Novel compounds and photosensitive resin compositions comprising the same

Abstract

The present invention relates to a compound represented by Chemical Formula 1, which is a novel compound capable of being used as a polymerizable compound of a photosensitive resin composition that can ensure a high refractive index while having excellent reliability such as no generation of residues, and a photosensitive resin composition comprising the same.

Description

Technical Field

[0001] This invention relates to a novel compound and a photosensitive resin composition comprising the same. Background Technology

[0002] Photosensitive resin compositions are essential materials for color filters, liquid crystal display materials, organic light-emitting devices, displays, etc., and are used to form various cured patterns such as photoresists, insulating films, protective films, black matrices, and columnar spacers. Specifically, photosensitive resin compositions are selectively exposed and developed through photolithography processes to form desired patterns.

[0003] Specifically, the patterning of the photosensitive resin composition relies on photolithography, which involves polarity changes and cross-linking reactions of polymers caused by photoreaction. In particular, the formation of the aforementioned patterns utilizes the change in solubility in solvents such as alkaline aqueous solutions after exposure.

[0004] For photosensitive resin compositions, ensuring resistance to heat treatment, chemical etching, and gas etching processes used in the manufacturing process is crucial. In particular, recently, in the application of improving the light efficiency of displays, not only are high transmittance and high refractive properties required, but also high reliability of the patterns formed by photolithography processes.

[0005] Korean Patent Publication No. 10-2024-0026933 discloses a high-refractive-index photosensitive composition containing an epoxy group photopolymerizable compound, but it has the limitation of producing residues during pattern formation, which cannot improve reliability.

[0006] Existing technical documents

[0007] Patent documents

[0008] Patent Document 1: Korean Patent Publication No. 10-2024-0026933 Summary of the Invention

[0009] The technical problem to be solved

[0010] To address the problems of the prior art, one object of the present invention is to provide a compound having the characteristic of an aromatic ring structure containing a carboxyl group, thereby enabling it to be used as a polymerizable compound in photosensitive resin compositions that can ensure high refractive index while exhibiting excellent reliability such as no residue generation.

[0011] Furthermore, another object of the present invention is to provide a photosensitive resin composition comprising the said compound.

[0012] However, the problems that this invention aims to solve are not limited to those mentioned above, and those skilled in the art will clearly understand from the following description other problems not mentioned.

[0013] Technical solution

[0014] To achieve the above objectives, the present invention provides a compound represented by the following chemical formula 1:

[0015] [Chemical Formula 1]

[0016]

[0017] In the above chemical formula 1,

[0018] R1 is an independent (meth)acrylate group with 4 to 20 carbon atoms, consisting of one or more -CH2- groups substituted or unsubstituted with -NH-, -O-, or -S-.

[0019] X is an organic group consisting of a hydroxyl group, one or more -CH2- groups substituted or unsubstituted with -NH-, -O- or -S-, having 4 to 20 carbon atoms, or an organic group containing a sulfur (S) atom and an aromatic ring group.

[0020] Y is a tetravalent aromatic ring group.

[0021] Except for cases where X does not contain any hydroxyl groups.

[0022] The Y can be a tetravalent aromatic cyclic group with 6 to 30 carbon atoms.

[0023] The Y may contain sulfur (S) atoms within the structure.

[0024] The compound represented by the above chemical formula 1 can be any one selected from the compounds represented by the following chemical formulas 1-1 and 1-2:

[0025] [Chemical Formula 1-1]

[0026]

[0027] [Chemical Formula 1-2]

[0028]

[0029] In the above chemical formulas 1-1 and 1-2,

[0030] R1 is an independent (meth)acrylate group with 4 to 20 carbon atoms, consisting of one or more -CH2- groups substituted or unsubstituted with -NH-, -O-, or -S-.

[0031] X is an organic group consisting of a hydroxyl group, one or more -CH2- groups substituted or unsubstituted with -NH-, -O- or -S-, having 4 to 20 carbon atoms, or an organic group containing a sulfur (S) atom and an aromatic ring group.

[0032] Except for cases where X does not contain any hydroxyl groups.

[0033] The compound represented by chemical formula 1 above can be any one selected from the compounds represented by chemical formulas 2-1 to 2-10 below:

[0034] [Chemical Formula 2-1]

[0035]

[0036] [Chemical Formula 2-2]

[0037]

[0038] [Chemical Formula 2-3]

[0039]

[0040] [Chemical Formula 2-4]

[0041]

[0042] [Chemical Formula 2-5]

[0043]

[0044] [Chemical Formula 2-6]

[0045]

[0046] [Chemical Formula 2-7]

[0047]

[0048] [Chemical Formula 2-8]

[0049]

[0050] [Chemical Formula 2-9]

[0051]

[0052] [Chemical Formula 2-10]

[0053] .

[0054] Furthermore, the present invention provides a photosensitive resin composition comprising one or more of the above-mentioned compounds, and comprising an alkali-soluble resin, a photopolymerization initiator, and a solvent.

[0055] Furthermore, the present invention provides a pattern comprising a cured product of the above-described photosensitive resin composition.

[0056] The refractive index of the pattern at a wavelength of 550 nm can be greater than 1.6.

[0057] Furthermore, the present invention provides a display device comprising the above-described pattern.

[0058] The effects of the invention

[0059] Based on the aromatic ring structure containing a carboxyl group, the present invention can provide a compound that can be used as a polymerizable compound in a photosensitive resin composition that can ensure a high refractive index while having excellent reliability such as no residue.

[0060] Furthermore, the present invention can provide a photosensitive resin composition comprising the above-mentioned compounds. Detailed Implementation

[0061] This invention relates to a compound represented by chemical formula 1 and a photosensitive resin composition comprising the same.

[0062] The present invention has experimentally demonstrated that it can provide a compound having a specific structure, specifically having a structure in which 2 to 3 carboxyl groups in an aromatic ring containing 4 carboxyl groups are bonded to a photoreactive (meth)acrylate group, thereby enabling it to be used as a polymerizable compound in photosensitive resin compositions that can ensure high refractive index while having excellent reliability such as no residue generation, and the present invention is thus completed.

[0063] The present invention will now be described in more detail.

[0064] In this invention, the total weight of solid components in the photosensitive resin composition refers to the total weight of all components in the photosensitive resin composition except for the solvent.

[0065] As used in this specification, “(meth)acrylate” includes and refers to acrylates and / or methacrylates.

[0066] The terms “comprises” and / or “comprising” as used in this specification are used to mean that the presence or addition of more than one other constituent element besides the mentioned constituent element is not excluded.

[0067] <Novel Compounds>

[0068] This invention provides a novel compound, specifically, the novel compound comprising the compound represented by the following chemical formula 1:

[0069] [Chemical Formula 1]

[0070]

[0071] In the above chemical formula 1,

[0072] R1 is an independent (meth)acrylate group with 4 to 20 carbon atoms, consisting of one or more -CH2- groups substituted or unsubstituted with -NH-, -O-, or -S-.

[0073] X is an organic group consisting of a hydroxyl group, one or more -CH2- groups substituted or unsubstituted with -NH-, -O- or -S-, having 4 to 20 carbon atoms, or an organic group containing a sulfur (S) atom and an aromatic ring group.

[0074] Y is a tetravalent aromatic ring group.

[0075] Except for cases where X does not contain any hydroxyl groups.

[0076] More specifically, the above chemical formula 1 can be any of the following chemical formulas 1-1 to 1-2:

[0077] [Chemical Formula 1-1]

[0078]

[0079] [Chemical Formula 1-2]

[0080]

[0081] In the above chemical formulas 1-1 to 1-2,

[0082] R1 is an independent (meth)acrylate group with 4 to 20 carbon atoms, consisting of one or more -CH2- groups substituted or unsubstituted with -NH-, -O-, or -S-.

[0083] X is an organic group consisting of a hydroxyl group, one or more -CH2- groups substituted or unsubstituted with -NH-, -O- or -S-, having 4 to 20 carbon atoms, or an organic group containing a sulfur (S) atom and an aromatic ring group.

[0084] Except for cases where X does not contain any hydroxyl groups.

[0085] In one embodiment of the invention, R1 can be a linear and / or branched (meth)acrylate group with 4 to 40 carbon atoms, preferably a linear and / or branched (meth)acrylate group with 4 to 20 carbon atoms, but not limited thereto. R1 contains 1 to 3 (meth)acrylate groups, thus exhibiting faster photoreactive properties upon light irradiation compared to compounds containing epoxy groups. When the compound is used as a polymerizable compound in a photosensitive resin composition, it has the advantage of not producing residue; therefore, it is preferable to include photoreactive (meth)acrylate groups in the structure.

[0086] In one embodiment of the present invention, R1 can be a straight-chain and / or branched (meth)acrylate group with one or more -CH2- groups replaced by -NH-, -O- or -S-. From the perspective of high electron density and strong polarity, which can improve the refractive index and thus ensure high refractive properties, it is preferred to be replaced by -S-.

[0087] In one embodiment of the invention, X may be a linear and / or branched (meth)acrylate group with 4 to 40 carbon atoms, preferably a linear and / or branched (meth)acrylate group with 4 to 20 carbon atoms, but is not limited thereto. X contains 1 to 3 (meth)acrylate groups, thereby exhibiting photoreactive properties with a faster curing speed upon light irradiation compared to compounds containing epoxy groups. Furthermore, when the compound is used as a polymerizable compound in a photosensitive resin composition, it has the advantage of not producing residue; therefore, it is preferable to include photoreactive (meth)acrylate groups in the structure.

[0088] In one embodiment of the present invention, X can be a straight-chain and / or branched (meth)acrylate group with one or more -CH2- groups replaced by -NH-, -O- or -S-. From the perspective of high electron density and strong polarity, which can improve the refractive index and thus ensure high refractive properties, it is preferred to be replaced by -S-.

[0089] In one embodiment of the present invention, X can be an organic group containing a sulfur (S) atom and an aromatic ring group, preferably including thiophene, 2-naphthiophene, 5-mercapto-1-phenyl-1H-tetrazole, etc., but not limited thereto. Since X simultaneously contains a sulfur atom and an aromatic ring group, it has high electron density and strong polarity, which can improve the refractive index and thus ensure high refractive properties. Therefore, it is preferable to include an organic compound containing a sulfur (S) atom and an aromatic ring group in its structure.

[0090] In one embodiment of the present invention, when forming a pattern using a photosensitive resin composition, from the perspective of achieving fast development speed and excellent adhesion, it is necessary to ensure a structure in which at least one carboxyl group is bonded to the Y group. Therefore, except for the case where none of the X groups contain hydroxyl groups, and the case where all X groups are (meth)acrylate groups and / or organic compounds containing sulfur (S) atoms and aromatic ring groups, it is not preferred. When all X groups are (meth)acrylate groups and / or organic compounds containing sulfur (S) atoms and aromatic ring groups, it may lead to a decrease in developability in alkaline developing solutions, resulting in residue problems.

[0091] In one embodiment of the present invention, Y can be a tetravalent aromatic cyclic group, specifically a tetravalent aromatic cyclic group containing one or more aromatic rings, preferably a tetravalent aromatic cyclic group with 6 to 30 carbon atoms. The tetravalent aromatic cyclic group can be an aromatic tetracarboxylic acid residue derived from an aromatic tetracarboxylic acid dianhydride. The aromatic tetracarboxylic acid dianhydride is not particularly limited as long as it achieves the purpose of the present invention, and known substances can be used.

[0092] Examples of aromatic tetracarboxylic dianhydrides include: pyromellitic dianhydride, 3,3',4,4'-benzophenone tetracarboxylic dianhydride, 2,2',3,3'-benzophenone tetracarboxylic dianhydride, 2,3,3',4'-benzophenone tetracarboxylic dianhydride, naphthalene-2,3,6,7-tetracarboxylic dianhydride, naphthalene-1,2,5,6-tetracarboxylic dianhydride, naphthalene-1,2,4,5-tetracarboxylic dianhydride, naphthalene-1,4,5,8-tetracarboxylic dianhydride, naphthalene-1,2,6,7-tetracarboxylic dianhydride, 4,8-dimethyl-1,2,3,5,6,7-hexahydronaphthalene-1,2,5,6-tetracarboxylic dianhydride, 4,8-dimethyl-1,2,3,5,6,7-hexahydronaphthalene-2,3,6,7-tetracarboxylic dianhydride, 2,6-dichloro Naphthalene-1,4,5,8-tetracarboxylic acid dianhydride, 2,7-dichloronaphthalene-1,4,5,8-tetracarboxylic acid dianhydride, 2,3,6,7-tetrachloronaphthalene-1,4,5,8-tetracarboxylic acid dianhydride, 1,4,5,8-tetrachloronaphthalene-2,3,6,7-tetracarboxylic acid dianhydride, 3,3',4,4'-biphenyltetracarboxylic acid dianhydride, 2,2',3,3'-biphenyltetracarboxylic acid dianhydride, 2,3,3',4'-biphenyltetracarboxylic acid dianhydride, 3,3",4,4"-p-terphenyltetracarboxylic acid dianhydride, 2,2",3,3"-p-terphenyltetracarboxylic acid dianhydride, 2,3,3",4"-p-terphenyltetracarboxylic acid dianhydride, 2,2-bis(2,3-dicarboxyphenyl)propane dianhydride, 2,2-bis(3,4-dicarboxyphenyl)propane dianhydride, bis( 2,3-Dicarboxyphenyl) ether dianhydride, bis(2,3-dicarboxyphenyl)methane dianhydride, bis(3,4-dicarboxyphenyl)methane dianhydride, bis(2,3-dicarboxyphenyl) sulfone dianhydride, bis(3,4-dicarboxyphenyl) sulfone dianhydride, 1,1-bis(2,3-dicarboxyphenyl)ethane dianhydride, 1,1-bis(3,4-dicarboxyphenyl)ethane dianhydride, perylene-2,3,8,9-tetracarboxylic acid dianhydride, perylene-3,4,9,10-tetracarboxylic acid dianhydride, perylene-4,5,10,11-tetracarboxylic acid dianhydride, perylene-5,6,11,12-tetracarboxylic acid dianhydride, phenanthrene-1,2,7,8-tetracarboxylic acid dianhydride, phenanthrene-1,2,6,7-tetracarboxylic acid dianhydride, phenanthrene-1,2,9,10-tetracarboxylic acid dianhydride, cyclopentane-1,2, 3,4-Tetracarboxylic dianhydride, pyrazine-2,3,5,6-tetracarboxylic dianhydride, pyrrolidine-2,3,4,5-tetracarboxylic dianhydride, thiophene-2,3,4,5-tetracarboxylic dianhydride, 4,4'-oxophthalic dianhydride, 3,3',4,4'-diphenyl sulfone tetracarboxylic dianhydride, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, etc., are preferred from the perspective of high electron density and strong polarity to ensure high refractive properties. Other preferred options include pyromellitic dianhydride, 3,3',4,4'-benzophenone tetracarboxylic dianhydride, 3,3',4,4'-biphenyl tetracarboxylic dianhydride, naphthalene-1,4,5,8-tetracarboxylic dianhydride, perylene-3,4,9,10-tetracarboxylic dianhydride, 4,4'-oxophthalic dianhydride, 3,3',4,4'-bis(3,4-dicarboxyphenyl)fluorene dianhydride, etc.4'-Diphenylsulfone tetracarboxylic acid dianhydride, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride.

[0093] According to one embodiment of the present invention, the compound represented by chemical formula 1 above may be a compound represented by any one of chemical formulas 2-1 to 2-10 below, but is not limited thereto:

[0094] [Chemical Formula 2-1]

[0095]

[0096] [Chemical Formula 2-2]

[0097]

[0098] [Chemical Formula 2-3]

[0099]

[0100] [Chemical Formula 2-4]

[0101]

[0102] [Chemical Formula 2-5]

[0103]

[0104] [Chemical Formula 2-6]

[0105]

[0106] [Chemical Formula 2-7]

[0107]

[0108] [Chemical Formula 2-8]

[0109]

[0110] [Chemical Formula 2-9]

[0111]

[0112] [Chemical Formula 2-10]

[0113] .

[0114] The aforementioned novel compounds can be included in the photosensitive resin composition, and when included, they can be used as polymerizable compounds. In particular, from the perspective of ensuring a high refractive index for the pattern, it is preferable to include the aforementioned novel compounds in the manufacture of the photosensitive resin composition.

[0115] When the novel compound is included in the photosensitive resin composition, the content of the novel compound relative to the total weight of the solid components in the photosensitive resin composition can be 5 to 70% by weight, preferably 10 to 60% by weight, but is not limited thereto. When the content of the novel compound is within the above range, it is preferred from the perspective of developability in alkaline developing solution and pattern formation.

[0116] <Photosensitive Resin Composition>

[0117] The present invention provides a photosensitive resin composition comprising the above-mentioned novel compounds, wherein the photosensitive resin composition may further comprise an alkali-soluble resin, a photopolymerization initiator and a solvent, and in addition to the above-mentioned novel compounds, may further comprise a polymerizable compound.

[0118] Alkali-soluble resins

[0119] The alkali-soluble resin of the present invention can be selected from resins known in the art without particular limitation, as long as it has reactivity and alkali solubility under the action of light or heat, functions as a dispersion medium for solid components including colorants, and functions as a binder resin.

[0120] Specifically, the alkali-soluble resin is preferably a copolymer of a monomer containing an unsaturated carboxyl group and other monomers that can be copolymerized with it.

[0121] Examples of monomers containing unsaturated carboxyl groups include unsaturated carboxylic acids, such as unsaturated monocarboxylic acids, unsaturated dicarboxylic acids, and unsaturated polycarboxylic acids, which have one or more carboxyl groups in their molecules.

[0122] Examples of unsaturated monocarboxylic acids include acrylic acid, methacrylic acid, crotonic acid, α-chloroacrylic acid, and cinnamic acid.

[0123] Examples of unsaturated dicarboxylic acids mentioned above include maleic acid, fumaric acid, itaconic acid, citraconic acid, and medoconic acid.

[0124] The aforementioned unsaturated polycarboxylic acids can be acid anhydrides, specifically maleic anhydride, itaconic anhydride, and citraconic anhydride. Furthermore, these unsaturated polycarboxylic acids can be their mono(2-methacryloyloxyalkyl) esters, such as succinate mono(2-acryloyloxyethyl) ester, phthalate mono(2-acryloyloxyethyl) ester, and phthalic acid mono(2-methacryloyloxyethyl) ester. These unsaturated polycarboxylic acids can also be mono(meth)acrylates of their dicarboxylic acid polymers, such as ω-carboxylated polycaprolactone monoacrylate and ω-carboxylated polycaprolactone monomethacrylate. The aforementioned carboxyl-containing monomers can be used individually or in combination of two or more.

[0125] Other monomers that can copolymerize with the aforementioned carboxyl-containing monomers include, for example, 3,4-epoxytricyclo[5.2.1.0²]. ,6 ] Decane-9-yl acrylate, 3,4-epoxy tricyclic [5.2.1.0² ,6Epoxy (meth)acrylate compounds such as decane-8-yl acrylate, glycidyl methacrylate, and 4-hydroxybutyl acrylate glycidyl ether; aromatic vinyl compounds such as styrene, α-methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinylbenzyl methyl ether, m-vinylbenzyl methyl ether, p-vinylbenzyl methyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, and indene; methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, isopropyl acrylate, and methyl... Isopropyl acrylate, n-butyl acrylate, n-butyl methacrylate, isobutyl acrylate, isobutyl methacrylate, sec-butyl acrylate, sec-butyl methacrylate, tert-butyl acrylate, tert-butyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate, 2-hydroxybutyl acrylate, 2-hydroxybutyl methacrylate, 3-hydroxybutyl methacrylate, 3-hydroxybutyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, allyl acrylate, allyl methacrylate, benzyl acrylate, benzyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate Hexyl acrylate, phenyl acrylate, phenyl methacrylate, 2-methoxyethyl acrylate, 2-methoxyethyl methacrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate, methoxydiethylene glycol acrylate, methoxydiethylene glycol methacrylate, methoxytriethylene glycol acrylate, methoxytriethylene glycol methacrylate, methoxypropylene glycol acrylate, methoxypropylene glycol methacrylate, methoxydipropylene glycol methacrylate, isobornyl acrylate, isobornyl methacrylate, dicyclopentenyl acrylate, dicyclopentenyl methacrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-hydroxy-3-phenoxypropyl methacrylate, glyceryl monoacrylate Unsaturated carboxylic acid esters such as oleic acid esters and glyceryl monomethacrylate; unsaturated carboxylic acid aminoalkyl esters such as 2-aminoethyl acrylate, 2-aminoethyl methacrylate, 2-dimethylaminoethyl acrylate, 2-aminopropyl methacrylate, 2-dimethylaminopropyl acrylate, 2-dimethylaminopropyl methacrylate, 3-aminopropyl acrylate, 3-aminopropyl methacrylate, 3-dimethylaminopropyl methacrylate; unsaturated carboxylic acid glycidyl esters such as glycidyl acrylate and glycidyl methacrylate; and carboxylic acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate, and vinyl benzoate.Unsaturated ethers such as vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether; cyanide vinyl compounds such as acrylonitrile, methacrylonitrile, α-chloroacrylonitrile, and vinylidene cyanide; unsaturated amides such as acrylamide, methacrylamide, α-chloroacrylonitrile, N-2-hydroxyethylacrylonitrile, and N-2-hydroxyethylmethacrylonitrile; unsaturated imides such as maleimide, N-phenylmaleimide, and N-cyclohexylmaleimide; aliphatic conjugated dienes such as 1,3-butadiene, isoprene, and chloroprene; and macromonomers whose polymer chains of polystyrene, polymethyl acrylate, polymethyl methacrylate, polybutyl acrylate, polybutyl methacrylate, and polysiloxane have monoacryloyl or monomethacryloyl groups at the end. These monomers can be used individually or in combination of two or more.

[0126] In one embodiment of the present invention, the alkali-soluble resin may be a copolymer represented by the following chemical formula 3:

[0127] [Chemical Formula 3]

[0128]

[0129] In the above chemical formula 3,

[0130] A is the base represented by the following chemical formula 4.

[0131] B represents the residues remaining after removing the carboxylic anhydride group (-CO-O-CO-) from the dicarboxylic anhydrides contained in maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylmethylenetetrahydrophthalic anhydride, chlorogenic anhydride, methyltetrahydrophthalic anhydride, and glutaric anhydride.

[0132] Z represents the residue remaining after removing two carboxylic anhydride groups from tetracarboxylic anhydrides such as pyromellitic tetracarboxylic anhydride, benzophenone tetracarboxylic dianhydride, biphenyl tetracarboxylic dianhydride, and diphenyl ether tetracarboxylic dianhydride.

[0133] [Chemical Formula 4]

[0134] .

[0135] In the above chemical formula 4,

[0136] * indicates a bonding bond.

[0137] The acid value of the aforementioned alkali-soluble resin can be from 10 mg·KOH / g to 150 mg·KOH / g. This acid value is determined as the amount (mg) of potassium hydroxide required to neutralize 1 g of the polymer, and is typically obtained by titration using an aqueous potassium hydroxide solution. If the acid value is within the above range, the solubility in the developer is improved, making the non-exposed areas easier to dissolve and increasing sensitivity. As a result, the pattern in the exposed areas remains during development, improving the film remaining ratio, which is therefore preferable.

[0138] For the aforementioned alkali-soluble resin, the converted weight-average molecular weight (hereinafter referred to as "weight-average molecular weight") of polystyrene, determined by gel permeation chromatography (GPC; with tetrahydrofuran as the elution solvent), can be from 3,000 to 200,000, preferably from 5,000 to 100,000. If the weight-average molecular weight is within the above range, the hardness of the coating film is increased, resulting in a high film retention rate, and the solubility in the non-exposed areas of the developer is excellent, thus improving the resolution, which is therefore preferred.

[0139] The molecular weight distribution [weight-average molecular weight (Mw) / number-average molecular weight (Mn)] of the above-mentioned alkali-soluble resin can be from 1.5 to 6.0, preferably from 1.8 to 4.0. If the molecular weight distribution is within the above range, the developability is excellent, and therefore it is preferred.

[0140] The content of the alkali-soluble resin can be 1 to 70% by weight relative to the total weight of the solid components in the photosensitive resin composition, preferably 20 to 60% by weight. When the content of the alkali-soluble resin is within the above range, it is easy to obtain a photosensitive resin composition with excellent developability and a cured film with excellent chemical resistance, which is therefore preferred.

[0141] polymeric compounds

[0142] In addition to the compounds represented by the above-described chemical formula 1, the photosensitive resin compositions of the present invention may further comprise polymerizable compounds.

[0143] The aforementioned polymerizable compounds are those capable of polymerization by light. Any compound capable of polymerization by light and heat can be used without particular restriction, and can be any polymerizable compound known in the art. Specifically, monofunctional monomers, difunctional monomers, and other polyfunctional monomers can be used.

[0144] There are no particular limitations on the types of the aforementioned monofunctional monomers, difunctional monomers, and polyfunctional monomers. For example, as polyfunctional monomers, trimethylolpropane tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, propoxylated trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, ethoxylated dipentaerythritol hexa(meth)acrylate, propoxylated dipentaerythritol hexa(meth)acrylate, dipentaerythritol hexa(meth)acrylate, etc.

[0145] In one embodiment of the present invention, the polymeric compound may simultaneously include the compound represented by chemical formula 1 and the compound represented by chemical formula 1 in which X does not contain hydroxyl groups; by including the above-mentioned compound as a polymeric compound of the photosensitive resin composition, it is preferable that no residue is generated.

[0146] The content of the polymeric compound can be 5 to 70% by weight relative to the total weight of the solid components in the photosensitive resin composition, preferably 10 to 60% by weight. When the content of the polymeric compound is within the above range, it is preferable from the perspective of the strength or smoothness of the pixel portion.

[0147] Photopolymerization initiator

[0148] The photopolymerization initiator of the present invention is a compound used to initiate the polymerization of the compound represented by the above chemical formula 1. Photopolymerization initiators used in the art can be used without limitation as long as the purpose of the present invention is not impaired.

[0149] Specifically, the aforementioned photopolymerization initiators can be acetophenone-based, benzophenone-based, triazine-based, thioxanone-based, oxime-based, benzoin-based, and biimidazole-based compounds, which can be used individually or in combination of two or more. Examples of the aforementioned oxime compounds include o-ethoxycarbonyl-α-oxoimino-1-phenylpropane-1-one and 1-[4-(phenylthio)phenyl]-3-cyclohexyl-propane-1,2-dione-2-(o-acetyl oxime).

[0150] Commercially available photopolymerization initiators include, but are not limited to, PBG-327, PBG-329, PBG-305 (manufactured by TRONLY), NCI-831E (manufactured by ADEKA), OXE-01, OXE-02 (manufactured by Ciba) and N-1919 (manufactured by ADEKA).

[0151] The content of the photopolymerization initiator relative to the total weight of the solid components in the photosensitive resin composition can be from 0.01 to 10% by weight, preferably from 0.1 to 5% by weight. This range is set considering the photopolymerization rate of the photopolymerizable compound and the physical properties of the final coating film. When the content of the photopolymerization initiator is below this range, the polymerization rate may be low, resulting in a longer overall process time. When the content is above this range, over-reaction may occur, leading to a decrease in the physical properties of the coating film after the cross-linking reaction. Therefore, the content is preferably within the above range.

[0152] solvent

[0153] The solvent of the present invention can be any organic solvent commonly used in the art without particular limitation. Examples of such solvents include ethers, acetates, aromatic hydrocarbons, ketones, alcohols, and esters, and more than one of them can be used, but the invention is not limited thereto.

[0154] For example, examples 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; propylene glycol ethers such as propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, propylene glycol dimethyl ether, dipropylene glycol dimethyl ether, propylene glycol diethyl ether, and dipropylene glycol diethyl ether; and methyl cellosolve acetate and ethyl cellosolve acetate. Ethylene glycol alkyl ether acetates; propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate, and methoxypentyl acetate, etc., alkylene glycol alkyl ether acetates; aromatic hydrocarbons such as benzene, toluene, xylene, and mesitylene; ketones such as methyl ethyl ketone, acetone, methyl pentyl ketone, methyl isobutyl ketone, and cyclohexanone; alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerol; esters such as ethyl 3-ethoxypropionate and methyl 3-methoxypropionate; cyclic esters such as γ-butyrolactone, etc.

[0155] The solvents mentioned above are preferably alkylene glycol alkyl ether acetates, ketones, ethyl 3-ethoxypropionate, or methyl 3-methoxypropionate, etc.; more preferably, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, etc. These solvents can be used individually or in combination of two or more.

[0156] The content of the solvent relative to the total weight of the photosensitive resin composition can be 10 to 90% by weight, preferably 15 to 85% by weight, but is not limited thereto. When the content of the solvent is within the above range, the flatness during coating tends to improve, and is therefore preferred.

[0157] additive

[0158] The present invention may further include additives as needed. For example, it may further include one or more of the following: selected from other polymer compounds, curing agents, surfactants, adhesion promoters, antioxidants, ultraviolet absorbers and anti-gelling agents.

[0159] Specific examples of the other polymer compounds mentioned above include thermosetting resins such as epoxy resins and maleimide resins; thermoplastic resins such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ethers, polyfluoroalkyl acrylates, polyesters, and polyurethanes.

[0160] The aforementioned curing agents are used to achieve deep curing and improve mechanical strength. Specific examples include epoxy compounds, polyfunctional isocyanate compounds, melamine compounds, and oxetane compounds.

[0161] Among the aforementioned curing agents, specific examples of epoxy compounds include: bisphenol A type epoxy resin, hydrogenated bisphenol A type epoxy resin, bisphenol F type epoxy resin, hydrogenated bisphenol F type epoxy resin, phenolic varnish type epoxy resin, other aromatic epoxy resins, alicyclic epoxy resins, glycidyl ester resins, glycidyl amine resins, or brominated derivatives of these epoxy resins, aliphatic, alicyclic or aromatic epoxy compounds other than epoxy resins and their brominated derivatives, butadiene (co)polymer epoxides, isoprene (co)polymer epoxides, (meth)acrylate glycidyl ester (co)polymers, triglycidyl isocyanurate, etc.

[0162] Specific examples of oxetane compounds in the curing agent include carbonate oxetane, xylene oxetane, adipate oxetane, terephthalate oxetane, and cyclohexane dicarboxylic acid oxetane.

[0163] The aforementioned curing agent can be used in conjunction with a curing aid compound, which, together with the curing agent, enables the ring-opening polymerization of the epoxy groups of the epoxy compound and the oxetane skeleton of the oxetane compound. Examples of such curing aid compounds include polycarboxylic acids, polycarboxylic anhydrides, and acid-generating agents. Commercially available epoxy resin curing agents can be used as polycarboxylic anhydrides. Specific examples of such epoxy resin curing agents include ADEKA HARDENER EH-700 (trade name, manufactured by ADEKA Industries, Ltd.), RIKACID HH (trade name, manufactured by Shin Nippon Rikka Co., Ltd.), and MH-700 (trade name, manufactured by Shin Nippon Rikka Co., Ltd.). These curing agents can be used individually or in combination of two or more.

[0164] The surfactants described above can be used to further improve the film-forming properties of the photosensitive resin composition, and preferably silicone surfactants or fluorinated surfactants can be used.

[0165] For the aforementioned silicone-based surfactants, examples of commercially available products include: Dow Corning Toray Silicones' DC3PA, DC7PA, SH11PA, SH21PA, and SH-8400; and GE Toshiba Silicones' TSF-4440, TSF-4300, TSF-4445, TSF-4446, TSF-4460, and TSF-4452. For the aforementioned fluorinated surfactants, examples of commercially available products include MEGAFACE F-470, F-471, F-475, F-482, F-489, and F-554 (Dai Nippon Ink & Chemical Co., Ltd.), BM-1000 and BM-1100 (BM Chemie), and Fluorad FC-135 / FC-170C / FC-430 (Sumitomo 3M Co., Ltd.). These surfactants can be used individually or in combination of two or more.

[0166] The aforementioned adhesion promoter is an additive used to improve the coating and adhesion to the substrate, and may contain a silane coupling agent having reactive substituents selected from the group consisting of carboxyl, methacryloyl, isocyanate, epoxy, and combinations thereof.

[0167] Among the aforementioned adhesion promoters, specific examples of silane coupling agents include: trimethoxysilylbenzoic acid, γ-methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, γ-isocyanate propyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, etc.

[0168] Specific examples of the aforementioned antioxidants include 2,2'-thiobis(4-methyl-6-tert-butylphenol) and 2,6-di-tert-butyl-4-methylphenol.

[0169] Specific examples of the aforementioned ultraviolet absorbers include 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chlorobenzotriazole and alkoxybenzophenone.

[0170] Specific examples of the aforementioned anti-condensing agents include sodium polyacrylate.

[0171] For additives not listed in the above description, they may be appropriately added by those skilled in the art without impairing the effects of the present invention. For example, the amount of the above additives used relative to the total weight of the photosensitive resin composition may be 0.01 to 10% by weight, preferably 0.01 to 5% by weight, more preferably 0.02 to 3% by weight, but is not limited thereto.

[0172] <Pattern>

[0173] The present invention provides a pattern formed using the above-described photosensitive resin composition.

[0174] Apart from being formed by the above-described photosensitive resin composition, the pattern can be manufactured by methods known in the art. In the formation of a photocurable pattern, the pattern can be formed by a photolithography method that involves coating the above-described photosensitive resin composition onto a substrate and then exposing and developing the substrate.

[0175] According to an embodiment of the present invention, a conventional patterning process for forming a pattern by photolithography includes:

[0176] a) The step of coating a photosensitive resin composition onto a substrate;

[0177] b) The VCD (Vacuum Dry) step, in which the solvent is evaporated by depressurization;

[0178] c) Pre-drying step for drying solvent;

[0179] d) The step of aligning a photomask onto the obtained film and irradiating it with active light to cure the exposed portion;

[0180] e) Performing the developing process of dissolving the unexposed areas with an alkaline aqueous solution; and

[0181] f) Perform the drying and post-drying steps.

[0182] The aforementioned substrate uses a glass substrate or a polymer board. As a glass substrate, soda-lime glass, barium or strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, or quartz are particularly preferred. Furthermore, as a polymer board, examples include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, or polysulfone.

[0183] At this point, coating can be performed using wet coating methods with coating devices such as roller coaters, spin coaters, slot coaters, slot coaters (sometimes also called die coaters), and inkjet printers to achieve the desired thickness.

[0184] Pre-drying is carried out using heating methods such as ovens and hot plates. The heating temperature and time during pre-drying are appropriately selected according to the solvent used, and can be performed at low temperatures, such as 80 to 150°C or 80 to 100°C for 1 to 30 minutes.

[0185] Furthermore, the pre-baking followed by exposure is performed using an exposure machine, with exposure through a photomask, exposing only the portion corresponding to the pattern. The light used in this process can be, for example, visible light, ultraviolet light, X-rays, or electron beams.

[0186] Alkaline development after exposure is performed to remove the colored photosensitive resin composition from the unexposed areas, thereby forming a desired pattern. Suitable developing solutions for this alkaline development include, for example, aqueous solutions of alkali metal or alkaline earth metal carbonates. In particular, an alkaline aqueous solution containing 1 to 3% by weight of carbonates such as sodium carbonate, potassium carbonate, or lithium carbonate is used at a temperature range of 10 to 50°C, preferably 20 to 40°C, performed using a developing machine or an ultrasonic cleaner.

[0187] Post-baking is performed to improve the adhesion between the patterned film and the substrate. Post-baking can be performed at low temperatures, such as 80 to 150°C or 80 to 100°C, for 10 to 120 minutes via heat treatment. Like pre-baking, post-baking is performed using an oven, hot plate, etc.

[0188] The aforementioned pattern may be a photocurable pattern selected from the group consisting of array planarization film pattern, protective film pattern, insulating film pattern, photoresist pattern, black matrix pattern, columnar spacer pattern, black columnar spacer, colored photoresist pattern, pattern containing scatterers, and pattern containing quantum dots, but is not limited thereto.

[0189] <Display Device>

[0190] The present invention provides a display device including the above-described pattern.

[0191] In addition to having the above-described pattern, the display device may further include configurations known in the art.

[0192] Specifically, examples include liquid crystal displays (LCDs), organic EL displays (including organic EL displays, OLEDs and QLEDs), flexible displays, liquid crystal projectors, display devices for game consoles, display devices for portable terminals such as mobile phones, display devices for digital cameras, and navigation display devices, but are not limited to these.

[0193] The present invention will be described in more detail below through embodiments.

[0194] However, the following embodiments are used to illustrate the present invention in a more specific way, and the scope of the present invention is not limited by the following embodiments. The following embodiments can be appropriately modified and changed by those skilled in the art within the scope of the present invention.

[0195] In addition, unless otherwise specified, the "%" and "parts" used to indicate content in the following text are based on weight.

[0196] Synthesis Example 1: Preparation of Compounds (A-1)

[0197] Under a dry nitrogen stream, 4.58 g (0.01 mol) of 9,9-bis(3,4-dicarboxyphenyl)fluorene dihydride, 2.32 g (0.02 mol) of 2-hydroxyethyl acrylate, and 0.17 g (0.001 mol) of p-toluenesulfonic acid (p-TSA) were added. 100 mL of anhydrous tetrahydrofuran was then added, and the mixture was stirred at 70 °C for 5 hours. After the reaction was complete, the product was filtered under reduced pressure to remove all solvents and washed with a 20% methanol / water mixture, thereby synthesizing compound A-1 of chemical formula 2-1.

[0198] [Chemical Formula 2-1]

[0199]

[0200] The obtained product was confirmed by FT-IR and elemental analysis. FT-IR analysis of the product detected OH stretching vibrations (2500–3300 cm⁻¹) corresponding to the COOH groups formed during ring opening. -1 ) and the C=C stretching vibration of acrylate groups (1635 cm⁻¹) -1 The spectrum showed bands, but no corresponding symmetric or asymmetric C=O stretching vibrations (1851 cm⁻¹) were found corresponding to the anhydride group. -1 and 1778cm -1 The peaks indicated the formation of compound A-1. Furthermore, elemental analysis of the product confirmed the following: theoretical values: C 67.82%, H 4.38%, O 27.80%; actual values: C 67.71%, H 4.33%, O 27.96%.

[0201] Synthesis Example 2: Preparation of Compounds (A-2)

[0202] Under a dry nitrogen stream, 6.91 g (0.01 mol) of compound A-1 and 1.41 g (0.01 mol) of 2-isocyanatoethyl acrylate were added. 100 mL of anhydrous tetrahydrofuran was then added, and the mixture was stirred at 70 °C for 12 hours. After the reaction was complete, the product was filtered under reduced pressure to remove all solvents and washed with a 20% methanol / water mixture, thereby synthesizing compound A-2 of chemical formula 2-2.

[0203] [Chemical Formula 2-2]

[0204]

[0205] The product was confirmed by FT-IR and elemental analysis. FT-IR analysis of the product detected the C=O stretching vibration (1670 cm⁻¹) corresponding to the amide group. -1 The presence of the spectral band indicated the formation of compound A-2. Furthermore, elemental analysis of the product confirmed the following: theoretical values: C 67.09%, H 4.73%, N 1.78%, O 26.40%; actual values: C 67.01%, H 4.76%, N 1.82%, O 26.41%.

[0206] Synthesis Example 3: Preparation of Compounds (A-3)

[0207] Using glyceryl dimethacrylate instead of 2-hydroxyethyl acrylate in Synthesis Example 1, the same procedure as in Synthesis Example 1 was followed to synthesize compound A-3 of chemical formula 2-3.

[0208] [Chemical Formula 2-3]

[0209]

[0210] FT-IR analysis of the products showed the detection of OH stretching vibrations (2500–3300 cm⁻¹) corresponding to the COOH groups formed during ring opening. -1 ) and the C=C stretching vibration of acrylate groups (1638 cm⁻¹) -1 The spectrum showed bands, but no corresponding symmetric or asymmetric C=O stretching vibrations (1851 cm⁻¹) were found corresponding to the anhydride group. -1 and 1778cm -1 The peaks indicated the formation of compound A-3. Furthermore, elemental analysis of the product confirmed the following: theoretical values: C 71.99%, H 5.45%, O 22.56%; actual values: C 71.83%, H 5.51%, O 22.66%.

[0211] Synthesis Example 4: Preparation of Compounds (A-4)

[0212] Using pentaerythritol triacrylate instead of 2-hydroxyethyl acrylate in Synthesis Example 1, the same procedure as in Synthesis Example 1 was followed to synthesize compound A-4 of chemical formula 2-4.

[0213] [Chemical Formula 2-4]

[0214]

[0215] FT-IR analysis of the product detected OH stretching vibrations (2500~3300 cm⁻¹) corresponding to the COOH groups formed during ring opening. -1 ) and the C=C stretching vibration of acrylate groups (1640 cm⁻¹) -1 The spectrum showed bands, but no corresponding symmetric or asymmetric C=O stretching vibrations (1851 cm⁻¹) were found corresponding to the anhydride group. -1 and 1778cm -1 The peaks indicated the formation of compound A-4. Furthermore, elemental analysis of the product confirmed the following: theoretical values: C 71.39%, H 5.26%, O 23.36%; actual values: C 71.45%, H 5.23%, O 23.33%.

[0216] Synthesis Example 5: Preparation of Compounds (A-5)

[0217] The same procedure was performed as in Synthesis Example 1, except that 3,3',4,4'-diphenylsulfone tetracarboxylic acid dianhydride was used instead of 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride and pentaerythritol triacrylate was used instead of 2-hydroxyethyl acrylate, thereby synthesizing compound A-5 of chemical formula 2-5.

[0218] [Chemical Formula 2-5]

[0219]

[0220] FT-IR analysis of the product detected OH stretching vibrations (2500~3300 cm⁻¹) corresponding to the COOH groups formed during ring opening. -1 ) and the C=C stretching vibration of acrylate groups (1637 cm⁻¹) -1 The spectrum showed bands, but no corresponding symmetric or asymmetric C=O stretching vibrations (1851 cm⁻¹) were found corresponding to the anhydride group. -1 and 1778cm -1 The peaks indicated the formation of compound A-5. Furthermore, elemental analysis of the product confirmed the following: theoretical values: C 61.53%, H 4.93%, O 29.80%, S 3.73%; actual values: C 61.42%, H 4.95%, O 29.84%, S 3.77%.

[0221] Synthesis Example 6: Preparation of Compounds (A-6)

[0222] Under a dry nitrogen stream, 6.91 g (0.01 mol) of compound A-1, 1.10 g (0.01 mol) of thiophenol, and 2.26 g (0.013 mol) of methanesulfonic anhydride were added. 100 mL of anhydrous tetrahydrofuran was then added, and the mixture was stirred at 80 °C for 4 hours. After the reaction was complete, the product was filtered under reduced pressure to remove all solvents and washed with a 20% methanol / water mixture, thereby synthesizing compound A-6 of chemical formula 2-6.

[0223] [Chemical Formula 2-6]

[0224]

[0225] FT-IR analysis of the product detected OH stretching vibrations (2500~3300 cm⁻¹) corresponding to the COOH groups formed during ring opening. -1 ) and the C=C stretching vibration of acrylate groups (1638 cm⁻¹) -1 The spectrum showed bands, but no corresponding symmetric or asymmetric C=O stretching vibrations (1851 cm⁻¹) were found corresponding to the anhydride group. -1 and 1778cm -1 The peaks indicated the formation of compound A-6. Furthermore, elemental analysis of the product confirmed the following: theoretical values: C 69.04%, H 4.38%, O 22.48%, S 4.10%; actual values: C 68.86%, H 4.34%, O 22.62%, S 4.18%.

[0226] Synthesis Example 7: Preparation of Compounds (A-7)

[0227] Under a dry nitrogen stream, 6.91 g (0.01 mol) of compound A-1, 1.60 g (0.01 mol) of 2-naphthiophenol, and 2.26 g (0.013 mol) of methanesulfonic anhydride were added. 100 mL of anhydrous tetrahydrofuran was then added, and the mixture was stirred at 80 °C for 4 hours. After the reaction was complete, the product was filtered under reduced pressure to remove all solvents and washed with a 20% methanol / water mixture, thereby synthesizing compound A-7 of chemical formula 2-7.

[0228] [Chemical Formula 2-7]

[0229]

[0230] FT-IR analysis of the product detected OH stretching vibrations (2500~3300 cm⁻¹) corresponding to the COOH groups formed during ring opening. -1 ) and the C=C stretching vibration of acrylate groups (1644 cm⁻¹) -1 The spectrum showed bands, but no corresponding symmetric or asymmetric C=O stretching vibrations (1851 cm⁻¹) were found corresponding to the anhydride group. -1and 1778cm -1 The peaks indicated the formation of compound A-7. Furthermore, elemental analysis of the product confirmed the following: theoretical values: C 70.66%, H 4.36%, O 21.13%, S 3.85%; actual values: C 70.70%, H 4.32%, O 21.16%, S 3.82%.

[0231] Synthesis Example 8: Preparation of Compounds (A-8)

[0232] Under a dry nitrogen stream, 6.91 g (0.01 mol) of compound A-1, 1.78 g (0.01 mol) of 5-mercapto-1-phenyl-1H-tetrazole, and 2.26 g (0.013 mol) of methanesulfonic anhydride were added. 100 mL of anhydrous tetrahydrofuran was then added, and the mixture was stirred at 80 °C for 4 hours. After the reaction was complete, the product was filtered under reduced pressure to remove all solvents and washed with a 20% methanol / water mixture, thereby synthesizing compound A-8 of chemical formula 2-8.

[0233] [Chemical Formula 2-8]

[0234]

[0235] FT-IR analysis of the product detected OH stretching vibrations (2500~3300 cm⁻¹) corresponding to the COOH groups formed during ring opening. -1 ) and the C=C stretching vibration of acrylate groups (1643 cm⁻¹) -1 The spectrum showed bands, but no corresponding symmetric or asymmetric C=O stretching vibrations (1851 cm⁻¹) were found corresponding to the anhydride group. -1 and 1778cm -1 The peaks indicated the formation of compound A-8. Furthermore, elemental analysis of the product confirmed the following: theoretical values: C 64.94%, H 4.03%, N 6.58%, O 20.68%, S 3.77%; actual values: C 64.90%, H 4.00%, N 6.61%, O 20.68%, S 3.81%.

[0236] Synthesis Example 9: Preparation of Compounds (A'-3)

[0237] Under a dry nitrogen stream, 6.91 g (0.01 mol) of compound A-1 and 2.83 g (0.02 mol) of 2-isocyanatoethyl acrylate were added. 100 mL of anhydrous tetrahydrofuran was then added, and the mixture was stirred at 70 °C for 12 hours. After the reaction was complete, the product was filtered under reduced pressure to remove all solvents and washed with a 20% methanol / water mixture, thereby synthesizing compound A'-3 of chemical formula 2-11.

[0238] [Chemical Formula 2-11]

[0239]

[0240] FT-IR analysis of the product detected the C=O stretching vibration (1672 cm⁻¹) corresponding to the amide group. -1 The presence of the spectral band indicated the formation of compound A'-3. Furthermore, elemental analysis of the product confirmed the following: theoretical values: C 66.51%, H 5.01%, N 3.17%, O 25.31%; actual values: C 66.41%, H 5.04%, N 3.20%, O 25.35%.

[0241] Polymerization Example 1: Alkali-soluble resin (B)

[0242] After setting up a reflux condenser and thermometer in a three-necked flask, 42.5 g of 9,9-bisphenol fluorene was added, followed by 220 mL of 2-(chloromethyl)ethylene oxide. 100 mg of tetrabutylammonium bromide was added, and the mixture was stirred while the temperature was raised to 90 °C. After confirming that the unreacted content was below 0.3%, vacuum distillation was performed. The temperature was lowered to 30 °C, and dichloromethane was added, followed by slow addition of NaOH. After confirming that the product purity was above 96% by high-performance liquid chromatography (HPLC), 5% HCl was added dropwise to terminate the reaction. The reactants were extracted and separated into layers; the organic layer was washed with water until neutral. The organic layer was dried with MgSO4 and then concentrated by vacuum distillation using a rotary evaporator. Dichloromethane was added to the concentrated product, and the mixture was heated to 40 °C while stirring. Methanol was added, the solution temperature was lowered, and the mixture was stirred. The resulting solid was filtered and dried under vacuum at room temperature to obtain 52.7 g of a white solid powder. The obtained white solid powder was placed in a three-necked flask, and 27 g of thiophenol and 32 g of ethanol were added and stirred. 16.3 g of triethylamine was slowly added dropwise to the reaction solution. After the reaction was complete, the ethanol was removed by vacuum distillation. The organic matter was dissolved in dichloromethane and washed with water, and the dichloromethane was removed by vacuum distillation. An equal volume of PGMEA solvent was added to the three-necked flask to prepare a 50% solution, and the temperature was raised to 115 °C. 31.1 g of 3,3',4,4'-biphenyltetracarboxylic acid dianhydride was added dropwise at 115 °C, and the mixture was stirred for 6 hours while maintaining the temperature at 115 °C. 7.35 g of phthalic anhydride was added, and the reaction was terminated after further stirring for 2 hours. After cooling, an alkali-soluble resin (B) with a weight-average molecular weight of 5,000 g / mol was obtained.

[0243] Examples and Comparative Examples: Preparation of Photosensitive Resin Compositions

[0244] The photosensitive resin compositions of Examples 1 to 8 and Comparative Examples 1 to 3 were prepared according to the components and contents in Table 1 below.

[0245] [Table 1]

[0246]

[0247] - A-1 ~ A-8: Compounds from Synthetic Examples 1 ~ 8

[0248] - A'-1: TR-FR-301 (Tronly)

[0249] - A'-2: 2-Carboxyethyl acrylate (Merck)

[0250] - A'-3: Compound from Synthetic Example 9

[0251] - B: Alkali-soluble resin of Polymerization Example 1

[0252] - C: OXE-01 (Ciba)

[0253] - D: Propylene glycol monomethyl ether acetate (PGMEA)

[0254] Experimental Example

[0255] Using the photosensitive resin compositions manufactured in the above examples and comparative examples, after patterns were manufactured as described below, the refractive index, developability, residue and adhesion of the manufactured patterns were evaluated, and the results are recorded in Table 2 below.

[0256] Pattern making

[0257] A 5 × 5 cm glass substrate (Eagle 2000; manufactured by Corning Incorporated) was sequentially cleaned with neutral detergent, water, and alcohol, and then dried. The photosensitive resin compositions prepared in the above examples and comparative examples were spin-coated onto the glass substrate, and then pre-baked at 85°C for 120 seconds using a hot plate. After cooling the pre-baked substrate to room temperature, a test photomask with a line / pitch pattern of 1 μm to 50 μm was placed on it and heated at 50 mJ / cm². 2 The film was irradiated with light at an exposure level (based on 365 nm). After irradiation, it was developed in a 2.38% tetramethylammonium hydroxide (TMAH) aqueous solution for 100 seconds, washed with ultrapure water, and dried under nitrogen, thereby forming a pattern on the photosensitive resin composition film. The film was then post-baked at 90°C for 1 hour in an oven, resulting in a film thickness of 2 μm.

[0258] (1) Refractive index measurement

[0259] Except for the absence of a mask, following the above pattern manufacturing method, an ellipsometer (JA Woollam, M-2000) was used to measure the linear polarization of the exposed cured film at 25°C and 50%RH with incident angles of 65°, 70°, and 75°, within a wavelength range of 200nm to 1000nm. Using Complete EASE software, the measured linear polarization data (Ψ, Δ) were optimized and fitted using the Cauchy model of Equation 1 below to calculate the refractive index at 550nm wavelength, with an MSE below 70. The results are shown in Table 2 below according to the following criteria.

[0260] <Mathematical Formula 1>

[0261]

[0262] In the above mathematical formula 1, n(λ) is the refractive index at wavelength λ, λ is in the range of 300nm to 1800nm, and A, B and C are Cauchy parameters.

[0263] ◎:1.62 or above

[0264] ○: Below 1.62 and above 1.60

[0265] X: below 1.60

[0266] (2) Evaluation of radioactivity

[0267] For the embodiments and comparative examples, when the substrate was manufactured according to the above pattern manufacturing method, the time required for the non-exposed part to completely dissolve in the developer was measured in seconds for the development speed, and the results are shown in Table 2 below.

[0268] (3) Residue Evaluation

[0269] For the embodiments and comparative examples, the presence of residue around the pattern obtained by the above pattern manufacturing method was observed by optical microscope, and the evaluation was carried out according to the following evaluation criteria. The results are shown in Table 2 below.

[0270] ○: No residue

[0271] ×: There are residues.

[0272] (4) Fit evaluation

[0273] Except for the absence of a mask, the cured film formed by exposure was cross-cutting according to the above pattern manufacturing method. Adhesion was then confirmed using tape and evaluated according to ASTM D3359 standards. The results are shown in Table 2 below.

[0274] [Table 2]

[0275]

[0276] Based on the above experimental results, it can be confirmed that for Examples 1 to 8 containing the novel compound of the present invention, the refractive index at a wavelength of 550 nm is 1.6 or higher, exhibiting excellent refractive index, fast development speed in the developer, no residue generation, and good adhesion to the substrate.

[0277] In contrast, Comparative Examples 1 to 3, which do not contain the novel compound, produce residue around the pattern, have a lower refractive index compared to the Examples, and exhibit lower adhesion to the substrate.

[0278] In particular, Comparative Example 3, which contains a compound in Formula 1 where X are all acrylate groups, shows that the development speed is slow, residue is generated around the pattern, and the adhesion is low. Therefore, it can be confirmed that the novel compound of the present invention should contain a structure in Y that is bonded with at least one carboxyl group.

Claims

1. A compound represented by the following chemical formula 1: Chemical Formula 1 In the above chemical formula 1, R1 is an independent (meth)acrylate group with 4 to 20 carbon atoms, consisting of one or more -CH2- groups substituted or unsubstituted with -NH-, -O-, or -S-. X is an organic group consisting of a hydroxyl group, one or more -CH2- groups substituted or unsubstituted with -NH-, -O- or -S-, having 4 to 20 carbon atoms, or containing a sulfur atom and an aromatic ring group. Y is a tetravalent aromatic ring group. in, Except for cases where X does not contain hydroxyl groups.

2. The compound according to claim 1, wherein, The Y is a tetravalent aromatic cyclic group with 6 to 30 carbon atoms.

3. The compound according to claim 1, wherein, The Y contains sulfur atoms within the structure.

4. The compound according to claim 1, wherein, The compound represented by chemical formula 1 above is selected from any one of the compounds represented by chemical formulas 1-1 and 1-2 below: Chemical Formula 1-1 Chemical formula 1-2 In the above chemical formulas 1-1 and 1-2, R1 is an independent (meth)acrylate group with 4 to 20 carbon atoms, consisting of one or more -CH2- groups substituted or unsubstituted with -NH-, -O-, or -S-. X is an organic group consisting of a hydroxyl group, one or more -CH2- groups substituted or unsubstituted with -NH-, -O- or -S-, having 4 to 20 carbon atoms, or containing a sulfur atom and an aromatic ring group. Except for cases where X does not contain any hydroxyl groups.

5. The compound according to claim 1, wherein, The compound represented by chemical formula 1 above is selected from any one of the compounds represented by chemical formulas 2-1 to 2-10 below: Chemical formula 2-1 Chemical formula 2-2 Chemical formula 2-3 Chemical formula 2-4 Chemical formula 2-5 Chemical formula 2-6 Chemical formula 2-7 Chemical formula 2-8 Chemical formula 2-9 Chemical formula 2-10 。 6. A photosensitive resin composition comprising one or more compounds according to any one of claims 1 to 5, and further comprising an alkali-soluble resin, a photopolymerization initiator, and a solvent.

7. A pattern comprising a cured product of the photosensitive resin composition of claim 6.

8. The pattern according to claim 7, wherein, The pattern has a refractive index of 1.6 or higher at a wavelength of 550 nm.

9. A display device comprising the pattern of claim 7.

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