Photosensitive resin composition and method for forming pattern using same

Abstract

The present disclosure relates to a photosensitive resin composition, a photoresist film and a substrate-protective film that are manufactured using same, and a method for forming a pattern using same. The photosensitive resin composition according to an embodiment has excellent chemical resistance and adhesion to a substrate, and, at the same time, can achieve high resolution when forming a pattern. In addition, a film formed using the photosensitive resin composition according to an embodiment has excellent physical properties and enables the formation of ultra-fine patterns, and thus is useful for application to display devices such as flat panel displays.

Description

Photosensitive resin composition and method for forming a pattern using the same

[0001] The present disclosure relates to a photosensitive resin composition and a method for forming a pattern using the same.

[0002] Flat panel displays are widely used in smartphones, tablet PCs, and televisions, and are classified into liquid crystal displays (LCDs), organic light-emitting displays (OLEDs), plasma display panels (PDPs), and electrophoretic displays depending on their light-emitting method. In the manufacturing process of these flat panel displays, a photo process is applied to form patterns, and a photosensitive resin composition is used at this time.

[0003] Photosensitive resins are representative functional polymer materials used in the production of various precision electronic and information industry products. These polymer compounds undergo chemical changes in their molecular structure upon light irradiation, resulting in changes in physical properties such as solubility in specific solvents, coloration, and curing. Photosensitive resins enable micro-precision processing, significantly reduce energy and raw material consumption compared to thermal reaction processes, and offer the advantages of rapid and accurate work in a small installation space.

[0004] Photosensitive resin compositions containing such photosensitive resins are classified into positive and negative types depending on the solubility of the exposed portion in the developing solution. Positive photoresists are those in which the exposed portion dissolves in the developing solution, while negative photoresists are those in which the exposed portion does not dissolve in the developing solution and the unexposed portion dissolves to form a pattern. Positive and negative photoresists differ in the binder resin, cross-linking agent, etc. used.

[0005] Meanwhile, with the recent advancements in electronic devices, such as high integration and micropatterning, there is a growing demand for photosensitive resins that can minimize defect rates and enhance processing efficiency and resolution. To address this issue, a method using a photosensitive resin containing polyimide has been introduced. Polyimide is a polymer with a hetero-imidine ring in its main chain, manufactured by condensation polymerization of tetracarboxylic acid and diamine. Polyimide exhibits excellent light transmittance, mechanical properties, thermal characteristics, and excellent substrate adhesion.

[0006] However, polyamide is easily hydrolyzed by water in the air, etc., so it has insufficient preservation and stability, and it has low adhesion to the substrate to which it is applied, and there is a problem that the physical properties of electrical wiring or substrates are deteriorated due to high temperature application. In addition, other types of photosensitive resins also have insufficient chemical resistance, heat resistance, and electrical properties in the final cured state, and especially, there is a problem that the adhesion to metal substrates is insufficient, so there is a problem of peeling from the substrate during the development or curing process.

[0007] Furthermore, the photosensitive composition must not only exhibit photosensitivity, but also be capable of low-temperature curing, exhibit reliability even with a short curing time, and exhibit enhanced light transmittance for superior lithographic performance. Furthermore, a positive-type photosensitive composition should preferably minimize the generation of developing waste products, as the exposed portion is soluble in an alkaline solution. Therefore, a new photosensitive resin composition that overcomes the shortcomings of conventional photosensitive resins and exhibits improved performance is needed.

[0008] One embodiment is to provide a photosensitive resin composition that has excellent adhesion to a substrate and chemical resistance, and at the same time can achieve high resolution when forming a pattern.

[0009] Another embodiment is to provide a photoresist film and a substrate protective film manufactured using the photosensitive resin composition.

[0010] Another embodiment provides a method for forming a pattern using the photosensitive resin composition.

[0011] One embodiment provides a photosensitive resin composition comprising (A) an acrylic-siloxane copolymer; (B) a photosensitizer; and (C) a solvent, wherein (A) the acrylic-siloxane copolymer comprises a repeating unit derived from a compound represented by the following chemical formula 1.

[0012] [Chemical Formula 1]

[0013]

[0014] In the above chemical formula 1,

[0015] R 1 is hydrogen, substituted or unsubstituted C 1-20 Alkyl group, substituted or unsubstituted C 3-20 Cycloalkyl group, substituted or unsubstituted C 6-20 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-20 is a heteroaryl group, and the above R 1 C substituted by 1-20 Alkyl group, C 3-20 Cycloalkyl group, C 6-20 Aryl group, and C 5-20 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-10 Alkyl group, and C 5-10 It may be substituted with at least one selected from the group consisting of cycloalkyl groups; and X is -Si(R) at the terminal 11 ) x1 (OR 12 ) x2 is a substituent linked to a group, and the above R 11 and R 12 are each independently hydrogen, substituted or unsubstituted C 1-20 Alkyl group, substituted or unsubstituted C 2-20 Alkenyl group, substituted or unsubstituted C 3-20Cycloalkyl group, or substituted or unsubstituted C 6-20 is an aryl group, and the above R 11 and R 12 C substituted by 1-20 Alkyl group, C 2-20 Alkenyl group, C 3-20 Cycloalkyl group, and C 6-20 Aryl groups are each independently -NO2, -NH2, C 1-10 Alkyl group, and C 5-10 It may be substituted with at least one selected from the group consisting of cycloalkyl groups, x1 is an integer from 0 to 2, x2 is an integer from 1 to 3, and x1+x2=3 is satisfied.

[0016] In one embodiment, in the above chemical formula 1, the R 1 is hydrogen, substituted or unsubstituted C 1-10 Alkyl group, substituted or unsubstituted C 5-10 Cycloalkyl group, substituted or unsubstituted C 6-10 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-10 is a heteroaryl group, and the above R 1 C substituted by 1-10 Alkyl group, C 5-10 Cycloalkyl group, C 6-10 Aryl group, and C 5-10 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-5 Alkyl group, and C 5-8 It may be substituted with at least one selected from the group consisting of cycloalkyl groups.

[0017] In one embodiment, the (A) acrylic-siloxane copolymer may include a repeating unit prepared by hydrolysis and condensation of at least one alkoxysilane compound represented by the following chemical formulae 2-1 to 2-3.

[0018] [Chemical Formula 2-1]

[0019] Si(R 21 )2(OR 22 )2

[0020] [Chemical Formula 2-2]

[0021] Si(R 23 )(OR 24 )3

[0022] [Chemical Formula 2-3]

[0023] Si(OR 25 )4

[0024] In the above chemical formulas 2-1 to 2-3, R 21 , R 22 , R 23 , R 24 , and R 25 are each independently hydrogen, substituted or unsubstituted C 1-20 Alkyl group, substituted or unsubstituted C 2-20 Alkenyl group, substituted or unsubstituted C 3-20 Cycloalkyl group, substituted or unsubstituted C 6-20 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-20 is a heteroaryl group, and the above R 21 , R 22 , R 23 , R 24 , and R 25 C substituted by 1-20 Alkyl group, C 2-20 Alkenyl group, C 3-20 Cycloalkyl group, C 6-20 Aryl group, and C 5-20 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-10 Alkyl group, and C 5-10 It may be substituted with at least one selected from the group consisting of cycloalkyl groups.

[0025] In one embodiment, in the chemical formulas 2-1 to 2-3, R 21 , R 22 , R 23, R 24 , and R 25 are each independently hydrogen, substituted or unsubstituted C 1-10 Alkyl group, substituted or unsubstituted C 2-10 Alkenyl group, or substituted or unsubstituted C 6-10 is an aryl group, and the above R 21 , R 22 , R 23 , R 24 , and R 25 C substituted by 1-10 Alkyl group, C 2-10 Alkenyl group and C 6-10 Aryl groups are each independently halogen, -NO2, -NH2, C 1-5 Alkyl group, and C 5-8 It may be substituted with at least one selected from the group consisting of cycloalkyl groups.

[0026] In one embodiment, the (A) acrylic-siloxane copolymer is selected from the group consisting of phenylethoxydimethoxysilane, phenylmethoxydiethoxysilane, methylethoxydimethoxysilane, methylmethoxydiethoxysilane, phenylphenoxydimethoxysilane, phenylphenoxydiethoxysilane, phenylmethoxydimephenoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, phenyltripropoxysilane, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, tetrabutoxysilane, methylphenyldimethoxysilane, dimethyldimethoxysilane, diphenyldimethoxysilane, methylethyldiethoxysilane, vinyltrimethoxysilane, and It may include a repeating unit manufactured by hydrolysis and condensation reaction of at least one compound selected from the group of compounds consisting of vinyltriethoxysilane.

[0027] In one embodiment, the (A) acrylic-siloxane copolymer may further comprise a repeating unit derived from a compound represented by the following chemical formula 3.

[0028] [Chemical Formula 3]

[0029]

[0030] In the above chemical formula 3, R 3 is hydrogen, substituted or unsubstituted C 1-20 Alkyl group, substituted or unsubstituted C 3-20 Cycloalkyl group, substituted or unsubstituted C 6-20 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-20 A heteroaryl group, and the substituted C 1-20 Alkyl group, C 3-20 Cycloalkyl group, C 6-20 Aryl group, and C 5-20 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-10 Alkyl group, and C 5-10 It may be substituted with at least one selected from the group consisting of cycloalkyl groups; Y is -OH, -COOH, an epoxy group, or C 1-5 is an alkyl group; and n can be an integer from 0 to 10.

[0031] In one embodiment, in the above chemical formula 3, the R 3 is hydrogen, substituted or unsubstituted C 1-10 Alkyl group, substituted or unsubstituted C 5-10 Cycloalkyl group, substituted or unsubstituted C 6-10 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-10 is a heteroaryl group, and the above R 3 C substituted by 1-10 Alkyl group, C 5-10 Cycloalkyl group, C 6-10 Aryl group, and C 5-10 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-5 Alkyl group, and C 5-8 It may be substituted with at least one selected from the group consisting of cycloalkyl groups.

[0032] In one embodiment, the repeating unit derived from the compound represented by the above chemical formula 3 is , , , , , , and It may be at least one selected from the group consisting of .

[0033] In one embodiment, the (A) acrylic-siloxane copolymer may further comprise a repeating unit derived from a compound represented by the following chemical formula 4.

[0034] [Chemical Formula 4]

[0035]

[0036] In the above chemical formula 4, R 4 is hydrogen, substituted or unsubstituted C 1-20 Alkyl group, substituted or unsubstituted C 3-20 Cycloalkyl group, substituted or unsubstituted C 6-20 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-20 A heteroaryl group, and the substituted C 1-20 Alkyl group, C 3-20 Cycloalkyl group, C 6-20 Aryl group, and C 5-20 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-10 Alkyl group, and C 5-10 It may be substituted with at least one selected from the group consisting of cycloalkyl groups; and m is an integer from 0 to 10.

[0037] In one embodiment, in the above chemical formula 4, the R 4 is hydrogen, substituted or unsubstituted C 1-10 Alkyl group, substituted or unsubstituted C 5-10 Cycloalkyl group, substituted or unsubstituted C 6-10An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-10 is a heteroaryl group, and the above R 4 C substituted by 1-10 Alkyl group, C 5-10 Cycloalkyl group, C 6-10 Aryl group, and C 5-10 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-5 Alkyl group, and C 5-8 It may be substituted with at least one selected from the group consisting of cycloalkyl groups.

[0038] In one embodiment, the photosensitive resin composition may further comprise (D) a siloxane polymer.

[0039] In one embodiment, the (D) siloxane polymer may include a repeating unit prepared by hydrolysis and condensation reaction of at least one alkoxysilane compound represented by the following chemical formulae 5-1 to 5-3.

[0040] [Chemical Formula 5-1]

[0041] Si(R 51 )2(OR 52 )2

[0042] [Chemical Formula 5-2]

[0043] Si(R 53 )(OR 54 )3

[0044] [Chemical Formula 5-3]

[0045] Si(OR 55 )4

[0046] In the above chemical formulas 5-1 to 5-3, R 51 , R 52 , R 53 , R 54 , and R 55 are each independently hydrogen, substituted or unsubstituted C 1-20Alkyl group, substituted or unsubstituted C 2-20 Alkenyl group, substituted or unsubstituted C 3-20 Cycloalkyl group, substituted or unsubstituted C 6-20 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-20 is a heteroaryl group, and the above R 51 , R 52 , R 53 , R 54 , and R 55 C substituted by 1-20 Alkyl group, C 2-20 Alkenyl group, C 3-20 Cycloalkyl group, C 6-20 Aryl group, and C 5-20 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-10 Alkyl group, and C 5-10 It may be substituted with at least one selected from the group consisting of cycloalkyl groups.

[0047] In one embodiment, the R 51 , R 52 , R 53 , R 54 , and R 55 are each independently hydrogen, substituted or unsubstituted C 1-10 Alkyl group, substituted or unsubstituted C 2-10 Alkenyl group, or substituted or unsubstituted C 6-10 is an aryl group, and the above R 51 , R 52 , R 53 , R 54 , and R 55 C substituted by 1-10 Alkyl group, C 2-10 Alkenyl group and C 6-10 Aryl groups are each independently halogen, -NO2, -NH2, C 1-5 Alkyl group, and C 5-8 It may be substituted with at least one selected from the group consisting of cycloalkyl groups.

[0048] In one embodiment, the (D) siloxane polymer is selected from the group consisting of phenylethoxydimethoxysilane, phenylmethoxydiethoxysilane, methylethoxydimethoxysilane, methylmethoxydiethoxysilane, phenylphenoxydimethoxysilane, phenylphenoxydiethoxysilane, phenylmethoxydimephenoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, phenyltripropoxysilane, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, tetrabutoxysilane, methylphenyldimethoxysilane, dimethyldimethoxysilane, diphenyldimethoxysilane, methylethyldiethoxysilane, vinyltrimethoxysilane, and It may include a repeating unit manufactured by hydrolysis and condensation reaction of at least one compound selected from the group of compounds consisting of vinyltriethoxysilane.

[0049] In one embodiment, in the above formula 1, X is -L 1 -Si(R 11 ) x1 (OR 12 ) x2 and the above L 1 Silver substituted or unsubstituted C 1-10 A combination of one or more substituents selected from the group consisting of alkylene groups, -COO-, and -O-, and the L 1 C substituted by 1-10 The alkylene group may be substituted with one or more selected from the group consisting of halogen, -NO2, -NH2, and -OH.

[0050] In one embodiment, the molecular weight of the (A) acrylic-siloxane copolymer may be from 1,000 g / mol to 100,000 g / mol.

[0051] In one embodiment, the molecular weight of the (D) siloxane polymer may be from 1,000 g / mol to 50,000 g / mol.

[0052] Another embodiment provides a photoresist film and a substrate protective film manufactured using the photosensitive resin composition according to the above embodiment.

[0053] Another embodiment provides a method for forming a pattern, comprising: a step of applying a photosensitive resin composition according to the above embodiment onto a substrate to produce a photoresist film; a step of exposing the photoresist film; and a step of developing the exposed photoresist film using a developer.

[0054] The present disclosure relates to a photosensitive resin composition, a photoresist film and a substrate protective film manufactured using the same, and a method for forming a pattern using the same. According to one embodiment, the photosensitive resin composition exhibits excellent adhesion to a substrate and chemical resistance, and simultaneously enables high resolution during pattern formation. Furthermore, a film formed using the photosensitive resin composition according to one embodiment exhibits excellent physical properties while also enabling the implementation of an ultra-fine pattern, making it useful for application to display devices such as flat panel displays.

[0055] The embodiments described in this specification may be modified in many different forms, and thus the technology according to one implementation is not limited to the embodiments described below. Furthermore, throughout the specification, the terms "comprising," "including," "containing," "includes," or "having" a component do not exclude other components unless specifically stated to the contrary, but rather mean that other components may be included, and do not exclude additional elements, materials, or processes that are not listed.

[0056] The numerical ranges used herein include the lower and upper limits and all values ​​within that range, increments logically derived from the shape and width of the defined range, all doubly defined values, and all possible combinations of the upper and lower limits of numerical ranges defined in different shapes. For example, if the content of a composition is defined as 10% to 80% or 20% to 50%, the numerical ranges of 10% to 50% or 50% to 80% should also be interpreted as being described herein. Unless otherwise specified herein, values ​​outside the numerical range that may arise due to experimental error or rounding of values ​​are also included in the defined numerical range.

[0057] Unless otherwise specifically defined herein, a drug may be considered to be a value within 30%, 25%, 20%, 15%, 10%, 5%, 3%, 2%, 1% or 0.5% of the stated value.

[0058] The term “alkylene group” as used herein means a straight or branched chain diradical of carbon saturated bonds, which may be substituted with any substituent.

[0059] The term "alkyl group" as used herein refers to a straight or branched chain radical of carbon-carbon saturated bonds, which may be substituted with any substituent. The term "alkenyl group" as used herein refers to a straight or branched carbon chain radical containing one or more carbon-carbon unsaturated bonds (double bonds), which may be substituted with any substituent. In this case, the unsaturated bond may be located at the end of the carbon chain or in the middle.

[0060] The term "aryl" as used herein is not limited to a bridged ring, a spiro ring, or a fused ring. For example, the aryl may be benzene, naphthalene, fluorene, anthracene, phenanthrene, bibenzene, triphenylene, pyrene, or chrysene.

[0061] The term "halogen" as used herein may be any one or more selected from the group consisting of I, Br, Cl and F.

[0062] Hereinafter, the present disclosure will be described in detail (with reference to the attached drawings). However, this is merely exemplary and the present disclosure is not limited to the specific embodiments described as examples.

[0063] One embodiment provides a photosensitive resin composition comprising (A) an acrylic-siloxane copolymer; (B) a photosensitizer; and (C) a solvent, wherein the (A) acrylic-siloxane copolymer comprises a repeating unit derived from a compound represented by the following chemical formula 1.

[0064] [Chemical Formula 1]

[0065]

[0066] In the above chemical formula 1,

[0067] R 1 is hydrogen, substituted or unsubstituted C 1-20 Alkyl group, substituted or unsubstituted C 3-20 Cycloalkyl group, substituted or unsubstituted C 6-20 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-20 It is a heteroaryl group,

[0068] The above R 1 C substituted by 1-20 Alkyl group, C 3-20 Cycloalkyl group, C 6-20 Aryl group, and C 5-20 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-10 Alkyl group, and C 5-10 It may be substituted with at least one selected from the group consisting of cycloalkyl groups; and

[0069] X is at the end -Si(R11 ) x1 (OR 12 ) x2 is a substituent that is connected to a base,

[0070] The above R 11 and R 12 are each independently hydrogen, substituted or unsubstituted C 1-20 Alkyl group, substituted or unsubstituted C 2-20 Alkenyl group, substituted or unsubstituted C 3-20 Cycloalkyl group, or substituted or unsubstituted C 6-20 It is an aryl group,

[0071] The above R 11 and R 12 C substituted by 1-20 Alkyl group, C 2-20 Alkenyl group, C 3-20 Cycloalkyl group, and C 6-20 Aryl groups are each independently -NO2, -NH2, C 1-10 Alkyl group, and C 5-10 It may be substituted with at least one selected from the group consisting of cycloalkyl groups,

[0072] x1 is an integer from 0 to 2, x2 is an integer from 1 to 3, and satisfies x1+x2=3.

[0073] In one embodiment, the photosensitive resin composition may individually contain the components comprising (A) to (C), or may be in a form in which the components comprising (A) to (C) are mixed and at least partially reacted.

[0074] In one embodiment, R of the above formula 1 1 is hydrogen, substituted or unsubstituted C 1-15 Alkyl group, substituted or unsubstituted C 1-10 Alkyl group, substituted or unsubstituted C 1-8 Alkyl group, substituted or unsubstituted C 1-5 Alkyl group, substituted or unsubstituted C 1-3 Alkyl group, ethyl group, methyl group, substituted or unsubstituted C 3-15Cycloalkyl group, substituted or unsubstituted C 5-10 Cycloalkyl group, substituted or unsubstituted C 5-8 Cycloalkyl group, substituted or unsubstituted C 5-6 Cycloalkyl group, substituted or unsubstituted C 6-15 Aryl group, substituted or unsubstituted C 6-10 An aryl group, a substituted or unsubstituted C6 aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O, and S. 5-15 Heteroaryl group, substituted or unsubstituted C 5-10 Heteroaryl group, substituted or unsubstituted C 5-8 Heteroaryl group, or substituted or unsubstituted C 5-6 It may be a heteroaryl group.

[0075] In one embodiment, R of the above chemical formula 1 1 Silver halogen, -NO2, -NH2, C 1-8 Alkyl group, C 1-6 Alkyl group, C 1-5 Alkyl group, C 1-3 Alkyl group, ethyl group, methyl group, C 5-10 Cycloalkyl group, C 5-8 Cycloalkyl group, and C 5-6 It may be substituted with one or more selected from the group consisting of cycloalkyl groups.

[0076] Specifically, the R of the above chemical formula 1 1 is hydrogen, substituted or unsubstituted C 1-10 Alkyl group, substituted or unsubstituted C 5-10 Cycloalkyl group, substituted or unsubstituted C 6-10 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-10 is a heteroaryl group, and the above R 1 C substituted by 1-10 Alkyl group, C 5-10 Cycloalkyl group, C 6-10 Aryl group, and C 5-10Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-5 Alkyl group, and C 5-8 It may be substituted with at least one selected from the group consisting of cycloalkyl groups.

[0077] In one embodiment, the R 11 and R 12 are each independently hydrogen, substituted or unsubstituted C 1-15 Alkyl group, substituted or unsubstituted C 1-10 Alkyl group, substituted or unsubstituted C 1-8 Alkyl group, substituted or unsubstituted C 1-5 Alkyl group, substituted or unsubstituted C 1-3 Alkyl group, ethyl group, methyl group, substituted or unsubstituted C 2-15 Alkenyl group, substituted or unsubstituted C 2-10 Alkenyl group, substituted or unsubstituted C 2-8 Alkenyl group, substituted or unsubstituted C 2-5 Alkenyl group, substituted or unsubstituted C 2-3 Alkenyl group, vinyl group, substituted or unsubstituted C 3-15 Cycloalkyl group, substituted or unsubstituted C 5-10 Cycloalkyl group, substituted or unsubstituted C 5-8 Cycloalkyl group, substituted or unsubstituted C 5-6 Cycloalkyl group, substituted or unsubstituted C 6-15 Aryl group, substituted or unsubstituted C 6-10 It may be an aryl group, or a substituted or unsubstituted C6 aryl group.

[0078] In one embodiment, the R 11 and R 12 is halogen, -NO2, -NH2, C 1-8 Alkyl group, C 1-6 Alkyl group, C 1-5 Alkyl group, C 1-3 Alkyl group, ethyl group, methyl group, C 5-10 Cycloalkyl group, C 5-8 Cycloalkyl group, and C 5-6It may be substituted with one or more selected from the group consisting of cycloalkyl groups.

[0079] In one embodiment, x1 may be 0 and x2 may be 3; x1 may be 1 and x2 may be 2; or x1 may be 2 and x2 may be 3.

[0080] In one embodiment, the (A) acrylic-siloxane copolymer may include a repeating unit prepared by hydrolysis and condensation reaction of at least one alkoxysilane compound represented by the following chemical formulae 2-1 to 2-3.

[0081] [Chemical Formula 2-1]

[0082] Si(R 21 )2(OR 22 )2

[0083] [Chemical Formula 2-2]

[0084] Si(R 23 )(OR 24 )3

[0085] [Chemical Formula 2-3]

[0086] Si(OR 25 )4

[0087] In the above chemical formulas 2-1 to 2-3,

[0088] R 21 , R 22 , R 23 , R 24 , and R 25 are each independently hydrogen, substituted or unsubstituted C 1-20 Alkyl group, substituted or unsubstituted C 2-20 Alkenyl group, substituted or unsubstituted C 3-20 Cycloalkyl group, substituted or unsubstituted C 6-20 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-20 It is a heteroaryl group,

[0089] The above R 21, R 22 , R 23 , R 24 , and R 25 C substituted by 1-20 Alkyl group, C 2-20 Alkenyl group, C 3-20 Cycloalkyl group, C 6-20 Aryl group, and C 5-20 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-10 Alkyl group, and C 5-10 It may be substituted with at least one selected from the group consisting of cycloalkyl groups.

[0090] In one embodiment, R 21 , R 22 , R 23 , R 24 , and R 25 are each independently hydrogen, substituted or unsubstituted C 1-15 Alkyl group, substituted or unsubstituted C 1-10 Alkyl group, substituted or unsubstituted C 1-8 Alkyl group, substituted or unsubstituted C 1-5 Alkyl group, substituted or unsubstituted C 1-3 Alkyl group, ethyl group, methyl group, substituted or unsubstituted C 2-15 Alkenyl group, substituted or unsubstituted C 2-10 Alkenyl group, substituted or unsubstituted C 2-8 Alkenyl group, substituted or unsubstituted C 2-5 Alkenyl group, vinyl group, substituted or unsubstituted C 3-15 Cycloalkyl group, substituted or unsubstituted C 5-10 Cycloalkyl group, substituted or unsubstituted C 5-8 Cycloalkyl group, substituted or unsubstituted C 5-6 Cycloalkyl group, substituted or unsubstituted C 6-15 Aryl group, substituted or unsubstituted C 6-10 An aryl group, a substituted or unsubstituted C6 aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O, and S. 5-15Heteroaryl group, substituted or unsubstituted C 5-10 Heteroaryl group, substituted or unsubstituted C 5-8 Heteroaryl group, or substituted or unsubstituted C 5-6 It may be a heteroaryl group.

[0091] In one embodiment, the R 21 , R 22 , R 23 , R 24 , and R 25 are each independently halogen, -NO2, -NH2, C 1-8 Alkyl group, C 1-6 Alkyl group, C 1-5 Alkyl group, C 1-3 Alkyl group, ethyl group, methyl group, C 5-10 Cycloalkyl group, C 5-8 Cycloalkyl group, and C 5-6 It may be substituted with one or more selected from the group consisting of cycloalkyl groups.

[0092] In one embodiment, in the chemical formulas 2-1 to 2-3, R 21 , R 22 , R 23 , R 24 , and R 25 are each independently hydrogen, substituted or unsubstituted C 1-10 Alkyl group, substituted or unsubstituted C 2-10 Alkenyl group, or substituted or unsubstituted C 6-10 is an aryl group, and the above R 21 , R 22 , R 23 , R 24 , and R 25 C substituted by 1-10 Alkyl group, C 2-10 Alkenyl group and C 6-10 Aryl groups are each independently halogen, -NO2, -NH2, C 1-5 Alkyl group, and C 5-8 It may be substituted with at least one selected from the group consisting of cycloalkyl groups.

[0093] In one embodiment, the (A) acrylic-siloxane copolymer is selected from the group consisting of phenylethoxydimethoxysilane, phenylmethoxydiethoxysilane, methylethoxydimethoxysilane, methylmethoxydiethoxysilane, phenylphenoxydimethoxysilane, phenylphenoxydiethoxysilane, phenylmethoxydimephenoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, phenyltripropoxysilane, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, tetrabutoxysilane, methylphenyldimethoxysilane, dimethyldimethoxysilane, diphenyldimethoxysilane, methylethyldiethoxysilane, vinyltrimethoxysilane, and It may include a repeating unit manufactured by hydrolysis and condensation reaction of at least one compound selected from a group of compounds consisting of vinyltriethoxysilane.

[0094] In one embodiment, the (A) acrylic-siloxane copolymer may further comprise a repeating unit derived from a compound represented by the following chemical formula 3.

[0095] [Chemical Formula 3]

[0096]

[0097] In the above chemical formula 3,

[0098] R 3 is hydrogen, substituted or unsubstituted C 1-20 Alkyl group, substituted or unsubstituted C 3-20 Cycloalkyl group, substituted or unsubstituted C 6-20 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-20 It is a heteroaryl group,

[0099] The above substituted C 1-20 Alkyl group, C 3-20 Cycloalkyl group, C 6-20 Aryl group, and C 5-20 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-10 Alkyl group, and C 5-10It may be substituted with at least one selected from the group consisting of cycloalkyl groups;

[0100] Y is -OH, -COOH, epoxy group, or C 1-5 is an alkyl group; and

[0101] n is an integer from 0 to 10.

[0102] In one embodiment, R of the above chemical formula 3 3 is hydrogen, substituted or unsubstituted C 1-15 Alkyl group, substituted or unsubstituted C 1-10 Alkyl group, substituted or unsubstituted C 1-8 Alkyl group, substituted or unsubstituted C 1-5 Alkyl group, substituted or unsubstituted C 1-3 Alkyl group, ethyl group, methyl group, substituted or unsubstituted C 2-15 Alkenyl group, substituted or unsubstituted C 2-10 Alkenyl group, substituted or unsubstituted C 2-8 Alkenyl group, substituted or unsubstituted C 2-5 Alkenyl group, substituted or unsubstituted C 2-3 Alkenyl group, vinyl group, substituted or unsubstituted C 3-15 Cycloalkyl group, substituted or unsubstituted C 5-10 Cycloalkyl group, substituted or unsubstituted C 5-8 Cycloalkyl group, substituted or unsubstituted C 5-6 Cycloalkyl group, substituted or unsubstituted C 6-15 Aryl group, substituted or unsubstituted C 6-10 An aryl group, a substituted or unsubstituted C6 aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O, and S. 5-15 Heteroaryl group, substituted or unsubstituted C 5-10 Heteroaryl group, substituted or unsubstituted C 5-8 Heteroaryl group, or substituted or unsubstituted C 5-6 It may be a heteroaryl group.

[0103] In one embodiment, R of the above chemical formula 3 3 Silver halogen, -NO2, -NH2, C 1-8 Alkyl group, C 1-6 Alkyl group, C 1-5 Alkyl group, C 1-3 Alkyl group, ethyl group, methyl group, C 5-10 Cycloalkyl group, C 5-8 Cycloalkyl group, and C 5-6 It may be substituted with one or more selected from the group consisting of cycloalkyl groups.

[0104] In one embodiment, in the above chemical formula 3, the R 3 is hydrogen, substituted or unsubstituted C 1-10 Alkyl group, substituted or unsubstituted C 5-10 Cycloalkyl group, substituted or unsubstituted C 6-10 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-10 is a heteroaryl group, and the above R 3 C substituted by 1-10 Alkyl group, C 5-10 Cycloalkyl group, C 6-10 Aryl group, and C 5-10 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-5 Alkyl group, and C 5-8 It may be substituted with at least one selected from the group consisting of cycloalkyl groups.

[0105] In one embodiment, Y of the above chemical formula 3 is -OH, -COOH, epoxy group (-C2H3O), C 1-3 It can be an alkyl group, an ethyl group, or a methyl group.

[0106] In one embodiment, n may be an integer from 0 to 8, from 0 to 5, from 1 to 5, from 1 to 3, 0, 1, 2, or 3.

[0107] In one embodiment, the repeating unit derived from the compound represented by the above chemical formula 3 may be at least one selected from the following group: , , , , , , and

[0108] In one embodiment, the (A) acrylic-siloxane copolymer may further comprise a repeating unit derived from a compound represented by the following chemical formula 4.

[0109] [Chemical Formula 4]

[0110]

[0111] In the above chemical formula 4, R 4 is hydrogen, substituted or unsubstituted C 1-20 Alkyl group, substituted or unsubstituted C 3-20 Cycloalkyl group, substituted or unsubstituted C 6-20 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-20 It is a heteroaryl group,

[0112] The above substituted C 1-20 Alkyl group, C 3-20 Cycloalkyl group, C 6-20 Aryl group, and C 5-20 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-10 Alkyl group, and C 5-10 It may be substituted with at least one selected from the group consisting of cycloalkyl groups; and

[0113] m is an integer from 0 to 10.

[0114] In one embodiment, R of the above chemical formula 4 4 is hydrogen, substituted or unsubstituted C 1-15 Alkyl group, substituted or unsubstituted C 1-10 Alkyl group, substituted or unsubstituted C1-8 Alkyl group, substituted or unsubstituted C 1-5 Alkyl group, substituted or unsubstituted C 1-3 Alkyl group, ethyl group, methyl group, substituted or unsubstituted C 3-15 Cycloalkyl group, substituted or unsubstituted C 5-10 Cycloalkyl group, substituted or unsubstituted C 5-8 Cycloalkyl group, substituted or unsubstituted C 5-6 Cycloalkyl group, substituted or unsubstituted C 6-15 Aryl group, substituted or unsubstituted C 6-10 An aryl group, a substituted or unsubstituted C6 aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O, and S. 5-15 Heteroaryl group, substituted or unsubstituted C 5-10 Heteroaryl group, substituted or unsubstituted C 5-8 Heteroaryl group, or substituted or unsubstituted C 5-6 It may be a heteroaryl group.

[0115] In one embodiment, R of the above chemical formula 4 4 Silver halogen, -NO2, -NH2, C 1-8 Alkyl group, C 1-6 Alkyl group, C 1-5 Alkyl group, C 1-3 Alkyl group, ethyl group, methyl group, C 5-10 Cycloalkyl group, C 5-8 Cycloalkyl group, and C 5-6 It may be substituted with one or more selected from the group consisting of cycloalkyl groups.

[0116] In one embodiment, m can be an integer from 0 to 8, from 0 to 5, from 0 to 3, from 1 to 3, 0, 1, 2, or 3.

[0117] In one embodiment, in the above chemical formula 4, the R 4 is hydrogen, substituted or unsubstituted C 1-10 Alkyl group, substituted or unsubstituted C 5-10Cycloalkyl group, substituted or unsubstituted C 6-10 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-10 is a heteroaryl group, and the above R 4 C substituted by 1-10 Alkyl group, C 5-10 Cycloalkyl group, C 6-10 Aryl group, and C 5-10 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-5 Alkyl group, and C 5-8 It may be substituted with at least one selected from the group consisting of cycloalkyl groups.

[0118] According to one embodiment, a photosensitive resin composition can be excellently implemented in hardness, resolution, sensitivity, crack resistance, and chemical resistance by including (A) an acrylic-siloxane copolymer (as a binder).

[0119] In one embodiment, the photosensitive resin composition may further comprise (D) a siloxane polymer.

[0120] In one embodiment, the photosensitive resin composition may individually contain the components comprising (A) to (D), or may be in a form in which the components comprising (A) to (D) are mixed and at least partially reacted.

[0121] In one embodiment, the (D) siloxane polymer may include a repeating unit prepared by hydrolysis and condensation of one or more alkoxysilane compounds represented by the following chemical formulae 5-1 to 5-3.

[0122] [Chemical Formula 5-1]

[0123] Si(R 51 )2(OR 52 )2

[0124] [Chemical Formula 5-2]

[0125] Si(R 53 )(OR 54 )3

[0126] [Chemical Formula 5-3]

[0127] Si(OR 55 )4

[0128] In the above chemical formulas 5-1 to 5-3,

[0129] R 51 , R 52 , R 53 , R 54 , and R 55 are each independently hydrogen, substituted or unsubstituted C 1-20 Alkyl group, substituted or unsubstituted C 2-20 Alkenyl group, substituted or unsubstituted C 3-20 Cycloalkyl group, substituted or unsubstituted C 6-20 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-20 It is a heteroaryl group,

[0130] The above R 51 , R 52 , R 53 , R 54 , and R 55 C substituted by 1-20 Alkyl group, C 2-20 Alkenyl group, C 3-20 Cycloalkyl group, C 6-20 Aryl group, and C 5-20 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-10 Alkyl group, and C 5-10 It may be substituted with at least one selected from the group consisting of cycloalkyl groups.

[0131] In one embodiment, R 51 , R 52 , R 53 , R 54 , and R 55 are each independently hydrogen, substituted or unsubstituted C 1-15Alkyl group, substituted or unsubstituted C 1-10 Alkyl group, substituted or unsubstituted C 1-8 Alkyl group, substituted or unsubstituted C 1-5 Alkyl group, substituted or unsubstituted C 1-3 Alkyl group, ethyl group, methyl group, substituted or unsubstituted C 2-15 Alkenyl group, substituted or unsubstituted C 2-10 Alkenyl group, substituted or unsubstituted C 2-8 Alkenyl group, substituted or unsubstituted C 2-5 Alkenyl group, vinyl group, substituted or unsubstituted C 3-15 Cycloalkyl group, substituted or unsubstituted C 5-10 Cycloalkyl group, substituted or unsubstituted C 5-8 Cycloalkyl group, substituted or unsubstituted C 5-6 Cycloalkyl group, substituted or unsubstituted C 6-15 Aryl group, substituted or unsubstituted C 6-10 An aryl group, a substituted or unsubstituted C6 aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O, and S. 5-15 Heteroaryl group, substituted or unsubstituted C 5-10 Heteroaryl group, substituted or unsubstituted C 5-8 Heteroaryl group, or substituted or unsubstituted C 5-6 It may be a heteroaryl group.

[0132] In one embodiment, the R 51 , R 52 , R 53 , R 54 , and R 55 are each independently halogen, -NO2, -NH2, C 1-8 Alkyl group, C 1-6 Alkyl group, C 1-5 Alkyl group, C 1-3 Alkyl group, ethyl group, methyl group, C 5-10 Cycloalkyl group, C 5-8 Cycloalkyl group, and C 5-6It may be substituted with one or more selected from the group consisting of cycloalkyl groups.

[0133] In one embodiment, in the chemical formulas 5-1 to 5-3, the R 51 , R 52 , R 53 , R 54 , and R 55 are each independently hydrogen, substituted or unsubstituted C 1-10 Alkyl group, substituted or unsubstituted C 2-10 Alkenyl group, or substituted or unsubstituted C 6-10 is an aryl group, and the above R 51 , R 52 , R 53 , R 54 , and R 55 C substituted by 1-10 Alkyl group, C 2-10 Alkenyl group and C 6-10 Aryl groups are each independently halogen, -NO2, -NH2, C 1-5 Alkyl group, and C 5-8 It may be substituted with at least one selected from the group consisting of cycloalkyl groups.

[0134] In one embodiment, the (D) siloxane polymer is selected from the group consisting of phenylethoxydimethoxysilane, phenylmethoxydiethoxysilane, methylethoxydimethoxysilane, methylmethoxydiethoxysilane, phenylphenoxydimethoxysilane, phenylphenoxydiethoxysilane, phenylmethoxydimephenoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, phenyltripropoxysilane, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, tetrabutoxysilane, methylphenyldimethoxysilane, dimethyldimethoxysilane, diphenyldimethoxysilane, methylethyldiethoxysilane, vinyltrimethoxysilane, and It may include a repeating unit manufactured by hydrolysis and condensation reaction of at least one compound selected from a group of compounds consisting of vinyltriethoxysilane.

[0135] In one embodiment, the siloxane used in the polymer of the (A) acrylic-siloxane copolymer and the (D) siloxane polymer may be the same or different.

[0136] In one embodiment, in the above formula 1, X is -L 1 -Si(OR 11 )3 and the above L 1 Silver substituted or unsubstituted C 1-10 A combination of one or more substituents selected from the group consisting of alkylene groups, -COO-, and -O-; wherein L 1 C substituted by 1-10 The alkylene group may be substituted with one or more selected from the group consisting of halogen, -NO2, -NH2, and -OH.

[0137] In one embodiment, L in the above formula 1 1 Silver substituted or unsubstituted C 1-8 Alkylene group, substituted or unsubstituted C 1-6 Alkylene group, substituted or unsubstituted C 1-5 Alkylene group, substituted or unsubstituted C 2-5 Alkylene group, substituted or unsubstituted C 2-3 It can be an alkylene group, an ethylene group, or a propylene group.

[0138] In one embodiment, the L 1 It may be substituted with one or more selected from the group consisting of halogen, -NO2, -NH2, and -OH.

[0139] In one embodiment, the molecular weight of the (A) acrylic-siloxane copolymer is not particularly limited, but may be 1,000 g / mol to 100,000 g / mol, 1,000 g / mol to 80,000 g / mol, 1,000 g / mol to 50,000 g / mol, 5,000 g / mol to 50,000 g / mol, 10,000 g / mol to 50,000 g / mol, 10,000 g / mol to 30,000 g / mol, or 10,000 g / mol to 20,000 g / mol.

[0140] In one embodiment, the (A) acrylic-siloxane copolymer may be a copolymer of an acrylic polymer and a siloxane polymer, and the weight ratio or molar ratio of the acrylic polymer and the siloxane polymer during polymerization is not particularly limited.

[0141] In one embodiment, the molecular weight of the (D) siloxane polymer is not particularly limited, but may be 1,000 g / mol to 50,000 g / mol, 1,000 g / mol to 30,000 g / mol, 3,000 g / mol to 30,000 g / mol, 3,000 g / mol to 10,000 g / mol, or 5,000 g / mol to 10,000 g / mol.

[0142] In one embodiment, when the photosensitive resin composition includes both (A) an acrylic-siloxane copolymer and (D) a siloxane polymer, the weight ratio of the (A) acrylic-siloxane copolymer and the (D) siloxane polymer is not particularly limited, but may be, for example, 1:1 to 1:10, 1:1 to 1:5, 1:1 to 1:3, 1:1 to 1:2, 1:1.2 to 1:2, or 1:1.5 to 1:2.

[0143] In one embodiment, the (B) photosensitizer may be, for example, a 1,2-quinonediazide compound (DNQ), and the 1,2-quinonediazide compound may be, for example, a compound used as a photosensitizer in the field of resists. Specific examples include an ester of a phenol compound and 1,2-benzoquinonediazide-4-sulfonic acid or 1,2-benzoquinonediazide-5-sulfonic acid; an ester of a phenol compound and 1,2-naphthoquinonediazide-4-sulfonic acid or 1,2-naphthoquinonediazide-5-sulfonic acid; a sulfonamide of a compound in which a hydroxyl group of a phenol compound is substituted with an amino group and 1,2-benzoquinonediazide-4-sulfonic acid or 1,2-benzoquinonediazide-5-sulfonic acid; Or, compounds in which the hydroxyl group of a phenol compound is substituted with an amino group, and sulfonamides such as 1,2-naphthoquinonediazide-4-sulfonic acid or 1,2-naphthoquinonediazide-5-sulfonic acid may be mentioned. The above substances may be used alone or in combination of two or more.

[0144] The above phenol compounds are 2,3,4-trihydroxybenzophenone, 2,4,6-trihydroxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone, 2,3,3',4-tetrahydroxybenzophenone, 2,3,4,4'-tetrahydroxybenzophenone, bis(2,4-dihydroxyphenyl)methane, bis(p-hydroxyphenyl)methane, tri(p-hydroxyphenyl)methane, 1,1,1-tri(p-hydroxyphenyl)ethane, bis(2,3,4-trihydroxyphenyl)methane, 2,2-bis(2,3,4-trihydroxyphenyl)propane, 1,1,3-tris(2,5-dimethyl-4-hydroxyphenyl)-3-phenylpropane, 4,4'-[1-[4-[1-[4-hydroxyphenyl]-1-methylethyl]phenyl]ethylidene]bisphenol, bis(2,5-dimethyl-4-hydroxyphenyl)-2-hydroxyphenylmethane, 3,3,3',3'-tetramethyl-1,1'-spirobiindene-5,6,7,5',6',7'-hexanol, and 2,2,4-trimethyl-7,2',4'-trihydroxyflavan.

[0145] The above 1,2-quinonediazide compound may be an ester of 2,3,4-trihydroxybenzophenone and 1,2-naphthoquinonediazide-4-sulfonic acid, an ester of 2,3,4-trihydroxybenzophenone and 1,2-naphthoquinonediazide-5-sulfonic acid, an ester of 4,4'-[1-[4-[1-[4-hydroxyphenyl]-1-methylethyl]phenyl]ethylidene]bisphenol and 1,2-naphthoquinonediazide-4-sulfonic acid, or an ester of 4,4'-[1-[4-[1-[4-hydroxyphenyl]-1-methylethyl]phenyl]ethylidene]bisphenol and 1,2-naphthoquinonediazide-5-sulfonic acid. These can be used alone or in combination of two or more, and these materials can improve the transparency of the positive photosensitive resin composition.

[0146] In one embodiment, the solvent (D) may be an organic solvent selected from solvents capable of uniformly dissolving or dispersing each component of the photosensitive resin composition. Specific examples thereof include ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether; diethylene glycol dialkyl ethers such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, and diethylene glycol dibutyl ether; ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate; propylene glycol monoalkyl ethers such as propylene glycol monomethyl ether (PGME) and propylene glycol monoethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate (propylene glycol-1-monomethyl ether-2-acetate), propylene glycol monoethyl ether acetate (PGMEA), and propylene glycol monopropyl ether acetate; aromatic hydrocarbons such as benzene, toluene, and xylene; ketones such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, and cyclohexanone; and alcohols such as isopropanol and propanediol. These solvents can be used alone or in combination of two or more, and the content varies depending on the coating method and the required thickness of the coating film.

[0147] In one embodiment, the photosensitive resin composition may further include a surfactant, an adhesive aid, a photoinitiator, etc.

[0148] The above surfactants include, for example, BM-1000, BM-1100 (manufactured by BM CHEMIE), Megapack F142 D, Megapack F172, Megapack F173, Megapack F183, F-470, F-471, F-475, F-482, F-489 (manufactured by Dainippon Ink & Kagaku Kogyo Co., Ltd.), Florard FC-135, Florard FC-170C, Florard FC-430, Florard FC-431 (manufactured by Sumitomo 3M Co., Ltd.), Surflon S-112, Surflon S-113, Surflon S-131, Surflon S-141, Surflon S-145, Surflon S-382, Surflon SC-101, Surflon SC-102, Surflon SC-103, Surflon SC-104, Surflon SC-105, Surflon SC-106 (manufactured by Asahi Glass Co., Ltd.), F-Top EF301, F-Top 303, F-Top 352 (manufactured by Shin-Akita Kasei Co., Ltd.), SH-28 PA, SH-190, SH-193, SZ-6032, SF-8428, DC-57, DC-190 (manufactured by Toray Silicone Co., Ltd.), DC3PA, DC7PA, SH11PA, SH21PA, SH8400, GE, FZ-2100, FZ-2110, FZ-2122, FZ-2222, FZ-2233 (manufactured by Dow Corning Toray Silicone Co., Ltd.), TSF-4440, TSF-4300, TSF-4445, TSF-4446, Examples thereof include fluorine-based and silicone-based surfactants such as TSF-4460, TSF-4452 (manufactured by Toshiba Silicone Co., Ltd.), and BYK-333 (manufactured by BYK Co., Ltd.); nonionic surfactants such as polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, and polyoxyethylene oleyl ether; polyoxyethylene aryl ethers such as polyoxyethylene octylphenyl ether, and polyoxyethylene nonylphenyl ether; and polyoxyethylene dialkyl esters such as polyoxyethylene dilaurate and polyoxyethylene distearate; and organosiloxane polymer KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), (meth)acrylic acid copolymer Polyflow No. 57, 95 (manufactured by Kyoeisha Oil and Fat Chemical Co., Ltd.).These can be used alone or in combination of two or more. The surfactant is preferably used in an amount of 0.05 to 10 parts by weight, and more preferably 0.1 to 5 parts by weight, per 100 parts by weight (based on solid content) of the polysiloxane compound. When the content of the surfactant is 0.05 parts by weight or more, the applicability is improved and cracks do not occur on the applied surface, and when it is 10 parts by weight or less, it is advantageous in terms of price.

[0149] In one embodiment, the acrylic-siloxane copolymer can be prepared by hydrolysis and condensation of monomers, which can be carried out in the presence of an acidic catalyst or a basic catalyst. Water and an acidic or basic catalyst can be used for hydrolysis. Examples of acid catalysts include formic acid, acetic acid, trifluoroacetic acid, nitric acid, sulfuric acid, hydrochloric acid, hydrofluoric acid, boric acid, and a cation exchange resin. Examples of basic catalysts include ammonia, triethylamine, monoethanolamine, diethanolamine, triethanolamine, sodium hydroxide, sodium nitrate, sodium bicarbonate, potassium hydroxide, and anion exchange resin. The polymerization temperature is not particularly limited, but may typically range from 10°C to 150°C. The polymerization time is also not particularly limited, but may typically be carried out for 1 hour to 48 hours. In addition, the polymerization reaction can be carried out under any pressure, including increased pressure, reduced pressure, or atmospheric pressure. After polymerization, low molecular weight components may be removed by distillation to stabilize the polysiloxane compound.

[0150] In one embodiment, the photosensitive resin composition may further include a thermal polymerization initiator, and the thermal polymerization initiator may be, for example, a peroxide-based compound. Specifically, for example, the thermal polymerization initiator may be a peroxydicarbonate-based compound, a peroxyester-based compound, or a peroxycyclohexane-based compound, but is not particularly limited as long as it is a peroxide-based initiator compound that reacts with a carbon-carbon unsaturated bond contained in polysiloxane. Specifically, for example, the thermal polymerization initiator may be 1,1-bis(t-butylperoxy)-3,3,5-trimethyl cyclohexane, 1,1-bis(t-hexylperoxy)-3,3,5-trimethylcyclohexane, 1,1-di(t-amylperoxy)cyclohexane, 1,1-bis(thexylperoxy)cyclohexane, 1,1-bis(t-butylperoxy)cyclohexane, It may be 2,2-di(t-butylperoxy)butane, or butyl 4,4-di(tbutylperoxy)valerate.

[0151] The photosensitive resin composition according to one embodiment may be a positive photosensitive resin composition.

[0152] The photosensitive resin composition according to one embodiment may further include one or more additives to improve resolution, coating uniformity, developability, or adhesiveness. Examples of such additives include a dispersant including an acrylic, styrene, polyethyleneimine, or urethane polymer; anionic, cationic, nonionic, or fluorine-based surfactants; coating improvers such as silicone resins; adhesion improvers (adhesion aids) such as silane coupling agents; ultraviolet absorbers such as alkoxybenzophenones; coagulation inhibitors such as sodium polyacrylate; thermal crosslinking agents such as epoxy compounds, melamine compounds, or bisazide compounds; and alkaline solubility accelerators such as organic carboxylic acids.

[0153] Specific examples of the above silane coupling agent include trimethoxysilylbenzoic acid, γ-methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, γ-isocyanatopropyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, N-phenyl-3-aminopropyltriethoxysilane, etc., and these may be used alone or in combination of two or more. Preferably, in terms of film residue rate and adhesion to the substrate, γ-isocyanatopropyltriethoxysilane and / or N-phenyl-3-aminopropyltriethoxysilane may be used. The content of the silane coupling agent of the present invention is preferably 0.01 to 10 parts by weight, and more preferably 0.1 to 5 parts by weight, based on 100 parts by weight (based on solid content) of the polysiloxane compound. When the content of the silane coupling agent is 0.01 parts by weight or more, adhesion to a substrate is improved, and when it is 10 parts by weight or less, thermal stability at high temperatures is improved, and the phenomenon of staining occurring after development can be prevented.

[0154] The photosensitive resin composition according to one embodiment has properties such as high solvent resistance, high water resistance, high acid resistance, high alkali resistance, high heat resistance, high transparency, and high adhesion to a substrate, which are generally required for patterned transparent films and insulating films, for example.

[0155] According to one embodiment, the photosensitive resin composition has excellent solvent resistance, acid resistance, alkali resistance, heat resistance, and transparency, so that transparent films, insulating films, display elements, etc. using the positive type photosensitive resin composition do not cause surface roughness in the resin film even when immersion, contact, or heat treatment is performed using a solvent, acid, or alkaline solution in the post-manufacturing process. Therefore, since the transparent film, etc. using the positive type photosensitive resin composition according to the present invention has high light transmittance, the display element, etc. using the same can improve the display quality of the product.

[0156] Another embodiment provides a photosensitive resin manufactured using the photosensitive resin composition according to the above embodiment.

[0157] Another embodiment provides a photoresist film manufactured using the photosensitive resin composition according to the above embodiment.

[0158] Another embodiment provides a substrate protective film manufactured using the photosensitive resin composition according to the above embodiment.

[0159] Another embodiment provides a display device including a substrate protective film according to the above embodiment.

[0160] Another embodiment provides a method for forming a pattern, comprising: a step of applying a photosensitive resin composition according to the above embodiment onto a substrate to produce a photoresist film; a step of exposing the photoresist film; and a step of developing the exposed photoresist film using a developer.

[0161] Light sources used in the investigation include low-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps, and argon gas lasers. In some cases, X-rays and electron beams can also be used. The exposure dose varies depending on the type and mixing amount of each component of the composition and the dry film thickness, but when using a high-pressure mercury lamp, it is 500 mJ / cm. 2 (by 365 nm sensor) may be less than or equal to:

[0162] A photosensitive resin composition according to one embodiment has excellent surface hardness and excellent adhesion to a substrate, so that it can be easily used in the manufacture of a substrate protective film, and a substrate protective film manufactured therefrom has excellent physical properties.

[0163] In a method for manufacturing a substrate protective film using a photosensitive resin composition according to one embodiment, the temperature and time for curing may be any temperature and time within a range that can be recognized by a person skilled in the art.

[0164] Hereinafter, specific examples and experimental examples are provided to illustrate the present invention. However, the examples and experimental examples described below are merely illustrative of some embodiments of one implementation, and therefore, the technology described in this specification should not be construed as being limited thereto.

[0165] <Example 1> Preparation of acrylic polymer

[0166] A 2,000 mL three-necked flask was charged with 1,300 g of propylene glycol methyl ether acetate (PGMEA) and heated to 95°C. Then, 235 g of methyl methacrylate, 102 g of 2-hydroxymethyl methacrylate, 161 g of styrene, 95 g of 3-methacryloxypropyltrimethoxysilane, and 11.2 g of t-butylperoxyoctoate as a thermal initiator were mixed in a dropping funnel, and the mixture was quantitatively added to the three-necked flask while maintaining the temperature for 3 hours. After that, the temperature was maintained for 6 hours and the final reaction was completed. Upon completion of the final reaction, an acrylic polymer having a molecular weight of 15,000 g / mol and a solid concentration of 30 wt% was obtained.

[0167] <Example 2> Preparation of acrylic polymer

[0168] In a 2,000 mL three-necked flask, 1,150 g of propylene glycol methyl ether acetate (PGMEA) and 250 g of propylene glycol methyl ether (PGME) were added and the temperature was raised to 95°C. Then, 181 g of methyl methacrylate, 83 g of 2-hydroxymethyl methacrylate, 151 g of styrene, 78 g of methyl methacrylic acid, and 24.5 g of t-butyl peroxyoctoate as a thermal initiator were mixed in a dropping funnel, and the temperature was maintained for 3 hours before being quantitatively added to the three-necked flask. After maintaining the temperature for 6 hours, 10.4 g of 3-glycidyl propyl trimethoxy silane was added dropwise and stirred for an additional hour to complete the final reaction. The final reaction was completed, and an acrylic polymer having a molecular weight of 15,000 g / mol and a solid concentration of 30 wt% was obtained.

[0169] <Example 3> Preparation of siloxane polymer

[0170] In a 2,000 mL three-necked flask, 215 g of phenyltrimethoxysilane, 391 g of methyltriethoxysilane, 230 g of tetraethoxysilane, and 150 g of propylene glycol methyl ether acetate (PGMEA) were added, and 250 g of water and 1.2 g of phosphoric acid were mixed and added over 30 minutes while stirring at room temperature.

[0171] After the addition was completed, the temperature was increased by heating with a temperature-controllable mantle and the condensation reaction was carried out at a temperature of approximately 80°C for 60 minutes. Thereafter, the temperature of the solution was increased by heating for 60 minutes so that the temperature was between approximately 90°C and 100°C. At this time, 502 g of alcohol and water, which were by-products during the reaction, were discharged, and the condensation reaction was maintained at the increased temperature for 2 hours before the final reaction was completed. After the final reaction was completed, a siloxane polymer having a molecular weight of 7,000 g / mol was obtained by diluting it with PGMEA so that the solid concentration became 30 wt%.

[0172] <Example 4> Preparation of acrylic-siloxane copolymer

[0173] In a 2,000 mL three-necked flask, 215 g of phenyltrimethoxysilane, 391 g of methyltriethoxysilane, 230 g of tetraethoxysilane, and 150 g of propylene glycol methyl ether acetate (PGMEA) were added, and 250 g of water and 1.2 g of phosphoric acid were mixed and added over 30 minutes while stirring at room temperature.

[0174] After the addition was completed, 341 g of the acrylic polymer manufactured in Example 1 was added and maintained for 30 minutes, and then the temperature was increased by heating with a temperature-controllable mantle to conduct a condensation reaction at a temperature of about 80°C for 60 minutes. Thereafter, the temperature of the solution was increased by heating for 60 minutes so that the temperature was between about 90°C and 100°C. At this time, 502 g of alcohol and water, which were by-products during the reaction, were discharged, and the condensation reaction was maintained at the increased temperature for 2 hours and then the final reaction was terminated. After the final reaction was terminated, an acrylic-siloxane copolymer having a molecular weight of 25,000 g / mol, diluted with PGMEA so that the solid concentration became 30 wt%, was obtained.

[0175] <Example 5> Preparation of acrylic-siloxane copolymer

[0176] In a 2,000 mL three-necked flask, 295 g of phenyltrimethoxysilane, 141 g of methyltriethoxysilane, 168 g of tetraethoxysilane, and 136 g of PGMEA were added, and 214 g of water and 1.15 g of phosphoric acid were mixed and added over 30 minutes while stirring at room temperature.

[0177] After the addition was completed, 383 g of the acrylic polymer manufactured in Example 2 was added and maintained for 30 minutes, and then the temperature was increased by heating with a temperature-controllable mantle to conduct a condensation reaction at a temperature of about 80°C for 60 minutes. Thereafter, the temperature of the solution was increased by heating for 60 minutes so that the temperature was between about 90°C and 100°C. At this time, 461 g of alcohol and water, which were by-products during the reaction, were discharged, and the condensation reaction was maintained at the increased temperature for 2 hours and then the final reaction was terminated. After the final reaction was terminated, an acrylic-siloxane copolymer having a molecular weight of 6,000 g / mol, which was diluted with PGMEA so that the solid concentration became 30 wt%, was obtained.

[0178] <Example 6> Preparation of acrylic-siloxane copolymer

[0179] In a 2,000 mL three-necked flask, 379 g of phenyltrimethoxysilane, 241 g of vinyltrimethoxysilane, 368 g of tetraethoxysilane, and 136 g of PGMEA were added, and 212 g of water and 2.15 g of phosphoric acid were mixed and added over 30 minutes while stirring at room temperature.

[0180] After the addition was completed, 373 g of the acrylic polymer manufactured in Example 2 was added and maintained for 30 minutes, and then the temperature was increased by heating with a temperature-controllable mantle to conduct a condensation reaction at a temperature of about 80°C for 60 minutes. Thereafter, the temperature of the solution was increased by heating for 60 minutes so that the temperature was between about 90°C and 100°C. At this time, 378 g of alcohol and water, which were by-products during the reaction, were discharged, and the condensation reaction was maintained at the increased temperature for 2 hours and then the final reaction was terminated. After the final reaction was terminated, an acrylic-siloxane copolymer having a molecular weight of 35,000 g / mol, which was diluted with PGMEA so that the solid concentration became 30 wt%, was obtained.

[0181] <Example 7> Preparation of photosensitive resin composition

[0182] 11.24 g of the acrylic-siloxane copolymer prepared in Example 4, 1.5 g of a quinonediazide compound (TPPA-520) from Miwon, 0.042 g of a leveling surfactant (BYK 333 silicone surfactant) from BYK, 0.084 g of an adhesive aid (KBE-9007 from Shin-Etsu), and 0.5 g of a thermal polymerization initiator, 1,1-bis(t-butylperoxycyclohexane), were added to 8.2 g of propylene glycol-1-monomethyl ether-2-acetate and stirred to prepare a photosensitive resin composition.

[0183] <Example 8> Preparation of photosensitive resin composition

[0184] 12.11 g of the acrylic-siloxane copolymer prepared in Example 5, 1.5 g of a quinonediazide compound (TPPA-520) from Miwon, 0.042 g of a leveling surfactant (BYK 333 silicone surfactant) from BYK, 0.084 g of an adhesive aid (KBE-9007 from Shin-Etsu), and 0.5 g of 1,1-bis(t-butylperoxycyclohexane) as a thermal polymerization initiator were added to 8.2 g of propylene glycol-1-monomethyl ether-2-acetate and stirred to prepare a photosensitive resin composition.

[0185] <Example 9> Preparation of photosensitive resin composition

[0186] 10.97 g of the acrylic-siloxane copolymer prepared in Example 6, 1.5 g of a quinonediazide compound (TPPA-520) from Miwon, 0.042 g of a leveling surfactant (BYK 333 silicone surfactant) from BYK, 0.084 g of an adhesive aid (KBE-9007 from Shin-Etsu), and 0.5 g of a thermal polymerization initiator, 1,1-bis(t-butylperoxycyclohexane), were added to 8.2 g of propylene glycol-1-monomethyl ether-2-acetate and stirred to prepare a photosensitive resin composition.

[0187] <Example 10> Preparation of photosensitive resin composition

[0188] 9.3 g of the siloxane polymer prepared in Example 3, 5.24 g of the acrylic-siloxane copolymer prepared in Example 4, 1.5 g of a quinonediazide compound (TPPA-520) from Miwon, 0.042 g of a leveling surfactant (BYK 333 silicone surfactant) from BYK, 0.084 g of an adhesive aid (KBE-9007 from Shin-Etsu), and 0.5 g of 1,1-bis(t-butylperoxycyclohexane) as a thermal polymerization initiator were added to 8.2 g of propylene glycol-1-monomethyl ether-2-acetate and stirred to prepare a photosensitive resin composition.

[0189] <Example 11> Preparation of photosensitive resin composition

[0190] 8.3 g of the siloxane polymer prepared in Example 3, 4.66 g of the acrylic-siloxane copolymer prepared in Example 5, 1.5 g of a quinonediazide compound (TPPA-520) from Miwon, 0.042 g of a leveling surfactant (BYK 333 silicone surfactant) from BYK, 0.084 g of an adhesive aid (KBE-9007 from Shin-Etsu), and 0.5 g of 1,1-bis(t-butylperoxycyclohexane) as a thermal polymerization initiator were added to 8.2 g of propylene glycol-1-monomethyl ether-2-acetate and stirred to prepare a photosensitive resin composition.

[0191] <Example 12> Preparation of photosensitive resin composition

[0192] 9.13 g of the siloxane polymer prepared in Example 3, 6.73 g of the acrylic-siloxane copolymer prepared in Example 6, 1.5 g of a quinonediazide compound (TPPA-520) from Miwon, 0.042 g of a leveling surfactant (BYK 333 silicone surfactant) from BYK, 0.084 g of an adhesive aid (KBE-9007 from Shin-Etsu), and 0.5 g of 1,1-bis(t-butylperoxycyclohexane) as a thermal polymerization initiator were added to 8.2 g of propylene glycol-1-monomethyl ether-2-acetate and stirred to prepare a photosensitive resin composition.

[0193] <Comparative Example 1> Preparation of photosensitive resin composition

[0194] In a 2,000 mL three-necked flask, 1,150 g of propylene glycol methyl ether acetate (PGMEA) and 250 g of propylene glycol methyl ether (PGME) were added and the temperature was raised to 95°C. Then, 181 g of methyl methacrylate, 83 g of 2-hydroxymethyl methacrylate, 151 g of styrene, 78 g of methyl methacrylic acid, and 24.5 g of t-butyl peroxyoctoate as a thermal initiator were mixed in a dropping funnel, and the temperature was maintained for 3 hours before quantitatively adding them to the three-necked flask. After that, the temperature was maintained for 6 hours and the final reaction was completed. Upon completion of the final reaction, an acrylic polymer having a molecular weight of 15,000 g / mol and a solid content concentration of 30 wt% was obtained.

[0195] Next, 13.5 g of the above acrylic polymer, 1.5 g of Miwon Corporation's quinonediazide compound (TPPA-520), 0.042 g of BYK Corporation's leveling surfactant (BYK 333 silicone surfactant), and 0.084 g of adhesive aid (Shin-Etsu Corporation KBE-9007) were added to 8.2 g of propylene glycol-1-monomethyl ether-2-acetate and stirred to prepare a photosensitive resin composition.

[0196] <Comparative Example 2> Preparation of photosensitive resin composition

[0197] 190.3 g of vinyltriethoxysilane, 178.3 g of methyltriethoxysilane, 208.3 g of tetraethoxysilane, and 1 L of butyl acetate were placed in a three-necked flask with a volume of approximately 2 L, and a solution of 2 mL of 1 mol / L nitric acid and 180 mL of purified water was added dropwise over 30 minutes using a dropping funnel installed therein while vigorously stirring the contents of the flask. As a result, an exothermic reaction occurred in the contents of the flask, and initially it was a white, cloudy solution, but as the stirring continued, it became a colorless, transparent solution. After neutralizing the mixture, 1,000 mL of toluene and 1,000 mL of water were added, and the mixture was separated into two layers. The separated organic layer was concentrated under reduced pressure to remove the solvent. The molecular weight of the obtained siloxane polymer was measured and confirmed to have a weight average molecular weight of 2,500 g / mol.

[0198] Next, 10.2 g of the above siloxane polymer, 8.4 g of the acrylic polymer prepared in Comparative Example 1, 1.5 g of a quinonediazide compound (TPPA-520) from Miwon, 0.042 g of a leveling surfactant (BYK 333 silicone surfactant) from BYK, 0.084 g of an adhesive aid (KBE-9007 from Shin-Etsu), and 0.5 g of 1,1-bis(t-butylperoxycyclohexane) as a thermal polymerization initiator were added to 8.2 g of propylene glycol-1-monomethyl ether-2-acetate and stirred to prepare a photosensitive resin composition.

[0199] <Experimental Example>

[0200] 1. Forming a video pattern

[0201] The photosensitive resin compositions of Examples 6 to 11, Comparative Examples 1 and 2 were applied to a substrate that had undergone a predetermined pretreatment using a spin coating method to a thickness of 4 μm, and then heated at a temperature of 100° C. for 2 minutes to remove the solvent, thereby forming a coating film.

[0202] In order to form the required pattern on the obtained film, a mask of a predetermined shape was inserted, and then an active line of 365 nm was irradiated using a high-pressure mercury lamp (30 mJ / cm 2 ) Then, an alkaline aqueous solution was used as a developer to dissolve and remove unnecessary parts, leaving only the exposed portion to form a pattern. After the image pattern obtained by development was cooled to room temperature, it was post-baked at 230°C for 20 minutes in a hot air circulation dryer to obtain an image pattern.

[0203] 2. Surface hardness evaluation

[0204] The surface hardness of the cured film was measured using the method described in ASTM-D3363 using the substrate manufactured through the above 1. image pattern formation. Specifically, a Mitsubishi pencil was brought into contact with the substrate using a pencil hardness tester, and then a 500 g weight was placed on top of the pencil hardness tester to increase the load, while scratching the surface of the substrate at a speed of 50 mm / sec and observing the surface to measure the hardness. The measurement standard was evaluated based on when no signs of wear, peeling, tearing, or scratching of the surface were observed at a level corresponding to the pencil hardness.

[0205] 3. Resolution Evaluation

[0206] In order to measure the resolution of the image pattern of the substrate manufactured through the above 1. image pattern formation, the resolution was measured by observing the minimum size of the contact hole formed using a micro-optical microscope.

[0207] 4. Sensitivity Evaluation

[0208] In order to evaluate the sensitivity of the above composition, a mask having a circle type contact hole shape of 10 μm in size was used in the exposure process among the substrate methods manufactured through the formation of the image pattern in the above 1. The substrate on which the composition was formed was exposed to an exposure dose of 10 mJ to 50 mJ, and a development process was performed with an alkaline aqueous developer, and an image pattern was obtained by post-baking at 230°C for 20 minutes in a hot air circulation drying oven. The sensitivity was evaluated by confirming the exposure dose at which the image pattern was formed to be 10 μm in size, which is the same as the mask size.

[0209] 5. Crack resistance evaluation

[0210] In order to evaluate the crack resistance of the image pattern of the substrate manufactured through the above 1. image pattern formation, the substrate was immersed in a stripper (LGS-900) at 60 degrees for 5 minutes and then heat-treated three times at 230 degrees for 30 minutes to check whether cracks occurred.

[0211] 6. Chemical resistance evaluation

[0212] The substrate manufactured through the above 1. image pattern formation was immersed in etchant and stripper solutions under the following conditions to check the degree of damage to the coating film on the upper part of the substrate from the etchant and stripper solutions. The immersion conditions are as follows: immersed in BOE (buffered oxide etchant) etchant at room temperature for 3 hours, and the thickness and surface were checked using a non-contact thickness measuring device (ellipsometer) and the surface condition through an optical microscope, and then immersed in LGS-900 stripper at 60 ℃ for 10 minutes to check the thickness and surface. If surface damage was confirmed, it was evaluated as ○, and if no damage was confirmed, it was evaluated as ×. In addition, the thickness before and after BOE immersion and before and after LGS-900 immersion were calculated, and the change rate was calculated. At this time, the smaller the thickness deviation and the less surface damage, the better the chemical resistance.

[0213] The results of the above evaluation are shown in Table 1 below.

[0214] Hardness Resolution (μm) Sensitivity (mJ) Crack resistance Chemical resistance (thickness change / damage) BOELGS-900 Example 65H435×97% / ×99% / × Example 75H435×96% / ×100% / × Example 86H435×96% / ×101% / × Example 96H335×96% / ×99% / × Example 105H435×94% / ×99% / × Example 117H335×94% / ×100% / × Comparative Example 15H880×crack114% / ○ Comparative Example 25H430○crack121% / ○

[0215] As can be seen from Table 1 above, the substrates formed with patterns using the photosensitive resin compositions according to Examples 7 to 12, which are manufactured using an acrylic-siloxane copolymer, all exhibited properties that were at least equivalent to or superior to those of the comparative examples in the above-mentioned physical property evaluations. Specifically, Examples 7 to 12, in which an acrylic-siloxane copolymer binder resin was used, exhibited a clear superiority in the evaluations of resolution, sensitivity, and chemical resistance compared to Comparative Example 1, in which an acrylic polymer was used alone, and exhibited a clear superiority in the evaluations of crack resistance and chemical resistance compared to Comparative Example 2, in which a photosensitive resin composition was manufactured by simply mixing an acrylic polymer and a siloxane polymer.

[0216] Above, although an embodiment has been described in detail through examples and experimental examples, the scope of an embodiment is not limited to a specific example, and should be interpreted in accordance with the appended patent claims.

Claims

1. (A) Acrylic-siloxane copolymer; (B) photosensitizer; and (C) Contains a solvent, The above (A) acrylic-siloxane copolymer is a photosensitive resin composition comprising a repeating unit derived from a compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, R 1 is hydrogen, substituted or unsubstituted C 1-20 Alkyl group, substituted or unsubstituted C 3-20 Cycloalkyl group, substituted or unsubstituted C 6-20 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-20 It is a heteroaryl group, The above R 1 C substituted by 1-20 Alkyl group, C 3-20 Cycloalkyl group, C 6-20 Aryl group, and C 5-20 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-10 Alkyl group, and C 5-10 It may be substituted with at least one selected from the group consisting of cycloalkyl groups; and X is at the end -Si(R 11 ) x1 (OR 12 ) x2 is a substituent that is connected to a base, The above R 11 and R 12 are each independently hydrogen, substituted or unsubstituted C 1-20 Alkyl group, substituted or unsubstituted C 2-20 Alkenyl group, substituted or unsubstituted C 3-20 Cycloalkyl group, or substituted or unsubstituted C 6-20 It is an aryl group, The above R 11 and R 12 C substituted by 1-20 Alkyl group, C 2-20 Alkenyl group, C 3-20 Cycloalkyl group, and C 6-20 Aryl groups are each independently -NO2, -NH2, C 1-10 Alkyl group, and C 5-10 It may be substituted with at least one selected from the group consisting of cycloalkyl groups, x1 is an integer from 0 to 2, x2 is an integer from 1 to 3, and satisfies x1+x2=3.

2. In paragraph 1, In the above chemical formula 1, The above R 1 is hydrogen, substituted or unsubstituted C 1-10 Alkyl group, substituted or unsubstituted C 5-10 Cycloalkyl group, substituted or unsubstituted C 6-10 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-10 It is a heteroaryl group, The above R 1 C substituted by 1-10 Alkyl group, C 5-10 Cycloalkyl group, C 6-10 Aryl group, and C 5-10 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-5 Alkyl group, and C 5-8 A photosensitive resin composition substituted with at least one selected from the group consisting of cycloalkyl groups.

3. In paragraph 1, The photosensitive resin composition, wherein the above (A) acrylic-siloxane copolymer comprises a repeating unit produced by hydrolysis and condensation reaction of at least one alkoxysilane compound among the alkoxysilane compounds represented by the following chemical formulas 2-1 to 2-3: [Chemical Formula 2-1] Si(R 21 )2(OR 22 )2 [Chemical Formula 2-2] Si(R 23 )(OR 24 )3 [Chemical Formula 2-3] Si(OR 25 )4 In the above chemical formulas 2-1 to 2-3, R 21 , R 22 , R 23 , R 24 , and R 25 are each independently hydrogen, substituted or unsubstituted C 1-20 Alkyl group, substituted or unsubstituted C 2-20 Alkenyl group, substituted or unsubstituted C 3-20 Cycloalkyl group, substituted or unsubstituted C 6-20 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-20 It is a heteroaryl group, The above R 21 , R 22 , R 23 , R 24 , and R 25 C substituted by 1-20 Alkyl group, C 2-20 Alkenyl group, C 3-20 Cycloalkyl group, C 6-20 Aryl group, and C 5-20 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-10 Alkyl group, and C 5-10 It is substituted with at least one member selected from the group consisting of cycloalkyl groups.

4. In paragraph 3, In the above chemical formulas 2-1 to 2-3, The above R 21 , R 22 , R 23 , R 24 , and R 25 are each independently hydrogen, substituted or unsubstituted C 1-10 Alkyl group, substituted or unsubstituted C 2-10 Alkenyl group, or substituted or unsubstituted C 6-10 It is an aryl group, The above R 21 , R 22 , R 23 , R 24 , and R 25 C substituted by 1-10 Alkyl group, C 2-10 Alkenyl group and C 6-10 Aryl groups are each independently halogen, -NO2, -NH2, C 1-5 Alkyl group, and C 5-8 A photosensitive resin composition substituted with at least one selected from the group consisting of cycloalkyl groups.

5. In paragraph 1, A photosensitive resin composition, wherein the above (A) acrylic-siloxane copolymer comprises a repeating unit prepared by hydrolysis and condensation reaction of at least one compound selected from the group of compounds below: Phenylethoxydimethoxysilane, phenylmethoxydiethoxysilane, methylethoxydimethoxysilane, methylmethoxydiethoxysilane, phenylphenoxydimethoxysilane, phenylphenoxydiethoxysilane, phenylmethoxydimephenoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, phenyltripropoxysilane, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, tetrabutoxysilane, methylphenyldimethoxysilane, dimethyldimethoxysilane, diphenyldimethoxysilane, methylethyldiethoxysilane, vinyltrimethoxysilane, and vinyltriethoxysilane.

6. In paragraph 1, The above (A) acrylic-siloxane copolymer is a photosensitive resin composition further comprising a repeating unit derived from a compound represented by the following chemical formula 3: [Chemical Formula 3] In the above chemical formula 3, R 3 is hydrogen, substituted or unsubstituted C 1-20 Alkyl group, substituted or unsubstituted C 3-20 Cycloalkyl group, substituted or unsubstituted C 6-20 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-20 It is a heteroaryl group, The above substituted C 1-20 Alkyl group, C 3-20 Cycloalkyl group, C 6-20 Aryl group, and C 5-20 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-10 Alkyl group, and C 5-10 It may be substituted with at least one selected from the group consisting of cycloalkyl groups; Y is -OH, -COOH, epoxy group, or C 1-5 is an alkyl group; and n is an integer from 0 to 10.

7. In paragraph 6, In the above chemical formula 3, The above R 3 is hydrogen, substituted or unsubstituted C 1-10 Alkyl group, substituted or unsubstituted C 5-10 Cycloalkyl group, substituted or unsubstituted C 6-10 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-10 It is a heteroaryl group, The above R 3 C substituted by 1-10 Alkyl group, C 5-10 Cycloalkyl group, C 6-10 Aryl group, and C 5-10 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-5 Alkyl group, and C 5-8 A photosensitive resin composition substituted with at least one selected from the group consisting of cycloalkyl groups.

8. In paragraph 6, A photosensitive resin composition in which the repeating unit derived from the compound represented by the above chemical formula 3 is at least one selected from the following group: , , , , , , and .

9. In paragraph 1, The above (A) acrylic-siloxane copolymer is a photosensitive resin composition further comprising a repeating unit derived from a compound represented by the following chemical formula 4: [Chemical Formula 4] In the above chemical formula 4, R 4 is hydrogen, substituted or unsubstituted C 1-20 Alkyl group, substituted or unsubstituted C 3-20 Cycloalkyl group, substituted or unsubstituted C 6-20 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-20 It is a heteroaryl group, The above substituted C 1-20 Alkyl group, C 3-20 Cycloalkyl group, C 6-20 Aryl group, and C 5-20 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-10 Alkyl group, and C 5-10 It may be substituted with at least one selected from the group consisting of cycloalkyl groups; and m is an integer from 0 to 10.

10. In paragraph 9, In the above chemical formula 4, The above R 4 is hydrogen, substituted or unsubstituted C 1-10 Alkyl group, substituted or unsubstituted C 5-10 Cycloalkyl group, substituted or unsubstituted C 6-10 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-10 It is a heteroaryl group, The above R 4 C substituted by 1-10 Alkyl group, C 5-10 Cycloalkyl group, C 6-10 Aryl group, and C 5-10 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-5 Alkyl group, and C 5-8 A photosensitive resin composition substituted with at least one selected from the group consisting of cycloalkyl groups.

11. In paragraph 1, The photosensitive resin composition further comprises (D) a siloxane polymer.

12. In paragraph 11, The photosensitive resin composition, wherein the above (D) siloxane polymer comprises a repeating unit produced by hydrolysis and condensation reaction of at least one alkoxysilane compound represented by the following chemical formulae 5-1 to 5-3: [Chemical Formula 5-1] Si(R 51 )2(OR 52 )2 [Chemical Formula 5-2] Si(R 53 )(OR 54 )3 [Chemical Formula 5-3] Si(OR 55 )4 In the above chemical formulas 5-1 to 5-3, R 51 , R 52 , R 53 , R 54 , and R 55 are each independently hydrogen, substituted or unsubstituted C 1-20 Alkyl group, substituted or unsubstituted C 2-20 Alkenyl group, substituted or unsubstituted C 3-20 Cycloalkyl group, substituted or unsubstituted C 6-20 An aryl group, or a substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S. 5-20 It is a heteroaryl group, The above R 51 , R 52 , R 53 , R 54 , and R 55 C substituted by 1-20 Alkyl group, C 2-20 Alkenyl group, C 3-20 Cycloalkyl group, C 6-20 Aryl group, and C 5-20 Heteroaryl groups are each independently halogen, -NO2, -NH2, C 1-10 Alkyl group, and C 5-10 It is substituted with at least one member selected from the group consisting of cycloalkyl groups.

13. In paragraph 12, In the above chemical formulas 5-1 to 5-3, The above R 51 , R 52 , R 53 , R 54 , and R 55 are each independently hydrogen, substituted or unsubstituted C 1-10 Alkyl group, substituted or unsubstituted C 2-10 Alkenyl group, or substituted or unsubstituted C 6-10 It is an aryl group, The above R 51 , R 52 , R 53 , R 54 , and R 55 C substituted by 1-10 Alkyl group, C 2-10 Alkenyl group and C 6-10 Aryl groups are each independently halogen, -NO2, -NH2, C 1-5 Alkyl group, and C 5-8 A photosensitive resin composition substituted with at least one selected from the group consisting of cycloalkyl groups.

14. In paragraph 11, A photosensitive resin composition, wherein the above (D) siloxane polymer comprises a repeating unit prepared by hydrolysis and condensation reaction of at least one compound selected from the group of compounds below: Phenylethoxydimethoxysilane, phenylmethoxydiethoxysilane, methylethoxydimethoxysilane, methylmethoxydiethoxysilane, phenylphenoxydimethoxysilane, phenylphenoxydiethoxysilane, phenylmethoxydimephenoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, phenyltripropoxysilane, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, tetrabutoxysilane, methylphenyldimethoxysilane, dimethyldimethoxysilane, diphenyldimethoxysilane, methylethyldiethoxysilane, vinyltrimethoxysilane, and vinyltriethoxysilane.

15. In paragraph 1, In the above chemical formula 1, X is -L 1 -Si(R 11 ) x1 (OR 12 ) x2 And, Above L 1 Silver substituted or unsubstituted C 1-10 A combination of one or more substituents selected from the group consisting of alkylene groups, -COO-, and -O-, Above L 1 C substituted by 1-10 A photosensitive resin composition, wherein an alkylene group is substituted with at least one selected from the group consisting of halogen, -NO2, -NH2, and -OH.

16. In paragraph 1, A photosensitive resin composition wherein the molecular weight of the above (A) acrylic-siloxane copolymer is 1,000 g / mol to 100,000 g / mol.

17. In paragraph 11, A photosensitive resin composition, wherein the molecular weight of the above (D) siloxane polymer is 1,000 g / mol to 50,000 g / mol.

18. A photoresist film manufactured using a photosensitive resin composition according to any one of claims 1 to 17.

19. A substrate protective film manufactured using a photosensitive resin composition according to any one of claims 1 to 17.

20. A step of manufacturing a photoresist film by applying a photosensitive resin composition according to any one of claims 1 to 17 onto a substrate; A step of exposing the above photoresist film; and A method for forming a pattern, comprising a step of developing the above-mentioned exposed photoresist film using a developer.

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