0.3, b=0.2, c=0.4, and d=0.1.

[0161] According to one embodiment of the present disclosure, r101 is an integer of 1 to 3, and when r101 is 2 or greater, R101 are the same as or different from each other.

[0162] According to one embodiment of the present disclosure, r101 is 3.

[0163] According to one embodiment of the present disclosure, r102 is an integer of 1 or greater, and when r102 is 2 or greater, R102 are the same as or different from each other.

[0164] According to one embodiment of the present disclosure, r102 is an integer from 1 to 11.

[0165] According to one embodiment of the present disclosure, r102 is 11.

[0166] According to one embodiment of the present disclosure, the binder resin includes a polymer containing an epoxy group. The epoxy group has thermosetting properties.

[0167] According to one embodiment of the present disclosure, the weight average molecular weight of the binder resin is 5,000 g / mol or more and 150,000 g / mol or less. According to a preferred embodiment of the present disclosure, the weight average molecular weight of the binder resin is 8,000 g / mol or more and 12,000 g / mol or less. When the weight average molecular weight of the binder resin is within the above range, the viscosity of the solution is easily controlled and phase separation from other components does not occur.

[0168] According to one embodiment of the present disclosure, the content of the binder resin is 5 to 30 parts by weight relative to 100 parts by weight of the photosensitive resin composition. Preferably, it is 5 to 15 parts by weight. When the content of the binder resin is 5 parts by weight or more, the polymer component is suitable for promoting the formation of a thin film, and when the content of the binder resin is 30 parts by weight or less, a thin film forming effect can be expected by injecting additives such as surfactants.

[0169] The weight average molecular weight can be measured by gel permeation chromatography (GPC). In the process of measuring the weight average molecular weight by the GPC method, a known analyzer, a detector such as a differential refractive index detector, and an analytical column can be used, and commonly used temperature conditions, solvents, solvent rates, etc. can be applied.

[0170] Furthermore, according to one embodiment of the present disclosure, as the binder resin including an epoxy group as a functional group, those generally used in the art may be used.

[0171] According to one embodiment of the present disclosure, the binder resin is a copolymer including one or more types of epoxy-containing monomers.

[0172] The epoxy group-containing monomer may include glycidyl methacrylate, 3,4-epoxybutyl methacrylate, 4,5-epoxyhexyl methacrylate, and 6,7-epoxypeptyl methacrylate, but the present disclosure is not limited thereto.

[0173] According to one embodiment of the present disclosure, the binder resin may be a copolymer polymerized from a binder resin composition including an epoxy-based monomer and a (meth)acrylate-based monomer.

[0174] Examples of epoxy compound-based monomers may include one or more compounds selected from the group consisting of oxetane methacrylate, allyl glycidyl ether, glycidyl methacrylate, 3,4-epoxycyclohexylmethyl methacrylate, 5-norbornene-2-methyl-2-carboxylic acid glycidyl ester (a mixture of endo and exo forms), 1,2-epoxy-5-hexene, and 1,2-epoxy-9-decene, but the present disclosure is not limited thereto.

[0175] Examples of the (meth)acrylate-based monomer may be selected from methacrylic acid, methacrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, dimethylaminoethyl methacrylate, isobutyl methacrylate, tert-butyl methacrylate, cyclohexyl methacrylate, isobornyl methacrylate, ethylhexyl methacrylate, 2-phenoxyethyl methacrylate, tetrahydrofurfuryl methacrylate, hydroxyethyl methacrylate, ethyl α-hydroxymethacrylate, propyl α-hydroxymethacrylate, and butyl α-hydroxymethacrylate, but the present disclosure is not limited thereto.

[0176] According to one embodiment of the present disclosure, A1 is -OH; -SH; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted amine group.

[0177] According to one embodiment of the present disclosure, A1 is -OH; -SH; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted amine group.

[0178] According to one embodiment of the present disclosure, A1 is -OH; -SH; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted amine group.

[0179] According to one embodiment of the present disclosure, A1 is -OH; -SH; substituted or unsubstituted C1 to C 10 an alkyl group; or a substituted or unsubstituted amino group.

[0180] According to one embodiment of the present disclosure, A2 and A3 are the same as or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0181] According to one embodiment of the present disclosure, A2 and A3 are the same as or different from each other and are each independently hydrogen; deuterium; or a substituted or unsubstituted C1 to C 10 alkyl.

[0182] According to one embodiment of the present disclosure, A2 and A3 are the same as or different from each other, and are each independently hydrogen; deuterium; or an alkyl group having 1 to 10 carbon atoms.

[0183] According to one embodiment of the present disclosure, A2 and A3 are the same as or different from each other, and are each independently an alkyl group having 1 to 10 carbon atoms.

[0184] According to one embodiment of the present disclosure, A2 and A3 are the same as or different from each other, and are each independently hydrogen; or a substituted or unsubstituted methyl group.

[0185] According to one embodiment of the present disclosure, A2 and A3 are the same as or different from each other, and are each independently hydrogen or methyl.

[0186] According to one embodiment of the present disclosure, A2 and A3 are the same as or different from each other, and are each independently a substituted or unsubstituted methyl group.

[0187] According to one embodiment of the present disclosure, A2 and A3 are methyl groups.

[0188] According to one embodiment of the present disclosure, the above Chemical Formula 1 is represented by the following Chemical Formula 11.

[0189] [Chemical Formula 11]

[0190]

[0191] In Chemical Formula 11, A1 and x are as defined in Chemical Formula 1 above.

[0192] According to one embodiment of the present disclosure, x is an integer from 20 to 50. According to one preferred embodiment of the present disclosure, x is an integer from 25 to 45.

[0193] According to one embodiment of the present disclosure, the above Chemical Formula 1 is represented by the following Chemical Formula 101.

[0194] [Chemical Formula 101]

[0195]

[0196] According to one embodiment of the present disclosure, the content of the compound represented by the above chemical formula 1 is 0.05 to 9 parts by weight relative to 100 parts by weight of the photosensitive resin composition. According to a preferred embodiment of the present disclosure, the content of the compound represented by the above chemical formula 1 is 0.1 to 9 parts by weight relative to the weight of the photosensitive resin composition. However, the present disclosure is not limited to the above example. When the compound represented by the chemical formula 1 of the present disclosure is included in the amount range, it has the advantages of being able to be cured at a low temperature below 100°C, and chemical resistance and hole pattern characteristics become excellent.

[0197] According to one embodiment of the present disclosure, the photosensitive resin composition further includes at least one of: a multifunctional monomer; a surfactant; and a photopolymerization initiator.

[0198] According to one embodiment of the present disclosure, the photosensitive resin composition further includes: a multifunctional monomer; a surfactant; and a photopolymerization initiator.

[0199] According to one embodiment of the present disclosure, the multifunctional monomer may be any one or more of the following: unsaturated carboxylic acid ester; aromatic vinyl; unsaturated ether; unsaturated imide; and acid anhydride, and may further include other multifunctional monomers known in the art.

[0200] According to one embodiment of the present disclosure, the content of the multifunctional monomer is 1 to 40 parts by weight, or 1 to 20 parts by weight, relative to 100 parts by weight of the photosensitive resin composition. As a preferred example, the content of the multifunctional monomer is 1 to 20 parts by weight, relative to 100 parts by weight of the photosensitive resin composition. However, the present disclosure is not limited to the above range.

[0201] Specific examples of unsaturated carboxylic acid esters can be selected from benzyl methacrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, dimethylaminoethyl methacrylate, isobutyl methacrylate, tert-butyl methacrylate, cyclohexyl methacrylate, isobornyl methacrylate, ethylhexyl methacrylate, 2-phenoxyethyl methacrylate, tetrahydrofurfuryl methacrylate, hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxy-3-chloropropyl methacrylate, 4-hydroxybutyl methacrylate, octyloxy-2-hydroxypropyl methacrylate, glyceryl methacrylate, 2-methoxyethyl methacrylate, 3-methoxybutyl methacrylate, ethyl methacrylate, The present invention also includes the following: 1,2-diethylene glycol methacrylate, methoxy triethylene glycol methacrylate, methoxy tripropylene glycol methacrylate, poly (ethylene glycol) methyl ether methacrylate, phenoxy diethylene glycol methacrylate, p-nonylphenoxy polyethylene glycol methacrylate, p-nonylphenoxy polypropylene glycol methacrylate, glycidyl methacrylate, tetrafluoropropyl methacrylate, 1,1,1,3,3,3-hexafluoroisopropyl methacrylate, octafluoropentyl methacrylate, heptadecafluorodecyl methacrylate, tribromophenyl methacrylate, methyl α-hydroxy methacrylate, ethyl α-hydroxy methacrylate, propyl α-hydroxy methacrylate and butyl α-hydroxy methacrylate, but the present disclosure is not limited thereto. In addition, those skilled in the art can also arbitrarily select other aromatic vinyls, unsaturated ethers, unsaturated imides and acid anhydrides from known substances.

[0202] Additional examples of the multifunctional monomer may include one or more of pentaerythritol tetramethacrylate, pentaerythritol trimethacrylate, dipentaerythritol pentamethacrylate, dipentaerythritol hexamethacrylate, dipentaerythritol hexaacrylate (DPHA), etc., but the present disclosure is not limited thereto.

[0203] The surfactant is a silicone-based surfactant or a fluorine-based surfactant, and specifically, the silicone-based surfactant may include BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307, BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-33 1, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK-354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390, etc., and the fluorine-based surfactant may include one or more compounds selected from the following: DaiNippon F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-4 of Ink&Chemicals (DIC) 46. F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F-48 6, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF, TF-1131, TF-1140, TF1132, TF1027SF, TF-1441, TF-1442, etc., but the disclosure is not limited thereto. According to a preferred embodiment of the present disclosure, a mixture of two or more compounds selected from the above-mentioned surfactants is preferably used.

[0204] According to one embodiment of the present disclosure, the content of the surfactant is 0.1 to 5 parts by weight relative to 100 parts by weight of the photosensitive resin composition. As another example, the content of the surfactant is 0.1 to 3 parts by weight relative to 100 parts by weight of the photosensitive resin composition. As a preferred example, the content of the surfactant is 0.1 to 1 part by weight relative to 100 parts by weight of the photosensitive resin composition. As a preferred example, the content of the surfactant is 0.2 to 0.4 parts by weight relative to 100 parts by weight of the photosensitive resin composition. However, the present disclosure is not limited to the above ranges.

[0205] According to one embodiment of the present disclosure, the photopolymerization initiator is a material that triggers crosslinking by generating free radicals via light, and includes a mixture of one or more compounds selected from acetophenone-based compounds, biimidazole-based compounds, triazine-based compounds, and oxime-based compounds. According to one embodiment of the present disclosure, examples of photopolymerization initiators may include PBG-304, PBG-305, and PBG-309 from Trolly; and IRGACURE 651, IRGACURE 184, DAROCURE 1173, IRGACURE 2959, IRGACURE 127, IRGACURE 907, IRGACURE 369, IRGACURE 379EG, LUCIRIN TPO, IRGACURE 819, IRGACURE 784, and the like from BASF, but the present disclosure is not limited to the examples. According to a preferred embodiment of the present disclosure, a mixture of two or more compounds selected from the above-mentioned photopolymerization initiators is preferably used.

[0206] According to one embodiment of the present disclosure, the content of the photopolymerization initiator is 1 to 10 parts by weight relative to 100 parts by weight of the photosensitive resin composition. As a preferred example, the content of the photopolymerization initiator is 2 to 6 parts by weight relative to 100 parts by weight of the photosensitive resin composition. As a more preferred example, the content of the photopolymerization initiator is 2 to 4 parts by weight relative to 100 parts by weight of the photosensitive resin composition. However, the present disclosure is not limited to the above range.

[0207] According to one embodiment of the present disclosure, the photosensitive resin composition may further include other additives, such as a cross-linking agent, a silane coupling agent, etc., but the present disclosure is not limited thereto.

[0208] The crosslinking agent can improve the heat resistance and chemical resistance of the formed film by causing a crosslinking reaction between the alkali-soluble polyimide resin or other added components. In this case, a compound containing a functional group such as an acryloyl group can be used as the crosslinking agent. In addition, as an example of a crosslinking agent, there is a thermal crosslinking agent, and a compound containing a thermally reactive functional group (such as a hydroxymethyl group, an epoxy group, etc.) can be used as such a thermal crosslinking agent.

[0209] Specific examples of the cross-linking agent may include: DML-PC, DML-PEP, DML-OC, DML-OEP, DML-34X, DML-PTBP, DML-PCHP, DML-OCHP, DML-PFP, DML-PSBP, DML-POP, DML-MBOC, DML-MBPC, DML-MTrisPC, DML-BisOC-Z, DML-BisOCHP-Z, DML-BPC, DML-BisOC-P, DMOM-PC, DMOM-PT BP, DMOM-MBPC, TriML-P, TriML-35XL, TML-HQ, TML-BP, TML-pp-BPF, TML-BPE, TML-BPA, TML-BPAF, TML-BPAP, TMOM-BP, TMOM-BPE, TMOM-BPA, TMOM-BPAF, TMOM-BPAP, HML-TPPHBA, HML-TPHAP, HMOM-TPPHBA, HMOM-TPHAP (trade names, all provided by Honshu Chemical Industry Co., Ltd.); "NIKALAC" (registered trademark) MX-290, "NIKALAC" (registered trademark) MX-280, "NIKALAC" (registered trademark) MX-270, "NIKALAC" (registered trademark) MX-279, "NIKALAC" (registered trademark) MW-100LM, "NIKALAC" (registered trademark) MX-750LM (trade names, all manufactured by Sanwa Chemical Co., Ltd.), etc., which are cross-linking agents commonly used in the art. According to one embodiment of the present disclosure, the content of the cross-linking agent is 10 to 30 parts by weight relative to 100 parts by weight of the photosensitive resin composition. However, the present disclosure is not limited to the above range.

[0210] In the case of a silane coupling agent, for example, it can be used to improve the dispersibility of thermally conductive fillers such as alumina, and as long as it can show the above effects, various types known in the art can be used without restriction. A silane coupling agent refers to a compound containing a hydrolyzable silyl group or a silanol group. In addition, a silane coupling agent can improve heat resistance and chemical resistance by improving the mutual adhesion between the film formed by curing and a specific surface of the substrate. Examples of silane coupling agents can include one or more selected from octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane, etc., but the present disclosure is not limited thereto. According to a preferred embodiment of the present disclosure, a mixture of two or more compounds selected from the aforementioned silane coupling agent group is preferably used.

[0211] The silane coupling agent may be included in an amount of 0.1 to 2 parts by weight relative to 100 parts by weight of the photosensitive resin composition. As a preferred example, the silane coupling agent may be included in an amount of 0.2 to 1 part by weight relative to 100 parts by weight of the photosensitive resin composition, but the present disclosure is not limited thereto.

[0212] According to one embodiment of the present disclosure, the aforementioned composition may further include a solvent.

[0213] According to one embodiment of the present disclosure, any compound known in the art to which the present disclosure pertains to forming a photosensitive resin composition may be used as a solvent without particular limitation. For example, the solvent may be one or more compounds selected from esters, ethers, ketones, aromatic hydrocarbons, and sulfoxides.

[0214] The ester-based solvent may be ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl lactate, ethyl lactate, γ-butyrolactone, ε-caprolactone, δ-valerolactone, alkyl oxyacetates (e.g., methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate (e.g., methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, etc.)), alkyl 3-oxypropionates (e.g., methyl 3-oxypropionate, ethyl 3-oxypropionate (e.g., methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, etc.) 2-Oxopropionic acid methyl ester, 2-Oxopropionic acid ethyl ester, 2-Oxopropionic acid propyl ester, etc. (e.g., 2-methoxypropionic acid methyl ester, 2-methoxypropionic acid ethyl ester, 2-methoxypropionic acid propyl ester, 2-ethoxypropionic acid methyl ester, 2-ethoxypropionic acid ethyl ester)), 2-Oxo-2-methylpropionic acid methyl ester and 2-Oxo-2-methylpropionic acid ethyl ester (e.g., 2-methoxy-2-methylpropionic acid methyl ester, 2-ethoxy-2-methylpropionic acid ethyl ester, etc.), methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, methyl 2-oxobutanoate, ethyl 2-oxobutanoate, etc.

[0215] The ether-based solvent can be diethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, and the like.

[0216] The ketone-based solvent may be methyl ethyl ketone, cyclohexanone, cyclopentanone, 2-heptanone, 3-heptanone, N-methyl-2-pyrrolidone, or the like.

[0217] The aromatic hydrocarbon-based solvent may be toluene, xylene, anisole, limonene, or the like.

[0218] Furthermore, the sulfoxide-based solvent can be appropriately selected from substances known to those skilled in the art and used.

[0219] According to one embodiment of the present disclosure, propylene glycol monomethyl acetate is used as the solvent.

[0220] According to one embodiment of the present disclosure, diethylene glycol ethyl methyl ether is used as the solvent.

[0221] According to one embodiment of the present disclosure, a material obtained by mixing propylene glycol monomethyl acetate and diethylene glycol ethyl methyl ether at a certain ratio is used as a solvent.

[0222] According to one embodiment of the present disclosure, the content of the solvent is 20 to 90 parts by weight relative to 100 parts by weight of the photosensitive resin composition. According to a preferred embodiment of the present disclosure, the content of the solvent is 20 to 80 parts by weight relative to 100 parts by weight of the photosensitive resin composition. According to a more preferred embodiment of the present disclosure, the content of the solvent is 40 to 80 parts by weight relative to 100 parts by weight of the photosensitive resin composition.

[0223] When the content of the solvent is within the above range, or when the mixing ratio is within the above range (if a mixed solution is used as a solvent), a coating film of the photosensitive resin composition having excellent applicability or flatness may be obtained.

[0224] According to one embodiment of the present disclosure, the photosensitive resin composition further comprises: a multifunctional monomer; a surfactant; a photopolymerization initiator; and a solvent, wherein relative to 100 parts by weight of the photosensitive resin composition, the content of the multifunctional monomer is 1 to 20 parts by weight, the content of the surfactant is 0.1 to 3 parts by weight, the content of the photopolymerization initiator is 1 to 10 parts by weight, and the content of the solvent is 40 to 80 parts by weight.

[0225] One embodiment of the present disclosure provides a photoresist including a photosensitive resin composition or a cured product thereof.

[0226] One embodiment of the present disclosure provides a photoresist prepared using the photosensitive resin composition or a cured product thereof.

[0227] More specifically, the photosensitive resin composition of the present disclosure is applied on a substrate by an appropriate method to form a thin film type or pattern type photoresist.

[0228] The photosensitive resin composition according to the present disclosure can be used for a thin film transistor-liquid crystal display (TFT-LCD) or an organic light emitting diode (OLED) display, a photoresist for forming a black matrix, a photoresist for forming an overcoat layer, a column spacer photoresist, a photocurable coating, a photocurable ink, a photocurable adhesive, a printing plate, a photoresist for a printed wiring board, a photoresist for a plasma display panel (PDP), and the like, and there is no particular limitation on its use.

[0229] The photoresist according to one embodiment of the present disclosure is used as an insulating film, a protective film, a planarizing film, or the like.

[0230] The photoresist according to one embodiment of the present disclosure is prepared by a low-temperature curing method of a photosensitive resin composition described later.

[0231] The photoresist according to one embodiment of the present disclosure has excellent chemical resistance. Specifically, when exposed to chemical agents, the change rate of thickness is small.

[0232] In the present disclosure, chemical resistance evaluation is performed by measuring a thickness change rate before and after the treatment when the photoresist is treated with one reagent at 50° C. to 70° C. for 200 to 300 seconds.

[0233] The thickness variation rate of the photoresist according to one embodiment of the present disclosure relative to a specific solvent is less than 5%. The thickness variation rate of the photoresist according to a preferred embodiment of the present disclosure relative to a specific solvent is less than 2%. The thickness variation rate of the photoresist according to a preferred embodiment of the present disclosure relative to a specific solvent is less than 1%. At this time, KOH, tetramethylammonium hydroxide (TMAH), oxalic acid aqueous solution, etc. can be used as specific solvents, but the present disclosure is not limited thereto. More specifically, 5% KOH, 2.38% tetramethylammonium hydroxide (TMAH), 5% oxalic acid aqueous solution, etc. can be used as specific solvents, but the present disclosure is not limited thereto.

[0234] The photoresist according to one embodiment of the present disclosure has a chemical resistance of 95% or greater. The photoresist according to one preferred embodiment of the present disclosure has a chemical resistance of 98% or greater. The photoresist according to one more preferred embodiment of the present disclosure has a chemical resistance of 99% or greater.

[0235] The photoresist according to one embodiment of the present disclosure has a minimum hole pattern characteristic of 7 μm or more. The photoresist according to one preferred embodiment of the present disclosure has a minimum hole pattern characteristic of 7 μm to 15 μm.

[0236] The photoresist according to one embodiment of the present disclosure has a chemical resistance of 95% or greater and a minimum hole pattern characteristic of 7 μm or greater. The photoresist according to one preferred embodiment of the present disclosure has a chemical resistance of 98% or greater and a minimum hole pattern characteristic of 7 μm to 15 μm. The photoresist according to one preferred embodiment of the present disclosure has a chemical resistance of 99% or greater and a minimum hole pattern characteristic of 8 μm to 14 μm.

[0237] The photoresist according to one embodiment of the present disclosure has a thickness variation rate of 5% or less with respect to 5% KOH, 2.38% tetramethylammonium hydroxide (TMAH), 5% oxalic acid, or a stripper (LGS-900 grade of LGC).

[0238] A display device is provided, which includes the above-mentioned photoresist according to the present disclosure.

[0239] The display device may be any one of the following: a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD), a touch screen panel (TSP), a thin film transistor-liquid crystal display (TFT-LCD), and a cathode ray tube (CRT).

[0240] Another embodiment of the present disclosure provides a low-temperature curing method for a photosensitive resin composition, comprising the following steps:

[0241] (a) coating the photosensitive resin composition on a substrate;

[0242] (b) drying or prebaking the coated substrate;

[0243] (c) exposing the dried or prebaked substrate to light;

[0244] (d) forming a pattern; and

[0245] (e) The substrate is post-baked at a temperature within a range of 50°C or higher and lower than 100°C.

[0246] In the present disclosure, step (a) (the step of applying the above-mentioned photosensitive resin composition on the substrate) means applying and coating the above-mentioned photosensitive resin composition on the substrate. The application and coating method is not particularly limited to existing coating methods, but spraying, roller coating, spin coating, etc. can be used, and generally, spin coating is widely used. However, it is not limited to the above examples and can be implemented by a method selected by a person of ordinary skill in the art. In addition, after the coating film is formed, the residual solvent can be partially removed under reduced pressure in some cases.

[0247] In the present disclosure, step (b) (the step of drying and / or pre-baking the coated substrate) means removing the solvent contained in the coating film.

[0248] According to one embodiment of the present disclosure, the step of drying and / or pre-baking the coated substrate may be a step of drying the coated substrate; pre-baking the coated substrate; or a step of drying and pre-baking the coated substrate. In this case, the step of drying and / or pre-baking the coated substrate may be a step of pre-baking the coated substrate after pre-drying the coated substrate; or drying and pre-baking the coated substrate at the same time, but is not limited to the above order, and a person of ordinary skill in the art may adjust the order.

[0249] According to one embodiment of the present disclosure, the drying step is performed by vacuum exhaust drying at 50 Pa to 70 Pa. However, the present disclosure is not limited to the above method.

[0250] The pre-baking step is preferably performed at a temperature that is the same as or lower than the temperature of the subsequent curing process. For example, the pre-baking step can be performed at a temperature range of about 80°C or higher and lower than 100°C for 1 minute to 5 minutes. As a preferred example, the pre-baking step can be performed at a temperature range of about 80°C or higher and lower than 100°C for 100 seconds to 180 seconds. As a more preferred example, the pre-baking step can be performed at a temperature range of about 80°C or higher and lower than 100°C for 100 seconds to 120 seconds.

[0251] According to one embodiment of the present disclosure, in step (c) (the step of exposing the dried or prebaked substrate to light), a photomask on which a pattern to be processed is formed may be used to irradiate ultraviolet light or visible light with a wavelength of 200 nm to 500 nm, and the exposure dose during irradiation is preferably 10 mJ / cm 2 Up to 4,000mJ / cm 2 The exposure time is not particularly limited and can be appropriately changed depending on the exposure device used, the wavelength of the irradiated light, the exposure dose, etc. However, the preferred exposure time can be changed within the range of 5 seconds to 250 seconds.

[0252] In the present disclosure, step (d) (patterning step) means selectively exposing the coating film to light using a mask to form a pattern on the substrate, and then developing the coating film exposed to light. In the step of forming the photosensitive resin film, a generally known alkaline aqueous developer that can be used in the steps of manufacturing semiconductors or displays can be used without particular limitation.

[0253] Hereinafter, embodiments will be given and described in detail to specifically describe the present disclosure. However, the embodiments according to the present disclosure can be modified into various other forms, and the scope of the present disclosure should not be interpreted as being limited to the embodiments described below. The embodiments of the present disclosure are provided to more fully illustrate the present disclosure to those of ordinary skill in the art.

[0254] <Preparation Example>

[0255] Preparation Example 1. Preparation of Composition 1

[0256] Composition 1 was obtained using the following: relative to 100 parts by weight of the photosensitive resin composition, 10 parts by weight of a binder resin represented by the following Chemical Formula 301, 0.1 parts by weight of a compound represented by the following Chemical Formula 101, 9 parts by weight of a multifunctional monomer, 0.3 parts by weight of a surfactant, 2 parts by weight of a photopolymerization initiator, and 78.6 parts by weight of a solvent.

[0257] [Chemical Formula 301]

[0258]

[0259] In Chemical Formula 301, a to d are mole fractions, and are a = 0.3, b = 0.2, c = 0.4, and d = 0.1, respectively. The weight average molecular weight of the binder resin represented by Chemical Formula 301 above is 10,000 g / mol. In order to polymerize the binder resin represented by Chemical Formula 301 above, the following monomers were used: styrene (Duksan Chemicals), methacrylic acid (MAA, Samchun Chemical Co., Ltd.), glycidyl methacrylate (GMA, Daejung Chemicals & Metals Co., Ltd.), and 3,4-epoxy-cyclohexylmethyl methacrylate (Cyclomer M100, Daicel Corporation). In the case of weight average molecular weight (Mw), the eluent was measured using tetrahydrofuran (tetrahydrofuran (stabilized) from JTBaker) by gel permeation chromatography (GPC) system (Viscotek, Malvern). As described above, the GPC measurement results of the binder resin represented by Chemical Formula 301 are shown in Figure 1 middle.

[0260] [Chemical Formula 101]

[0261]

[0262] In the above Preparation Example 1, a compound in which the number corresponding to x in CAS 9046-40-0 is an integer of 35 was used as the above Chemical Formula 101, dipentaerythritol hexaacrylate (DPHA) was used as a multifunctional monomer, 0.2 parts by weight of BYK-Chemie's BYK-331 and 0.1 parts by weight of DIC's TF-1140 were used as surfactants, Troonly's PBG-305 was used as a photopolymerization initiator, and 60 parts by weight of propylene glycol monomethyl ether acetate and 18.6 parts by weight of diethylene glycol ethyl methyl ether were used as solvents.

[0263] Preparation Examples 2 to 5. Preparation of Compositions 2 to 5

[0264] Compositions 2 to 5 were prepared in the same manner as in Preparation Example 1, except that in the preparation of the above composition 1, the compound represented by Chemical Formula 101 was used in amounts of 3 parts by weight, 5 parts by weight, 7 parts by weight, and 9 parts by weight, respectively. However, in each Preparation Example, the other components were reduced in the same proportion as the increased content of the compound represented by Chemical Formula 101 relative to 100 parts by weight of each composition.

[0265] Comparative Preparation 1 and Additional Preparations 1 and 2. Preparation of Comparative Composition 1 and Additional Compositions 1 and 2

[0266] Comparative composition 1 and additional compositions 1 and 2 were prepared in the same manner as in Preparation Example 1, except that in the above Preparation Example 1, the compound represented by Chemical Formula 101 was used in amounts of 0 parts by weight, 10 parts by weight, and 12 parts by weight, respectively. However, in each of the comparative preparation examples and the additional preparation examples, the other components were increased or decreased in the same proportion as the amount of the compound represented by Chemical Formula 101 was changed relative to 100 parts by weight of each composition.

[0267] Examples 1 to 5, Comparative Example 1, and Additional Experimental Examples 1 and 2

[0268] <Formation of Coating Film>

[0269] In Examples 1 to 5, Comparative Example 1, and Additional Experimental Examples 1 and 2, each composition prepared in Preparation Examples 1 to 5, Comparative Preparation Example 1, and Additional Preparation Examples 1 and 2 was applied to a substrate (SiNx, Ti / Al / Ti), spin-coated, and vacuum-dried at 65 Pa. The vacuum-dried composition was pre-baked on a hot plate at 85° C. for 110 seconds. The composition was exposed to light with a light source (i, g, h composite wavelength, projection type exposure machine) at 50 mJ / cm 2After the pre-baked material was exposed to light with an intensity of 100 nm, the light-exposed material was developed in 2.38% tetramethylammonium hydroxide (TMAH) at 23°C for 90 seconds. The developed material was washed with distilled water for 20 seconds and post-baked in a convection oven at 85°C for 60 minutes. A coating film having a hole pattern was formed. A mask in which a hole pattern with a size of 5 μm to 50 μm was divided was used as an exposure mask. In order to compare the difference in effect, post-baking was also performed at 100°C for 60 minutes.

[0270] <Evaluation of Coating Film>

[0271] [Evaluation of chemical resistance]

[0272] Each of the formed coating films was treated with a stripper (LGS-900 grade of LGC) at 65° C. for 200 seconds, and thickness values before and after the treatment were measured to determine the thickness change rate by the following residual film rate formula.

[0273] Residual film rate = (film thickness after treatment) / (film thickness before treatment)

[0274] [Evaluation of minimum hole pattern characteristics]

[0275] The minimum hole resolution was measured by applying a hole pattern mask. The hole pattern characteristics were analyzed by SNU 3D profilometer, optical microscope and SEM.

[0276] The results of the chemical resistance evaluation and the minimum hole pattern characteristic evaluation are shown in Table 1 below.

[0277] [Table 1]

[0278]

[0279] In the case of Examples 1 to 5 using Compositions 1 to 5 according to an embodiment of the present disclosure, it can be confirmed that both chemical resistance and minimum hole pattern characteristics are excellent. In particular, it can be confirmed that by including 0.1 to 9 parts by weight of the compound represented by Chemical Formula 1 according to one embodiment of the present disclosure, even after post-baking at a low temperature of 85°C, which is lower than 100°C, excellent chemical resistance of 99% or more is obtained. As a specific example, Figure 2 and Figure 3 The mask hole and minimum hole pattern characteristics of the micropore according to Example 1 are shown respectively, and it can be determined that when the mask hole is 8 μm (as shown in FIG. Figure 4 As shown), the minimum hole pattern is 7μm (as shown Figure 5 shown).

[0280] In the case of Comparative Example 1 using Comparative Composition 1, it can be confirmed that since the compound of Chemical Formula 1 according to the present disclosure is not included, the thickness of the coating film changes by 5% or more, at most 15%, and thus the chemical resistance is poor. Specifically, Figure 4 and Figure 5 The mask hole and minimum hole pattern characteristics of the micropore according to Comparative Example 1 are shown respectively, and it can be determined that when the mask hole is 8 μm (as shown in FIG. Figure 4 As shown), no minimum hole pattern is formed (as shown Figure 5 shown).

[0281] In the case of Additional Experimental Examples 1 and 2 using Additional Compositions 1 and 2, it was confirmed that the minimum hole pattern characteristics were poor because a pattern was not formed by including 10 parts by weight or more of the compound according to Chemical Formula 1 of the present disclosure relative to 100 parts by weight of the photosensitive resin composition. Specifically, when the compound according to Chemical Formula 1 of the present disclosure was included in an excessive amount, the curing reaction excessively proceeded before pattern formation proceeded, making it possible to determine that a pattern was not formed and the minimum hole pattern characteristics were poor.

[0282] As in the above results, it can be confirmed that the photosensitive resin composition according to the present disclosure or the cured product thereof is excellent in both its chemical resistance and pattern characteristics.

Claims

1. A photosensitive resin composition comprising a binder resin and a compound represented by the following Chemical Formula 1, [Chemical Formula 1] In Chemical Formula 1, A1 is -OH; -SH; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted amino group, "-" means the site of connection with Chemical Formula 1, A2 and A3 are the same as or different from each other and are each independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group, x is an integer from 20 to 50, The compound represented by the above Chemical Formula 1 is present in an amount of 0.05 to 9 parts by weight relative to 100 parts by weight of the photosensitive resin composition, and The binder resin includes a polymer containing repeating units of the following Chemical Formulas 3-1 to 3-4: [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3] [Chemical formula 3-4] In Chemical Formulas 3-1 to 3-4, Ar is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, L101 and L102 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group, R101 and R102 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group, T is a substituted or unsubstituted aliphatic hydrocarbon ring, a as a mole fraction is 0.3 to 0.4, b as a mole fraction is 0.1 to 0.2, c as a mole fraction is 0.2 to 0.4, d as a mole fraction is 0.1 to 0.3, and a+b+c+d=1, r101 is an integer of 1 to 3, and when r101 is 2 or greater, R101 are the same as or different from each other, r102 is an integer of 1 or greater, and when r102 is 2 or greater, R102 are the same as or different from each other, and It refers to the site of attachment of another moiety.

2. The photosensitive resin composition according to claim 1, wherein Ar is a substituted or unsubstituted C6 to C 20 Aryl; or substituted or unsubstituted C2 to C 20 Heterocyclic group.

3. The photosensitive resin composition according to claim 1, wherein L101 and L102 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted methylene group; a substituted or unsubstituted ethylene group; a substituted or unsubstituted propylene group; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

4. The photosensitive resin composition according to claim 1, wherein R101 and R102 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted C1 to C 10 Alkyl; substituted or unsubstituted C2 to C 10 Alkenyl; substituted or unsubstituted C6 to C 30 Aryl; or substituted or unsubstituted C2 to C 30 Heterocyclic group.

5. The photosensitive resin composition according to claim 1, wherein T is a substituted or unsubstituted C3 to C 10 Aliphatic hydrocarbon ring.

6. The photosensitive resin composition according to claim 1, wherein A2 and A3 are the same as or different from each other and are each independently substituted or unsubstituted C1 to C 10 alkyl.

7. The photosensitive resin composition according to claim 1, wherein the above Chemical Formula 1 is represented by the following Chemical Formula 11: [Chemical Formula 11] In Chemical Formula 11, A1 and x are as defined in Chemical Formula 1 above. 8 . The photosensitive resin composition according to claim 1 , further comprising at least one of: a multifunctional monomer; a surfactant; and a photopolymerization initiator. 9 . The photosensitive resin composition according to claim 1 , further comprising a solvent.

10. The photosensitive resin composition according to claim 1, further comprising: a multifunctional monomer; a surfactant; a photopolymerization initiator; and a solvent, wherein relative to 100 parts by weight of the photosensitive resin composition, the content of the multifunctional monomer is 1 to 20 parts by weight, the content of the surfactant is 0.1 to 3 parts by weight, the content of the photopolymerization initiator is 1 to 10 parts by weight, and the content of the solvent is 40 to 80 parts by weight. 11 . A photoresist comprising the photosensitive resin composition according to claim 1 or a cured product thereof. 12 . A display device comprising the photoresist according to claim 11 .

13. A low-temperature curing method for a photosensitive resin composition, comprising the following steps: (a) coating a photosensitive resin composition according to any one of claims 1 to 10 on a substrate; (b) drying or prebaking the coated substrate; (c) exposing the dried or prebaked substrate to light; (d) forming a pattern; as well as (e) post-baking the substrate at a temperature in a range of 50°C or higher and lower than 100°C.

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