Compound, method for preparing same, and crosslinking agent, photosensitive resin composition, cured film, and electronic device, comprising same

Abstract

The present invention relates to a compound having a novel structure, a method for preparing same, and a crosslinking agent, a photosensitive resin composition, a cured film, and an electronic device, comprising same.

Description

Compound and method for producing the same, crosslinking agent including the same, photosensitive resin composition, cured film, and electronic device

[0001] Cross-citation with related application(s)

[0002] This application claims the benefit of priority to Korean Patent Application No. 10-2024-0031401, filed March 5, 2024, the entire contents of which are incorporated herein by reference.

[0003] The present invention relates to a compound having excellent heat resistance and tensile properties, a method for producing the same, a crosslinking agent including the same, a photosensitive resin composition, a cured film, and an electronic device.

[0004] Photosensitive resin is a representative functional polymer material that has been put into practical use in the production of various precision electronic and information industry products, and is currently being used significantly in advanced technology industries, especially in the production of semiconductors and displays.

[0005] In general, photosensitive resins are polymer compounds whose molecular structure undergoes chemical changes in response to light within a short period of time, resulting in changes in physical properties such as solubility in specific solvents, coloring, and curing. Photosensitive resins enable micro-precision processing, significantly reduce energy and raw material usage compared to thermal reaction processes, and allow for rapid and accurate work in small installation spaces. Therefore, they are widely used in various precision electronics and information industries, including advanced printing, semiconductor production, display production, and photocurable surface coating materials.

[0006] Meanwhile, with the recent advancements in electronic devices, including their high integration and micropatterning, there is a growing demand for photosensitive resins that can minimize defect rates and enhance processing efficiency and resolution. Accordingly, methods using polyimide or polybenzoxazole, which are highly resistant to external heat, chemicals, and impact, as photosensitive resins have been introduced.

[0007] However, as the degree of fairness (especially development during the lithography process) is increased, there is a limit to the film quality of the cured product being easily broken, and therefore, improvement of tensile properties is required to ensure reliability against external physical stimuli.

[0008] For this purpose, it is well known to use epoxies containing alkylene oxide groups. However, epoxies containing alkylene oxide groups have the problem that as the proportion in the composition increases, the total content of flexible functional groups in the composition increases, resulting in a lower glass transition temperature (Tg) of the final cured film.

[0009] Accordingly, there is a need for the development of a composition that can improve tensile properties without lowering the glass transition temperature.

[0010] The present invention provides a compound having excellent heat resistance and tensile properties.

[0011] In addition, the present invention provides a method for producing the compound.

[0012] In addition, the present invention provides a crosslinking agent including the above compound.

[0013] In addition, the present invention provides a photosensitive resin composition including the compound.

[0014] In addition, the present invention provides a cured film and an electronic device manufactured using the compound or the photosensitive resin composition.

[0015] In this specification, a compound represented by chemical formula 1 is provided.

[0016] The present specification also provides a method for producing a compound, comprising: a step of reacting a compound represented by Chemical Formula 3 and dicyandiamide to produce a compound represented by Chemical Formula 4; a step of reacting a compound represented by Chemical Formula 4 and formaldehyde to produce a compound represented by Chemical Formula 5; and a step of reacting a compound represented by Chemical Formula 5 and an alcohol.

[0017] Also provided herein is a crosslinking agent comprising the compound.

[0018] The present specification also provides a photosensitive resin composition comprising the compound.

[0019] In addition, the present specification provides a cured film including a cured product of the photosensitive resin composition.

[0020] In addition, the present specification provides an electronic device including the cured film.

[0021] Hereinafter, a compound and a method for producing the compound, a crosslinking agent including the compound, a photosensitive resin composition, a cured film, and an electronic device according to specific embodiments of the invention will be described in more detail.

[0022]

[0023] In this specification, when a part is said to "include" a certain component, this does not mean that it excludes other components, but rather that it may include other components, unless specifically stated otherwise.

[0024] In this specification, examples of substituents are described below, but are not limited thereto.

[0025] In this specification, the term "substitution" means that another functional group is bonded instead of a hydrogen atom in a compound, and the position of substitution is not limited as long as it is a position where a hydrogen atom is substituted, i.e., a position where a substituent can be substituted, and when two or more are substituted, the two or more substituents may be the same or different from each other.

[0026] The term "substituted or unsubstituted" as used herein means a group that is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a carbonyl group; an ester group; an imide group; an amide group; an amino group; a carboxyl group; a sulfonic acid group; a sulfonamide group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkylsulfoxy group; an arylsulfoxy group; a silyl group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an arylphosphine group; or a heterocyclic group containing at least one of N, O, and S atoms, or a substituted or unsubstituted group in which two or more of the above-mentioned substituents are linked. For example, the "substituent linked with two or more substituents" may be a biphenyl group. That is, the biphenyl group can be an aryl group or can be interpreted as a substituent in which two phenyl groups are connected.

[0027] In this specification, , or means a bond that is connected to another substituent, and a direct bond means that there is no separate atom in the part indicated by L.

[0028] In this specification, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

[0029] In this specification, alkyl is a monovalent functional group derived from an alkane, which may be straight-chain or branched, and the number of carbon atoms in the straight-chain alkyl is not particularly limited, but is preferably 1 to 20. In addition, the number of carbon atoms in the branched-chain alkyl is 3 to 20. Specific examples of alkyl include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, 2,6-dimethylheptan-4-yl, etc., but are not limited thereto. The alkyl may be substituted or unsubstituted, and when substituted, examples of the substituent are as described above.

[0030] In the present specification, cycloalkyl is a monovalent functional group derived from cycloalkane, which may be monocyclic or polycyclic, and has, but is not particularly limited to, 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl has 3 to 10 carbon atoms. Specifically, examples thereof include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2,2,1]heptyl, and the like. The cycloalkyl may be substituted or unsubstituted, and when substituted, examples of the substituent are as described above.

[0031] In this specification, alkoxy is a functional group in which the above-mentioned alkyl is bonded to one end of an ether group (-O-), and the description of the above-mentioned alkyl can be applied except that it is a functional group bonded to an ether group (-O-). For example, it can be a straight chain, a branched chain, or a cyclic chain. The carbon number of the alkoxy is not particularly limited, but it is preferably 1 to 20 carbon atoms. Specifically, examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, cycloheptoxy, benzyloxy, p-methylbenzyloxy, and the like. The above alkoxy may be substituted or unsubstituted.

[0032] In the present specification, aryl is a monovalent functional group derived from arene, and is not particularly limited, but preferably has 6 to 20 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. The monocyclic aryl may be, but is not limited to, phenyl, biphenyl, terphenyl, etc. The polycyclic aryl may be, but is not limited to, naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, chrysenyl, fluorenyl, etc. The aryl may be substituted or unsubstituted, and when substituted, examples of the substituent are as described above.

[0033] In the present specification, alkylene is a divalent functional group derived from an alkane, and the description of alkyl described above may be applied to these except that they are divalent functional groups. For example, they may be straight-chain or branched, and may be methylene, ethylene, propylene, isobutylene, sec-butylene, tert-butylene, pentylene, hexylene, etc. The alkylene may be substituted or unsubstituted, and when substituted, examples of the substituent are as described above.

[0034] In the present specification, arylene is a divalent functional group derived from arene, and the description of aryl described above may be applied to these except that they are divalent functional groups. For example, they may be phenylene, biphenylene, terphenylene, naphthalene, fluorenyl, pyrenyl, phenanthrenyl, perylene, tetracenyl, anthracenyl, etc. The arylene may be substituted or unsubstituted, and when substituted, examples of the substituent are as described above.

[0035] In this specification, cycloalkylene is a divalent functional group derived from cycloalkane, and the description of cycloalkyl described above may be applied except that it is a divalent functional group. The cycloalkylene may be substituted or unsubstituted, and when substituted, examples of the substituent are as described above.

[0036] In this specification, “direct bond” means that no atom or atomic group exists at that position, but is connected by a bond line.

[0037]

[0038] According to one embodiment of the invention, a compound represented by the following chemical formula 1 can be provided.

[0039] [Chemical Formula 1]

[0040]

[0041] In the above chemical formula 1,

[0042] R1 to R8 are the same or different from each other, and each independently represents one of alkyl, arylalkyl, or alkoxyarylalkyl,

[0043] L is a functional group represented by the following chemical formula 2,

[0044] [Chemical Formula 2]

[0045]

[0046] In the above chemical formula 2,

[0047] X1, X2, X3 are the same or different and each independently represents a direct bond, -O-, -COO-, -CONR9-, -O(CO)O-, or -NR 10 (CO)NR 11 - is one of them,

[0048] R9 to R above 11 are the same or different from each other, and each independently represents hydrogen, alkyl, cycloalkyl, or aryl,

[0049] A1, A2, B1, and B2 are the same or different from each other, and are each independently one of alkylene, cycloalkylene, or arylene,

[0050] n, m, p, q are equal or different, and are each independently integers of 0 or 1, and at least one of n, m, p, q is 1.

[0051] The inventors of the present invention have confirmed through experiments that the compound represented by the chemical formula 1 can be used as a crosslinking agent because it can react with an electron rich system in heat or acid due to its chemical structure as shown in the chemical formula 1, and that the tensile properties of a cured film containing the compound represented by the chemical formula 1 can be significantly improved because it has a large number of crosslinking sites (eight), and that the glass transition temperature can be suppressed from lowering, thereby completing the invention.

[0052] In the above chemical formula 1, R1 to R8 are the same or different, and can each independently be one of alkyl, arylalkyl, or alkoxyarylalkyl. The arylalkyl refers to a functional group in which a hydrogen atom contained in alkyl is replaced with aryl. In addition, the alkoxyarylalkyl refers to a functional group in which a hydrogen atom contained in alkyl is replaced with alkoxyaryl, and the alkoxyaryl refers to a functional group in which a hydrogen atom contained in aryl is replaced with alkoxy.

[0053] Specifically, in the above chemical formula 1, R1 to R8 are the same as or different from each other, and can each independently be one of alkyl having 1 to 5 carbon atoms, arylalkyl having 7 to 20 carbon atoms, or alkoxyarylalkyl having 8 to 30 carbon atoms.

[0054] Meanwhile, in the above chemical formula 2, X1, X2, and X3 are the same or different from each other, and each independently represents a direct bond, -O-, -COO-, -CONR9-, -O(CO)O-, or -NR 10 (CO)NR 11 - can be one of the above -CONR9-, or -NR 10 (CO)NR 11 -R9 to R listed in 11 are the same or different from each other, and each can independently be one of hydrogen, alkyl, cycloalkyl, or aryl. More specifically, the R9 can be hydrogen, methyl, or ethyl. In addition, the R 10 and R 11 are the same or different from each other, and each can independently be hydrogen or methyl.

[0055] In the above chemical formula 2, X1, X2, and X3 can all be direct bonds.

[0056] In addition, in the above chemical formula 2, at least one of X1, X2, and X3 is -O-, -COO-, -CONR9-, -O(CO)O-, or -NR 10 (CO)NR 11 - may be one of the following. That is, at least one of the above X1, X2, X3 is -O-, -COO-, -CONR9-, -O(CO)O-, or -NR 10 (CO)NR 11- can be. This can significantly improve the tensile properties of a cured film containing a compound represented by chemical formula 1 by securing molecular flexibility in the molecular structure and increasing the packing property between polymer chains, while suppressing a decrease in the glass transition temperature.

[0057] In the above chemical formula 2, specific examples of X1, X2, and X3 are not particularly limited, but for example, they may be one of -O-, -COO-, -CONH-, -CON(CH3)-, -CON(CH2CH3)-, -O(CO)O-, -NH(CO)NH-, or -N(CH3)(CO)N(CH3)-.

[0058] On the other hand, in the above chemical formula 2, at least one of X1, X2, and X3 is -NR 12 -(R 12 If the amine group is hydrogen, alkyl, cycloalkyl, alkoxyalkyl, or aryl, not only does the manufacturing process become more complicated, but reliability (especially heat / moisture resistance) may deteriorate as the number of amine groups increases.

[0059] Meanwhile, in the above chemical formula 2, A1, A2, B1, and B2 are the same or different from each other, and can each independently be one of alkylene, cycloalkylene, or arylene.

[0060] The specific examples of the above A1, A2, B1, and B2 are not particularly limited, but may be, for example, one of methylene, ethylene, normal propylene, 1,3-butanediyl, cyclohexylene, 1,3-phenylene, 5-methyl-1,3-phenylene, 2,5-dimethyl-1,4-phenylene, 1,5-naphthylene, or 1,6-naphthylene. This ensures molecular flexibility while strengthening pi-pi interactions, thereby significantly improving the tensile properties of a cured film containing the compound represented by chemical formula 1, while suppressing a decrease in the glass transition temperature.

[0061] Meanwhile, in the above chemical formula 2, n, m, p, and q are the same or different from each other, and are each independently an integer of 0 or 1, and at least one of n, m, p, and q may be 1. That is, at least one of n, m, p, and q may be 1.

[0062] In the above chemical formula 2, (n+m+p+q) may be 2 to 4, or 3 to 4, or 4. This ensures molecular flexibility while strengthening pi-pi interactions, thereby significantly improving the tensile properties of a cured film containing the compound represented by chemical formula 1, while suppressing a decrease in the glass transition temperature.

[0063] More specifically, the functional group represented by the above chemical formula 2 may be any one selected from the group consisting of the following. However, specific examples of the functional group represented by the above chemical formula 2 are not limited to the group consisting of the following.

[0064]

[0065]

[0066]

[0067] .

[0068] Meanwhile, the compound represented by the above chemical formula 1 may include a compound represented by any one of the following chemical formulas 1-1 to 1-12. However, specific examples of the compound represented by the above chemical formula 1 are not limited to compounds represented by any one of the following chemical formulas 1-1 to 1-12.

[0069] [Chemical Formula 1-1]

[0070]

[0071] [Chemical Formula 1-2]

[0072]

[0073] [Chemical Formula 1-3]

[0074]

[0075] [Chemical Formula 1-4]

[0076]

[0077] [Chemical Formula 1-5]

[0078]

[0079] [Chemical Formula 1-6]

[0080]

[0081] [Chemical Formula 1-7]

[0082]

[0083] [Chemical Formula 1-8]

[0084]

[0085] [Chemical Formula 1-9]

[0086]

[0087] [Chemical Formula 1-10]

[0088]

[0089] [Chemical Formula 1-11]

[0090]

[0091] [Chemical Formula 1-12]

[0092] .

[0093]

[0094] The compound of the above embodiment has a Formaldehyde index according to EPA Method 8315A of 38 ppm or less, or 37 ppm or less, or 32 ppm or less, or 29 ppm or less, or 26 ppm or less, or 25 ppm or less, or 24 ppm or less, or 23 ppm or less, or 21 ppm or less, or 20 ppm or less, or 19 ppm or less, or 18 ppm or less, or 17 ppm or less, or 1 ppm or more, or 1 ppm to 38 ppm, or 1 ppm to 37 ppm, or 1 ppm to 32 ppm, or 1 ppm to 29 ppm, or 1 ppm to 26 ppm, or 1 ppm to 25 ppm, or 1 ppm to 24 ppm, or 1 ppm to 23 ppm, or 1 ppm to 21 ppm, or 1 It may be from ppm to 20 ppm, or from 1 ppm to 19 ppm, or from 1 ppm to 18 ppm, or from 1 ppm to 17 ppm.

[0095] There are no specific limitations on the specific examples of the method for measuring the Formaldehyde index according to the above EPA Method 8315A, and for example, the method may be measured using the EPA (US Environmental Protection Agency) Method 8315A (SW-846).

[0096] Formaldehyde has a highly pungent odor that irritates the nose and eyes, and is a substance that contains harmful components to humans and the natural environment. Recently, it has been suspected of being a carcinogen, and interest in it has been increasing worldwide. Legal regulations are being strengthened, requiring that formaldehyde not be included in the manufacturing process of compounds. The compound of the above embodiment enables the synthesis of an environmentally friendly compound because the formaldehyde index according to EPA Method 8315A is reduced to 38 ppm or less.

[0097]

[0098] Meanwhile, according to another embodiment of the invention, a method for producing a compound may be provided, including a step of reacting a compound represented by the following chemical formula 3 and dicyandiamide to produce a compound represented by the following chemical formula 4; a step of reacting a compound represented by the above chemical formula 4 and formaldehyde to produce a compound represented by the following chemical formula 5; and a step of reacting a compound represented by the above chemical formula 5 and an alcohol.

[0099] [Chemical Formula 3]

[0100]

[0101] [Chemical Formula 4]

[0102]

[0103] [Chemical Formula 5]

[0104]

[0105] In the above chemical formulas 3 to 5,

[0106] L is a functional group represented by the following chemical formula 2,

[0107] [Chemical Formula 2]

[0108]

[0109] In the above chemical formula 2,

[0110] X1, X2, X3 are the same or different and each independently represents a direct bond, -O-, -COO-, -CONR9-, -O(CO)O-, or -NR 10 (CO)NR 11 - is one of them,

[0111] R9 to R above 11 are the same or different from each other, and each independently represents hydrogen, alkyl, cycloalkyl, or aryl,

[0112] A1, A2, B1, and B2 are the same or different from each other, and are each independently one of alkylene, cycloalkylene, or arylene,

[0113] n, m, p, q are equal or different, and are each independently integers of 0 or 1, and at least one of n, m, p, q is 1.

[0114] The content of the above chemical formula 2 includes the content described above with respect to the above embodiment.

[0115] In the step of producing a compound represented by the above chemical formula 4 by reacting the compound represented by the above chemical formula 3 and dicyandiamide, dicyandiamide may be added in a sufficiently excessive amount compared to the compound represented by the above chemical formula 3 so that dicyandiamide can react with both terminal cyano groups of the compound represented by the above chemical formula 3.

[0116] In addition, in the step of reacting the compound represented by the above chemical formula 3 and dicyandiamide to produce the compound represented by the above chemical formula 4, the reaction between the compound represented by the above chemical formula 3 and dicyandiamide may proceed under basic conditions. Examples of the base are not particularly limited, but for example, KOH may be used. In addition, the reaction between the compound represented by the above chemical formula 3 and dicyandiamide may proceed under a solvent. Examples of the solvent are not particularly limited, but for example, 2-Methoxyethanol may be used.

[0117] Meanwhile, in the step of reacting the compound represented by the above chemical formula 4 and formaldehyde to produce the compound represented by the above chemical formula 5, formaldehyde may be added in a sufficiently excessive amount compared to the compound represented by the chemical formula 4 so that formaldehyde can react entirely with the terminal amino group of the compound represented by the above chemical formula 4.

[0118] In addition, in the step of reacting the compound represented by the above chemical formula 4 and formaldehyde to produce the compound represented by the above chemical formula 5, the reaction between the compound represented by the above chemical formula 4 and formaldehyde may proceed under basic conditions. Examples of the above base are not particularly limited, but for example, NaHCO3 may be used.

[0119] Meanwhile, in the step of reacting the compound represented by the above chemical formula 5 and the alcohol, the alcohol may include a compound represented by the following chemical formula 6.

[0120] [Chemical Formula 6]

[0121] R 13 -OH

[0122] In the above chemical formula 6,

[0123] R 13 is one of alkyl, arylalkyl, or alkoxyarylalkyl.

[0124] In the above chemical formula 6, R 13 It can be one of alkyl, arylalkyl, or alkoxyarylalkyl. The arylalkyl refers to a functional group in which a hydrogen atom contained in alkyl is replaced with aryl. In addition, the alkoxyarylalkyl refers to a functional group in which a hydrogen atom contained in alkyl is replaced with alkoxyaryl, and the alkoxyaryl refers to a functional group in which a hydrogen atom contained in aryl is replaced with alkoxy.

[0125] Specifically, in the above chemical formula 6, R 13 It can be one of alkyl having 1 to 5 carbon atoms, arylalkyl having 7 to 20 carbon atoms, or alkoxyarylalkyl having 8 to 30 carbon atoms.

[0126] Additionally, in the step of reacting the compound represented by the above chemical formula 5 and the alcohol, the alcohol may be added in sufficient excess compared to the compound represented by the chemical formula 5 so that the alcohol can react entirely with the terminal hydroxyl group of the compound represented by the chemical formula 5.

[0127] In addition, in the step of reacting the compound represented by the above chemical formula 5 and the alcohol, the reaction between the compound represented by the above chemical formula 5 and the alcohol may proceed under acid conditions. Examples of the acid are not particularly limited, but for example, HCl may be used.

[0128] Additionally, the reaction between the compound represented by the above chemical formula 5 and an alcohol can proceed in a solvent. Examples of the solvent are not particularly limited, but for example, toluene can be used.

[0129] Meanwhile, after the step of reacting the compound represented by the above chemical formula 5 and the alcohol, a neutralization step may be further performed. Since the step of reacting the compound represented by the above chemical formula 5 and the alcohol is performed under acidic conditions, a base may be added in the neutralization step. Examples of the base are not particularly limited, but, for example, NaOH may be used.

[0130] After the compound represented by Chemical Formula 1 of the above embodiment is synthesized through the compound preparation method of the other embodiment, a filtration step or a drying step may be additionally performed as needed. The contents of the filtration step and the drying step can be applied without limitation to various methods, equipment, conditions, etc. that have been widely used in the field of compound synthesis in the past.

[0131]

[0132] Meanwhile, according to another embodiment of the invention, a crosslinking agent comprising the compound of the above embodiment can be provided.

[0133] The content of the compound includes the content described above with respect to the above embodiment. The various functional groups contained in the compound form a crosslinking structure with the functional groups contained in the polyimide during a heat or acid-mediated curing process, and due to this crosslinking structure, a crosslinking structure can be formed with another adjacent polyimide. Accordingly, the photosensitive resin composition containing the crosslinking agent of the above other embodiment can significantly increase tensile strength while maintaining high resistance to various chemicals and heat.

[0134]

[0135] Meanwhile, according to another embodiment of the invention, a photosensitive resin composition comprising the compound of the above embodiment can be provided.

[0136] The content regarding the above compound includes the content described above with respect to the above embodiment.

[0137] The photosensitive resin composition may further include a binder resin. The binder resin is not particularly limited, as long as it can exhibit the physical properties, such as strength and developability, of a film manufactured from the resin composition. However, for example, polyimide or polybenzoxazole may be used.

[0138] In addition, the photosensitive resin composition may further include a photoinitiator. The photoinitiator is not particularly limited as long as it is an initiator that generates radicals by light to trigger crosslinking, but may be, for example, at least one selected from the group consisting of benzophenone-based compounds, acetophenone-based compounds, biimidazole-based compounds, triazine-based compounds, and oxime-based compounds.

[0139] The photosensitive resin composition may further comprise a solvent. As the solvent, any compound known in the technical field to which the present invention pertains that enables the formation of a photosensitive resin composition layer may be used without particular limitation. As a non-limiting example, the solvent may be one or more compounds selected from the group consisting of esters, ethers, ketones, aromatic hydrocarbons, and sulfoxides.

[0140] In addition, the photosensitive resin composition may further include one or two or more additives selected from the group consisting of an antioxidant, a photocrosslinking agent, a curing accelerator, an adhesion accelerator, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersant, and a leveling agent.

[0141]

[0142] Meanwhile, according to another embodiment of the invention, a cured film comprising a cured product of the photosensitive resin composition may be provided. The cured product refers to a material obtained through a curing process of the photosensitive resin composition of the other embodiment. The information regarding the photosensitive resin composition includes the information described above with respect to the other embodiment. The cured film may include both an organic insulating film and a photosensitive pattern.

[0143] The above cured film exhibits excellent heat resistance and tensile properties, and can be applied to insulating films of semiconductor devices, interlayer insulating films for redistribution layers, etc. In addition, the above cured film can be applied to photoresists, etching resists, solder top resists, etc.

[0144]

[0145] Meanwhile, according to another embodiment of the invention, an electronic device including a cured film of the above embodiment can be provided. The content regarding the cured film includes the content described above with respect to the other embodiment.

[0146] An electronic device including an organic insulating film or a photosensitive pattern formed from a photosensitive resin composition containing the compound of the above embodiment can have excellent performances such as high resolution and high sensitivity, and can exhibit excellent film properties and high mechanical properties, as well as excellent heat resistance properties, for example, properties in which the adhesion of the organic insulating film or the photosensitive pattern is not deteriorated and can be maintained firmly even when used for a long period of time or exposed to high temperature conditions for a long period of time.

[0147] Examples of the above electronic components include semiconductor devices.

[0148] According to the present invention, a compound having excellent heat resistance and tensile properties, a crosslinking agent including the compound, a photosensitive resin composition, a cured film, and an electronic device can be provided.

[0149] The invention is described in more detail in the following examples. However, the following examples are merely illustrative of the present invention, and the scope of the present invention is not limited by the following examples.

[0150]

[0151] <Manufacturing Example 1>: Synthesis of compounds 1 to 12

[0152] (1) Preparation of compound 1

[0153] Compound 1 was synthesized through a reaction as shown in [Reaction Scheme 1] below.

[0154] [Reaction Formula 1]

[0155]

[0156] A 500 ml round bottom flask was charged with 8 g (0.1 mol) of Succinonitrile (SM1, CAS: 110-61-2), 17.6 g (1 mol, 2.1 eq) of Dicyandiamide (CAS: 461-58-5), 0.56 g (0.01 mol, 0.1 eq) of KOH, and 80 ml of 2-Methoxyethanol, and refluxed for 12 hours. After completion of the reaction, the mixture was stirred at room temperature for an additional hour, and then filtered to obtain compounds P1-2.

[0157] In a 500 ml round bottom flask, add the P1-2 compound obtained above, 0.84 g (0.01 mol, 0.1 eq) of NaHCO3, and 80 ml (1 mol, 10 eq) of 35% formaldehyde aqueous solution, and then 80 The mixture was stirred at ℃ for 12 hours. After the reaction was completed, 40 ml of acetonitrile was slowly added. After the reaction was completed, the mixture was stirred for an additional hour at room temperature and filtered to obtain compound P1-1.

[0158] Add the P1-1 compound obtained above and 80 ml of methanol to a 250 ml round bottom flask and add 5 After cooling to ℃, 0.12 ml (0.01 mol, 0.1 eq) of 37% hydrochloric acid was added. After warming to room temperature, the mixture was stirred until completely dissolved. After completion of the reaction, 40 ml of 5% NaOH solution was slowly added. After stirring for 1 hour, a solid was formed. After filtration, 80 After drying using a ℃ vacuum oven, 12 g of compound 1 was obtained (yield 12%).

[0159] 1H NMR (500MHz, Acetone-D6, ppm): 5.2 (s, 16H), 3.3-3.5 (broad, 24H), 2.5 (s, 4H)

[0160] HRMS [M+H] + : 601.3381

[0161]

[0162] (2) Preparation of compound 2

[0163] Compound 2 was synthesized through a reaction as shown in [Reaction Scheme 2] below.

[0164] [Reaction Formula 2]

[0165]

[0166] Specifically, as in the above [Reaction Scheme 2], 15 g of compound 2 was obtained in the same manner as in the preparation example of compound 1, except that 16 g (0.1 mol) of SM2 compound (CAS: 90872-59-6) was used instead of 8 g (0.1 mol) of Succinonitrile (SM1, CAS: 110-61-2). (Yield: 21%)

[0167] 1 H NMR (500MHz, Acetone-D6, ppm): 5.1 (s, 16H), 3.2-3.4 (broad, 24H), 2.52 (d, 4H), 1.79 (multiplet, 2H), 1.6 (m, 4H), 1.4 (m, 4H)

[0168] HRMS [M+H] + : 683.4162

[0169]

[0170] (3) Preparation of compound 3

[0171] Compound 3 was synthesized through a reaction as shown in [Reaction Scheme 3] below.

[0172] [Reaction Formula 3]

[0173]

[0174] Specifically, as in the above [Reaction Scheme 3], 15 g of P3-1 compound was synthesized in the same manner as in the preparation example of compound 1, except that 13 g (0.1 mol) of SM3 compound (CAS: 626-17-5) was used instead of 8 g (0.1 mol) of Succinonitrile (SM1, CAS: 110-61-2).

[0175] Add the P3-1 compound obtained above and 100 ml of ethanol to a 250 ml round bottom flask and add 5 After cooling to ℃, 0.24 ml (0.02 mol, 0.2 eq) of 37% hydrochloric acid was added. After warming to room temperature, the mixture was stirred until completely dissolved. After completion of the reaction, 50 ml of 5% NaOH solution was slowly added. After stirring for 1 hour, a solid was formed. After filtration, 80 After drying using a ℃ vacuum oven, 18.2 g of compound 3 was obtained (yield 24%).

[0176] 1 H NMR (500MHz, Acetone-D6, ppm): 8.45 (d, 2H), 7.87 (s, 1H), 7.65 (t, 1H), 5.4(s, 16H), 3.5(q, 16H), 1.1(t, 24H)

[0177] HRMS [M+H] + : 761.4626

[0178]

[0179] (4) Preparation of compound 4

[0180] Compound 4 was synthesized through a reaction as shown in [Reaction Scheme 4] below.

[0181] [Reaction Formula 4]

[0182]

[0183] Specifically, as in the above [Reaction Scheme 4], P4-1 compound was synthesized in the same manner as in the preparation example of compound 1, except that 18 g (0.1 mol) of SM4 compound (CAS: 46289-40-1) was used instead of 8 g (0.1 mol) of Succinonitrile (SM1, CAS: 110-61-2).

[0184] Add the P4-1 compound obtained above and 100 ml isopropanol to a 500 ml round bottom flask and add 5 After cooling to ℃, 1.2 ml (0.1 mol, 1 eq) of 37% hydrochloric acid was added. After warming to room temperature, the mixture was stirred until completely dissolved. After completion of the reaction, 50 ml of 5% NaOH solution was slowly added. After stirring for 1 hour, a solid was formed. After filtration, 80 After drying using a ℃ vacuum oven, 23 g of compound 4 was obtained (yield 25%).

[0185] Add 100 ml of isopropanol to the P4-1 compound in a 500 ml round bottom flask and add 5 o After cooling to C, 1.2 ml (0.1 mol, 1 eq) of 37% hydrochloric acid was added. After raising to room temperature, it was stirred until completely dissolved. After the reaction was completed, 50 ml of 5% NaOH solution was slowly added. After stirring for 1 hour, a solid was formed. After filtration, 80 o After drying using a C vacuum oven, 23 g (3 steps, yield 25%) of compound 4 was obtained.

[0186] 1 H NMR (500MHz, Acetone-D6, ppm): 8.3-8.4 (m, 2H), 8.1-8.2 (m, 4H), 5.5(s, 16H), 3.65(m, 8H), 1.2(d, 48H)

[0187] HRMS [M+H] + : 923.6035

[0188]

[0189] (5) Preparation of compound 5

[0190] Compound 5 was synthesized through a reaction as shown in [Reaction Scheme 5] below.

[0191] [Reaction Formula 5]

[0192]

[0193] Specifically, as in the above [Reaction Scheme 5], P5-1 compound was synthesized in the same manner as in the preparation example of compound 1, except that 12.5 g (0.1 mol) of SM5 compound (CAS: 1656-48-0) was used instead of 8 g (0.1 mol) of Succinonitrile (SM1, CAS: 110-61-2).

[0194] A 500-ml round-bottom flask was charged with the above-mentioned P5-1 compound, 138 g (1 mol, 10 eq) of 4-Methoxybenzylalcohol, 1.92 g (0.01 mol, 0.1 eq) of p-Toluenesulfonic acid, and 280 ml of toluene, followed by reflux. After completion of the reaction, 140 ml of 5% NaOH solution was slowly added and neutralized. The toluene layer was extracted, and the solvent was removed to obtain an orange solid. Recrystallization with ethanol yielded 22 g of compound 5 (yield: 15%).

[0195] 1 H NMR (500MHz, Acetone-D6, ppm): 7.01 (d, 16H), 6.88 (d, 16H), 5.6 (s, 16H), 4.9 (s, 16H), 3.9 (s, 24H), 3.4 (t, 4H), 2.5 (t, 4H)

[0196] HRMS [M+H] +: 1493.6982

[0197]

[0198] (6) Preparation of compound 6

[0199] Compound 6 was synthesized through a reaction as shown in [Reaction Scheme 6] below.

[0200] [Reaction Formula 6]

[0201]

[0202] Specifically, as in the above [Reaction Scheme 6], 24 g of compound 6 was obtained in the same manner as in the preparation example of compound 1, except that 28 g (0.1 mol) of SM6 compound (CAS: 7476-06-4) was used instead of 8 g (0.1 mol) of Succinonitrile (SM1, CAS: 110-61-2). (Yield: 30%)

[0203] 1 H NMR (500MHz, Acetone-D6, ppm): 8.1 (d, 4H), 7.1 (d, 4H), 5.5 (s, 16H), 4.2 (t, 4H), 3.4 (s, 24H), 2.2 (m, 2H)

[0204] HRMS [M+H] + : 799.4062

[0205]

[0206] (7) Preparation of compound 7

[0207] Compound 7 was synthesized through a reaction as shown in [Reaction Scheme 7] below.

[0208] [Reaction Formula 7]

[0209]

[0210] Specifically, as in the above [Reaction Scheme 7], P7-1 compound was synthesized in the same manner as in the preparation example of compound 1, except that 24 g (0.1 mol) of SM7 compound (CAS: 90870-40-9) was used instead of 8 g (0.1 mol) of Succinonitrile (SM1, CAS: 110-61-2).

[0211] A 500-ml round-bottom flask was charged with the above-mentioned P7-1 compound, 108 g (1 mol, 10 eq) of benzyl alcohol, 1.92 g (0.01 mol, 0.1 eq) of p-toluenesulfonic acid, and 220 ml of toluene, followed by reflux. After completion of the reaction, 110 ml of 5% NaOH solution was slowly added and neutralized. The toluene layer was extracted, and the solvent was removed to obtain a yellow solid. Recrystallization with ethanol yielded 36 g of compound 7 (yield: 26%).

[0212] 1 H NMR (500MHz, Acetone-D6, ppm): 7.2-7.35 (m, 40H), 5.3 (s, 16H), 4.7 (s, 16H), 4.2 (t, 4H), 3.7 (t, 4H), 3.4 (s, 4H)

[0213] HRMS [M+H] + : 1369.6258

[0214]

[0215] (8) Preparation of compound 8

[0216] Compound 8 was synthesized through a reaction as shown in [Reaction Scheme 8] below.

[0217] [Reaction Formula 8]

[0218]

[0219] As shown in the above [Reaction Scheme 8], 30 g (0.25 mol) of 3-cyanophenol (SM8-1, CAS: 873-62-1), 20 g (0.12 mol, 0.5 eq) of carbonyl diimidazole (CDI, CAS: 530-62-1), 1.5 g (0.012 mol, 0.05 eq) of N,N-Dimethylaminopyridine (DMAP), and 120 ml of Tetrahydrofuran (THF) were added to a 250 ml round bottom flask and refluxed for 12 hours. After completion of the reaction, half of the solvent was removed, 120 ml of ethanol was slowly added, and the formed solid was filtered to obtain 28.2 g of SM8 compound.

[0220] Thereafter, as in the above [Reaction Scheme 8], P8-1 compound was synthesized in the same manner as in the preparation example of compound 1, except that 26 g (0.1 mol) of SM8 compound was used instead of (0.1 mol) of Succinonitrile (SM1, CAS:110-61-2).

[0221] In a 250-ml round-bottom flask, the P8-1 compound obtained above and 200 ml of n-butanol were placed, and then 1.2 ml (0.1 mol, 1 eq) of 37% hydrochloric acid was added. After warming to room temperature, the mixture was stirred until completely dissolved. After completion of the reaction, 50 ml of 5% NaOH solution was slowly added. After stirring for 1 hour, a solid was formed. After filtration, 80 After drying using a ℃ vacuum oven, 12.3 g of compound 8 was obtained (yield 11%).

[0222] 1H NMR (500MHz, Acetone-D6, ppm): 8.1 (d, 2H), 7.4-7.5 (m, 6H), 5.2 (s, 16H) 3.4 (t, 16H), 1.4-1.5 (m, 32H), 1.05 (t, 24H)

[0223] HRMS [M+H] + : 1121.7288

[0224]

[0225] (9) Preparation of compound 9

[0226] Compound 9 was synthesized through a reaction as shown in [Reaction Scheme 9] below.

[0227] [Reaction Formula 9]

[0228]

[0229] Specifically, as in the above [Reaction Scheme 9], 13.7 g of compound 9 was obtained in the same manner as in the preparation example of compound 1, except that 16.6 g (0.1 mol) of SM9 compound (CAS: 7253-99-8) was used instead of 8 g (0.1 mol) of Succinonitrile (SM1, CAS: 110-61-2). (Yield: 20%)

[0230] 1 H NMR (500MHz, Acetone-D6, ppm): 6.5 (brd, 2H), 5.3 (s, 16H), 3.7 (brd, 4H), 3.3 (s, 24H), 2.6 (t, 4H)

[0231] HRMS [M+H] + : 687.3851

[0232]

[0233] (10) Preparation of compound 10

[0234] Compound 10 was synthesized through a reaction as shown in [Reaction Scheme 10] below.

[0235] [Reaction Formula 10]

[0236]

[0237] Specifically, 15 g of P10-1 compound was synthesized in the same manner as in the preparation example of compound 1, except that 26.2 g (0.1 mol) of SM10 (CAS: 1090685-75-8) compound was used instead of 8 g (0.1 mol) of Succinonitrile (SM1, CAS: 110-61-2) as in the above [Reaction Scheme 10].

[0238] In a 5000 ml round bottom flask, the P10-1 compound obtained above and 200 ml of n-propanol were placed, and then 1.2 ml (0.1 mol, 1 eq) of 37% hydrochloric acid was added. After warming to room temperature, the mixture was stirred until completely dissolved. After completion of the reaction, 50 ml of 5% NaOH solution was slowly added. After adding an additional 50 ml of water and stirring for 1 hour, a solid was formed. After filtration, 80 After drying using a ℃ vacuum oven, 18 g of compound 10 was obtained (yield 18%).

[0239] 1 H NMR (500MHz, Acetone-D6, ppm): 8.5-8.65 (m, 2H), 8.3 (d, 1H), 7.9-8.1 (m, 2H), 7.5-7.6 (m, 3H), 5.1-5.3 (m, 18H), 3.3-3.45 (m, 16H), 1.4-1.5 (m, 16H), 0.95-1.05 (t, 24H)

[0240] HRMS [M+H] + : 1007.6252

[0241]

[0242] (11) Preparation of compound 11

[0243] Compound 11 was synthesized through a reaction as shown in [Reaction Scheme 11] below.

[0244] [Reaction Formula 11]

[0245]

[0246] As shown in the above [Reaction Scheme 11], 40 g (0.25 mol) of 4-Cyanophenylacetic acid (SM11-1, CAS: 5462-71-5), 36 g (0.25 mol, 1 eq) of 4-(Ethylamino)benzonitrile (CAS: 4714-63-0), 1.5 g (0.012 mol, 0.05 eq) of N,N-Dimethylaminopyridine (DMAP) and 160 ml of chloroform (CHCl3) were added to a 250 ml round bottom flask, and then 52.8 g (0.28 mol, 1.1 eq) of EDC.HCl.2H2O was slowly added. The reaction was terminated after stirring at room temperature for 12 hours. Work-up was performed using a boric NH4Cl solution. After removing all CHCl3, 120 ml of ethanol was added and stirred. The solid formed was filtered to obtain 54.2 g of SM11 compound.

[0247] Thereafter, as in the above [Reaction Scheme 11], P11-1 compound was synthesized in the same manner as in the preparation example of compound 1, except that 28.9 g (0.1 mol) of SM11 compound was used instead of (0.1 mol) of Succinonitrile (SM1, CAS:110-61-2).

[0248] In a 250-ml round-bottom flask, the P11-1 compound obtained above and 100 ml of ethanol were placed, and then 0.24 ml (0.02 mol, 0.2 eq) of 37% hydrochloric acid was added. After warming to room temperature, the mixture was stirred until completely dissolved. After completion of the reaction, 50 ml of 5% NaOH solution was slowly added and neutralized. After stirring for 1 hour, a solid was formed. After filtration, 80 After drying using a ℃ vacuum oven, 24 g of compound 11 was obtained (yield 26%).

[0249] 1 H NMR (500MHz, Acetone-D6, ppm): 8.6 (d, 2H), 8.17 (d, 2H), 7.66 (d, 2H), 7.4 (d, 2H), 5.2-5.4 (m, 16H), 4.4 (q, 2H), 4.05 (s, 2H), 3.4-3.5 (m, 16H), 1.3 (t, 3H), 0.95-1.1 (m, 24H)

[0250] HRMS [M+H] + : 922.5466

[0251]

[0252] (12) Preparation of compound 12

[0253] Compound 12 was synthesized through a reaction as shown in [Reaction Scheme 12] below.

[0254] [Reaction Formula 12]

[0255]

[0256] Specifically, as in the above [Reaction Scheme 12], 14.8 g of compound 12 was obtained in the same manner as in the preparation example of compound 1, except that 15.6 g of SM12 (CAS: 39095-25-5) was used instead of 8 g (0.1 mol) of Succinonitrile (SM1, CAS: 110-61-2). (Yield: 22%)

[0257] 1 H NMR (500MHz, Acetone-D6, ppm): 7.9 (s, 2H), 5.2 (s, 16H), 3.3 (s, 24H), 2.5 (s, 6H)

[0258] HRMS [M+H] + : 677.3685

[0259]

[0260] <Manufacturing Example 2>: Synthesis of compounds C1 to C2

[0261] (1) Preparation of compound C1

[0262] Compound C1 was synthesized through a reaction as shown in [Reaction Scheme C1] below.

[0263] [Reaction Formula C1]

[0264]

[0265] Specifically, as in the above [Reaction Scheme C1], 18 g of compound C1 was obtained in the same manner as in the preparation example of compound 1, except that 18.7 g (0.1 mol) of 2,4-Diamino-6-phenyl-1,3,5-triazine (PC2-2, CAS:91-76-9) was used instead of 8 g (0.1 mol) of Succinonitrile (SM1, CAS:110-61-2). (Yield: 22%)

[0266] 1 H NMR (500MHz, Acetone-D6, ppm): 8.2 (d, 2H), 7.5-7.6 (m, 3H), 5.3 (s, 16H), 3.5 (s, 24H)

[0267] HRMS [M+H] + : 364.1937

[0268]

[0269] (2) Preparation of compound C2

[0270] Compound C2 was synthesized through a reaction as shown in [Reaction Scheme C2] below.

[0271] [Reaction Formula C2]

[0272]

[0273] Specifically, as in the above [Reaction Scheme C2], 12.3 g (0.1 mol) Melamine (SM13, CAS: 108-78-1), 0.84 g (0.01 mol, 0.1 eq) of NaHCO3, and 40 ml (1 mol, 5 eq) of 35% formaldehyde aqueous solution were added to a 250 ml round bottom flask, and then 80 The mixture was stirred at ℃ for 12 hours. After the reaction was completed, water was removed through distillation under reduced pressure, and the remaining solid (C2-1) was used in the next reaction.

[0274] Add 80 ml of Methanol to the C2-1 compound obtained above and 5 After cooling to ℃, 0.24 ml (0.02 mol, 0.2 eq) of 37% hydrochloric acid was added. After warming to room temperature, the mixture was stirred until completely dissolved. After completion of the reaction, 40 ml of 5% NaOH solution was slowly added. After stirring for 1 hour, a solid was formed. The solid obtained after the filtration process was recrystallized twice more with methanol / water (50 ml / 50 ml) to obtain 5.5 g of compound C2 (yield 8.3%).

[0275] 1 H NMR (500MHz, Acetone-D6, ppm): 6.05(s, 1H, NH), 5.1-5.2(broad,18H), 4.9(s, 2H), 3.3-3.5(broad, 27H), 2.5(s, 4H)

[0276] HRMS [M+H] + : 661.3664

[0277]

[0278] <Manufacturing Example 3>: Synthesis of polyimide resin

[0279] In a round bottom flask, 14.4 g (0.31 mol) of 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane (Bis-AP-AF) was added and dissolved in 500 g of propylene glycol monomethyl ether acetate (PGMEA) at 60°C. 91.1 g (0.29 mol) of 4,4'-oxydiphthalic anhydride (ODPA) was added and stirred for 2 hours. 7.2 g (0.03 mol) of phthalic anhydride was added as a terminal sealant and stirred for an additional 2 hours. The temperature was then raised to 170°C and stirred for 6 hours. The mixture was then cooled to room temperature. The weight average molecular weight (Mw) of the polymerized resin A measured by gel permeation chromatography (GPC) was 15,000 g / mol, and the degree of imidization (DOI) of the resin A measured by infrared spectroscopy (IR) was 93%. The weight average molecular weight of the polymerized resin A was measured by gel permeation chromatography in a solvent of tetrahydrofuran (THF).

[0280]

[0281] <Manufacturing Example 4>: Manufacturing of photosensitive resin composition

[0282] A photosensitive resin composition was prepared by mixing the compositions described in Tables 1 and 2 below and stirring for 24 hours. The values ​​in Tables 1 and 2 below indicate the weight % of each component based on 100 wt % (solid content) of polyimide resin.

[0283] Composition type Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Resin production example 3 Polyimide 100 wt% 100 wt% 100 wt% 100 wt% 100 wt% 100 wt% 100 wt% 100 wt% Photoactive compound (PAC) MIPHOTOPAC 425 15.50 wt% 15.50 wt% 15.50 wt% 15.50 wt% 15.50 wt% 15.50 wt% 15.50 wt% 15.50 wt% Epoxy curing agent PETG 6 wt% 6 wt% 6 wt% 6 wt% 6 wt% 6 wt% 6 wt% Crosslinking agent Compound 19 wt%------Compound 2-9 wt%-----Compound 3--9 wt%----Compound 4---9 wt%---Compound 5----9 wt%--Compound 6-----9 Weight % Compound 7------9 Weight % Solvent PGMEA 49.9 Weight % 49.9 Weight % 49.9 Weight % 49.9 Weight % 49.9 Weight % 49.9 Weight % 49.9 Weight % 49.9 Weight %

[0284] Composition TypeExample 8Example 9Example 10Example 11Example 12Comparative Example 1Comparative Example 2Resin Preparation Example 3 Polyimide 100 wt% 100 wt% 100 wt% 100 wt% 100 wt% 100 wt% 100 wt% 100 wt% Photoactive Compound (PAC) MIPHOTOPAC 425 15.50 wt% 15.50 wt% 15.50 wt% 15.50 wt% 15.50 wt% 15.50 wt% 15.50 wt% 15.50 wt% Epoxy Curing Agent PETG 6 wt% 6 wt% 6 wt% 6 wt% 6 wt% 6 wt% 6 wt% Crosslinking Agent Compound 8 9 wt%------Compound 9-9 wt%-----Compound 10--9 wt%----Compound 11---9 wt%---Compound 12----9 Weight %--Compound C1-----9 Weight %-Compound C2------9 Weight %Solvent PGMEA49.9 Weight %49.9 Weight %49.9 Weight %49.9 Weight %49.9 Weight %49.9 Weight %49.9 Weight %

[0285] In Table 1 and Table 2 above,

[0286] MIPHOTO PAC425 refers to NAC5 ester with 2,3,4,4'-tetrahydroxy benzophenone of Miwon commercial co., Ltd.

[0287] PETG stands for Pentaerythritol tetraglycidyl ether.

[0288]

[0289] <Experimental Example>

[0290] The properties of the compounds or cured films obtained in the above examples and comparative examples were measured by the following methods, and the results are shown in Table 3.

[0291]

[0292] 1. Formaldehyde index

[0293] For the compounds obtained in the above examples and comparative examples, the formaldehyde index was measured according to EPA (US Environmental Protection Agency) Method 8315A (SW-846).

[0294]

[0295] 2. Young's modulus, tensile strength and elongation

[0296] The photosensitive resin composition of Manufacturing Example 4 was spin-coated on a 6-inch wafer to form a film, and the solvent was evaporated at 120°C for 2 minutes and initially cured. The film was finally cured at 180°C for 2 hours in a nitrogen atmosphere oven (Koyo INH oven), and the film thickness after final curing was 10 μm. To remove the cured film from the wafer, it was immersed in 2.5% HF diluted in DI-water (deionized water) for 30 minutes, and when the film floated, it was taken out and washed three times with distilled water (DI-water). The obtained cured film was dried in a convection oven at 40°C for 1 hour, and then cut into a size of 10 cm × 1 cm to prepare a sample for measuring physical properties.

[0297] After loading the above-mentioned fabricated sample into a UTM (Universal Testing Machine, Zwick) at 25 ℃, Young's modulus, tensile strength, and elongation were measured. At this time, the sample measurement length was set to 1 cm x 5 cm, the pulling speed was set to 10.0 mm / min, and the load cell was 0.5 kN.

[0298]

[0299] 3. Glass transition temperature (Tg) and coefficient of thermal expansion (CTE)

[0300] The photosensitive resin composition of Manufacturing Example 4 was spin-coated on a 6-inch wafer to form a film, and the solvent was evaporated at 120°C for 2 minutes and initially cured. The film was finally cured at 180°C for 2 hours in a nitrogen atmosphere oven (Koyo INH oven), and the film thickness after final curing was 10 μm. To remove the cured film from the wafer, it was immersed in 2.5% HF diluted in DI-water (deionized water) for 30 minutes, and when the film floated, it was taken out and washed three times with distilled water (DI-water). The obtained cured film was dried in a convection oven at 40°C for 1 hour, and then cut into a size of 10 cm × 1 cm to prepare a sample for measuring physical properties.

[0301] The sample manufactured above was heated at a rate of 10°C / min under a nitrogen atmosphere at a temperature of 25°C using TA Q400 equipment, and the glass transition temperature and thermal expansion coefficient were measured.

[0302]

[0303] Experimental example results Formaldehyde index (ppm) Young's modulus (Mpa) Tensile strength (MPa) Elongation (%) CTE (ppm / o C)Tg( oC) Example 1 25 3 4 8 9 1 2 6 3 1 4 1 2 9 2 Example 2 26 3 5 0 1 1 3 0 2 9 3 5 3 0 5 Example 3 20 3 5 20 1 1 5 1 6 1 9 3 5 0 Example 4 18 3 5 1 5 1 1 7 1 7 20 3 5 5 Example 5 21 3 4 8 0 1 2 4 2 6 3 9 2 9 5 Example 6 23 3 4 9 9 1 2 7 2 7 3 0 3 1 0 Example 7 3 2 3 5 0 8 1 3 1 3 5 4 1 2 6 8 Example 82935121211921340Example 93734951243242299Example 102435001192229320Example 111935051182133315Example 121735171252031325Comparative Example 14035101201043265Comparative Example 211035011191560270

[0304] As shown in Table 1 above, it was confirmed that the compound of the example had a lower formaldehyde index than the comparative example. In addition, it was confirmed that the cured film applying the compound of the example had superior mechanical and thermal properties compared to the comparative example.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, R1 to R8 are the same or different from each other, and each independently represents one of alkyl, arylalkyl, or alkoxyarylalkyl, L is a functional group represented by the following chemical formula 2, [Chemical Formula 2] In the above chemical formula 2, X1, X2, X3 are the same or different and each independently represents a direct bond, -O-, -COO-, -CONR9-, -O(CO)O-, or -NR 10 (CO)NR 11 - is one of them, R9 to R above 11 are the same or different from each other, and each independently represents hydrogen, alkyl, cycloalkyl, or aryl, A1, A2, B1, and B2 are the same or different from each other, and are each independently one of alkylene, cycloalkylene, or arylene, n, m, p, q are equal or different, and are each independently integers of 0 or 1, and at least one of n, m, p, q is 1.

2. In paragraph 1, A compound wherein the above A1, A2, B1, and B2 are the same or different from each other, and each independently is one of methylene, ethylene, normal propylene, 1,3-butanediyl, cyclohexylene, 1,3-phenylene, 5-methyl-1,3-phenylene, 2,5-dimethyl-1,4-phenylene, 1,5-naphthylene, or 1,6-naphthylene.

3. In paragraph 1, The functional group represented by the above chemical formula 2 is any one selected from the group consisting of: .

4. In paragraph 1, In the above chemical formula 2, at least one of X1, X2, and X3 is -O-, -COO-, -CONR9-, -O(CO)O-, or -NR 10 (CO)NR 11 - one of the compounds.

5. In paragraph 1, A compound wherein R9 is one of hydrogen, methyl, or ethyl.

6. In paragraph 1, The above R 10 and R 11 are the same or different from each other, and each independently represents hydrogen or methyl.

7. In paragraph 1, A compound in which, in the above chemical formula 2, (n+m+p+q) is 2 to 4.

8. In paragraph 1, A compound in which in the above chemical formula 1, R1 to R8 are the same or different from each other, and each independently represents one of alkyl having 1 to 5 carbon atoms, arylalkyl having 7 to 20 carbon atoms, or alkoxyarylalkyl having 8 to 30 carbon atoms.

9. In paragraph 1, A compound in which in the above chemical formula 1, R1 to R8 are the same or different from each other, and are each independently one of methyl, ethyl, normal propyl, isopropyl, normal butyl, benzyl, or 4-methoxybenzyl.

10. In paragraph 1, A compound in which in the above chemical formula 1, R1 to R8 are the same.

11. In paragraph 1, The compound represented by the above chemical formula 1 is a compound including a compound represented by any one of the following chemical formulas 1-1 to 1-12: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] [Chemical Formula 1-10] [Chemical Formula 1-11] [Chemical Formula 1-12] .

12. In paragraph 1, A compound having a Formaldehyde Index of 38 ppm or less according to EPA Method 8315A.

13. A step of reacting a compound represented by the following chemical formula 3 and dicyandiamide to produce a compound represented by the following chemical formula 4; A step of reacting a compound represented by the above chemical formula 4 and formaldehyde to produce a compound represented by the following chemical formula 5; and A method for producing a compound, comprising a step of reacting a compound represented by the above chemical formula 5 and an alcohol: [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] In the above chemical formulas 3 to 5, L is a functional group represented by the following chemical formula 2, [Chemical Formula 2] In the above chemical formula 2, X1, X2, X3 are the same or different and each independently represents a direct bond, -O-, -COO-, -CONR9-, -O(CO)O-, or -NR 10 (CO)NR 11 - is one of them, R9 to R above 11 are the same or different from each other, and each independently represents hydrogen, alkyl, cycloalkyl, or aryl, A1, A2, B1, and B2 are the same or different from each other, and are each independently one of alkylene, cycloalkylene, or arylene, n, m, p, q are equal or different, and are each independently integers of 0 or 1, and at least one of n, m, p, q is 1.

14. In paragraph 13, The above alcohol is a compound including a compound represented by the following chemical formula 6: [Chemical Formula 6] R 13 -OH In the above chemical formula 6, R 13 is one of alkyl, arylalkyl, or alkoxyarylalkyl.

15. A crosslinking agent comprising the compound of paragraph 1.

16. A photosensitive resin composition comprising the compound of paragraph 1.

17. A cured film comprising a cured product of the photosensitive resin composition of Article 16.

18. An electronic device comprising the cured film of Article 17.