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

Abstract

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

Description

Technical Field

[0001] Cross-references in related fields

[0002] This application claims the benefit of priority based on Korean Patent Application No. 10-2024-0031401, filed on March 5, 2024, and all disclosures in the documents of the Korean Patent Application are incorporated herein by reference.

[0003] This disclosure relates to compounds with excellent heat resistance and tensile properties, methods for their preparation, crosslinking agents comprising the compounds, photosensitive resin compositions, cured layers, and electronic devices. Background Technology

[0004] Photosensitive resin is a representative functional polymer material that has been commercialized in the production of various precision electronic and information industrial products, and is currently being used extensively in advanced technology industries, especially in the production of semiconductors and displays.

[0005] Generally, photosensitive resins refer to polymer compounds that undergo chemical changes in their molecular structure for a short period of time upon light irradiation, resulting in changes in properties such as solubility in specific solvents, coloring, and curing. The use of photosensitive resins enables fine precision machining, offers significant energy and material savings compared to thermal reaction processes, and allows for rapid and accurate operation in small installation spaces. This makes photosensitive resins widely used in various precision electronics and information industries, such as advanced printing, semiconductor manufacturing, display production, and photocurable surface coating materials.

[0006] Meanwhile, as electronic devices have become increasingly integrated and miniaturized, there is a need for photosensitive resins that can minimize defect rates and improve processing efficiency and resolution. Therefore, polyimide or polystyrene resins with strong resistance to external heat, chemicals, and impacts have been introduced. Methods using azoles as photosensitive resins.

[0007] However, the higher the processability (especially the developability in photolithography), the more prone the cured product film quality is to cracking, indicating a need to improve tensile properties to ensure reliability against external physical stimuli.

[0008] For this purpose, it is known to use epoxy resins containing oxidized alkenyl groups. However, the higher the proportion of epoxy resin containing oxidized alkenyl groups in the composition, the higher the total content of flexible functional groups in the composition, which leads to a decrease in the glass transition temperature (Tg) of the final cured layer.

[0009] Therefore, there is a need to develop compositions that can improve tensile properties without lowering the glass transition temperature. Summary of the Invention

[0010] Technical issues

[0011] This disclosure aims to provide compounds with excellent heat resistance and tensile properties.

[0012] Furthermore, this disclosure aims to provide a method for preparing the compound.

[0013] Furthermore, this disclosure is intended to provide a crosslinking agent comprising the said compound.

[0014] Furthermore, this disclosure aims to provide a photosensitive resin composition comprising the said compound.

[0015] Furthermore, this disclosure is intended to provide cured layers and electronic devices manufactured using the said compound or photosensitive resin composition.

[0016] Technical solution

[0017] In this specification, compounds represented by chemical formula 1 are provided.

[0018] This specification also provides a method for preparing the compound, comprising the steps of: reacting the compound represented by chemical formula 3 with dicyandiamide to produce the compound represented by chemical formula 4; reacting the compound represented by chemical formula 4 with formaldehyde to produce the compound represented by chemical formula 5; and reacting the compound represented by chemical formula 5 with an alcohol.

[0019] In addition, crosslinking agents containing the said compounds are provided in this specification.

[0020] In addition, this specification provides photosensitive resin compositions comprising the said compounds.

[0021] In addition, this specification provides a cured layer of a cured product comprising the photosensitive resin composition.

[0022] In addition, this specification provides an electronic device that includes the cured layer.

[0023] The compounds, their preparation methods, crosslinking agents comprising them, photosensitive resin compositions, cured layers, and electronic devices according to specific embodiments of the present invention will be described in more detail below.

[0024] In this specification, unless otherwise expressly stated, when a part is described as "containing" a component, it means that it may also contain other components.

[0025] Examples of substituents are described below in this specification, but are not limited thereto.

[0026] In this specification, the term "substitution" means that a functional group other than a hydrogen atom is bonded to a compound, and there are no restrictions on the position of substitution, as long as it is a position where a hydrogen atom can be substituted, and when two or more substitutions occur, the two or more substituents may be the same or different from each other.

[0027] In this specification, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the following: hydrogen; halogen group; cyano; nitro; hydroxyl; carbonyl; ester group; imide group; amide group; amino group; carboxyl group; sulfonic acid group; sulfonamide group; phosphine oxide group; alkoxy group; aryloxy group; alkyl thio group; aryl thio group; alkyl sulfonyl group; aryl sulfonyl group; silyl group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aryl-alkenyl group; alkyl aryl group; arylphosphyl group; or heterocyclic group containing one or more of N, O, and S atoms, or unsubstituted or substituted with two or more substituents linked together from the substituents exemplified above. For example, "substituents linked together from two or more substituents" can be biphenyl. That is, biphenyl can be interpreted as an aryl group or a substituent linked together from two phenyl groups.

[0028] In this instruction manual, or The term "bond" refers to a bond connected to other substituents, and "direct bond" refers to a bond in which there are no independent atoms in the portion represented by L.

[0029] Examples of halogen groups in this specification include fluorine, chlorine, bromine, or iodine.

[0030] In this specification, alkyl is a monovalent functional group derived from alkanes, which can be linear or branched, and the number of carbon atoms in linear alkyl groups is not particularly limited, but is preferably 1 to 20. In addition, the number of carbon atoms in branched alkyl groups is 3 to 20. Specific examples of alkyl groups include, but are not limited to, 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, and 2,6-dimethylheptane-4-yl. Alkyl groups may be substituted or unsubstituted, and in the case of substitution, examples of substituents are as described above.

[0031] In this specification, cycloalkyl is a monovalent functional group derived from cycloalkanes, which can be monocyclic or polycyclic and is not particularly limited, but has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 10 carbon atoms. Specifically, examples 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, and bicyclo[2,2,1]heptyl. The cycloalkyl group can be substituted or unsubstituted, and in the case of substitution, examples of substituents are as described above.

[0032] In this specification, alkoxy is a functional group terminally bonded to an ether group (-O-) of the aforementioned alkyl group, and the description of the alkyl group can be used, except that the alkoxy is a functional group bonded to an ether group (-O-). For example, it can be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but it is preferably 1 to 20. Specifically, examples include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, i-propoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, cycloheptoxy, benzyloxy, and p-methylbenzyloxy. Alkoxy groups can be substituted or unsubstituted.

[0033] In this specification, aryl is a monovalent functional group derived from aromatic hydrocarbons, which is not particularly limited, but preferably has 6 to 20 carbon atoms and can be monocyclic or polycyclic aryl. Monocyclic aryl can be phenyl, biphenyl, terphenyl, but is not limited to these. Polycyclic aryl can be naphthyl, anthraceneyl, phenanthryl, pyrene, etc. base, Aryl, fluorene, but not limited to these. Aryl groups can be substituted or unsubstituted, and in the case of substitution, examples of substituents are as described above.

[0034] In this specification, alkylene is a divalent functional group derived from an alkane, and the description of alkyl as described above can be used, except that alkylene is a divalent functional group. For example, it can be linear or branched, such as methylene, ethylene, propylene, isobutylene, sec-butylene, tert-butylene, pentylene, and hexylene. Alkylene can be substituted or unsubstituted, and in the case of substitution, examples of substituents are as described above.

[0035] In this specification, arylene is a divalent functional group derived from aromatic hydrocarbons, and the description of aryl groups described above can be applied, except that arylene is a divalent functional group. For example, it can include phenylene, biphenylene, terphenylene, naphthylene, fluorenyl, pyrene, phenanthrene, etc. alkyl, tetraphenyl, anthracene. The aryl group can be substituted or unsubstituted, and in the case of substitution, examples of substituents are as described above.

[0036] In this specification, cycloalkylene is a divalent functional group derived from cycloalkanes, and the above description of cycloalkylene can be applied, except that cycloalkylene is a divalent functional group. Cycloalkylene can be substituted or unsubstituted, and in the case of substitution, examples of substituents are as described above.

[0037] In this specification, "direct bond" means that there are no atoms or groups of atoms at the relevant position and that they are connected by a bond line.

[0038] According to one embodiment of the present 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 may be the same as or different from each other, and each is independently 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, and X3 may be the same as or different from each other, and each can be a direct bond, -O-, -COO-, -CONR9-, -O(CO)O-, or -NR independently. 10 (CO)NR 11 - one of them, and

[0048] R9 to R 11 They may be the same as or different from each other, each independently being one of hydrogen, alkyl, cycloalkyl, or aryl, and

[0049] A1, A2, B1, and B2 may be the same as or different from each other, and each is independently one of alkylene, cycloalkylene, or arylene.

[0050] n, m, p, and q may be the same or different from each other, each being an independent integer of 0 or 1, and at least one of n, m, p, and q is 1.

[0051] The inventors of this disclosure have experimentally determined that the compound represented by Formula 1 can be used as a crosslinking agent because, due to its chemical structure, it can react with electron-rich systems in heat or acid, and because the compound represented by Formula 1 has many crosslinking sites (8 sites), the tensile properties of the cured layer containing the compound represented by Formula 1 can be significantly improved, and the decrease in glass transition temperature can be suppressed, thus completing the present invention.

[0052] In the above chemical formula 1, R1 to R8 may be the same or different from each other, and each is independently one of alkyl, arylalkyl, or alkoxyarylalkyl. Arylalkyl means a functional group in which the hydrogen atom of the alkyl group is replaced by an aryl group. Furthermore, alkoxyarylalkyl means a functional group in which the hydrogen atom of the alkyl group is replaced by an alkoxyaryl group, and alkoxyaryl means a functional group in which the hydrogen atom of the aryl group is replaced by an alkoxy group.

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

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

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

[0056] Furthermore, in the above chemical formula 2, at least one of X1, X2, and X3 can be -O-, -COO-, -CONR9-, -O(CO)O-, or -NR. 10 (CO)NR 11One of the following: -O-, -COO-, -CONR9-, -O(CO)O-, or -NR-. 10 (CO)NR 11 One of them. This ensures molecular flexibility in terms of molecular structure, increases the stacking between polymer chains, significantly improves the tensile properties of the cured layer containing the compound represented by chemical formula 1, and suppresses the decrease in glass transition temperature.

[0057] In the above chemical formula 2, there are no particular restrictions on the specific instances of X1, X2, and X3, but for example, they can 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, if at least one of X1, X2, and X3 in chemical formula 2 is -NR 12 - (where R) 12 If the amino group is one of hydrogen, alkyl, cycloalkyl, alkoxyalkyl, or aryl, the manufacturing process becomes more complicated, and the reliability (especially heat resistance / moisture resistance) may decrease as the number of amino groups increases.

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

[0060] There are no particular limitations on specific examples of A1, A2, B1, and B2, but for example, they can be one of methylene, ethylene, n-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 in terms of molecular structure, enhances π-π interactions, significantly improves the tensile properties of cured layers containing compounds represented by Formula 1, and suppresses the decrease in glass transition temperature.

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

[0062] In the above chemical formula 2, (n+m+p+q) can be an integer from 2 to 4, or from 3 to 4, or 4. This ensures molecular flexibility in terms of molecular structure, enhances π-π interactions, significantly improves the tensile properties of the cured layer containing the compound represented by chemical formula 1, and suppresses the decrease in glass transition temperature.

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

[0064]

[0065]

[0066]

[0067] .

[0068] Furthermore, compounds represented by Formula 1 may include compounds represented by any of the following Formulas 1-1 to 1-12. However, specific examples of compounds represented by Formula 1 are not limited to compounds represented by any of the following Formulas 1-1 to 1-12.

[0069] [Chemical Formula 1-1]

[0070]

[0071] [Chemical Formula 1-2]

[0072]

[0073] [Chemical Formulas 1-3]

[0074]

[0075] [Chemical Formulas 1-4]

[0076]

[0077] [Chemical Formulas 1-5]

[0078]

[0079] [Chemical Formulas 1-6]

[0080]

[0081] [Chemical Formulas 1-7]

[0082]

[0083] [Chemical Formulas 1-8]

[0084]

[0085] [Chemical Formulas 1-9]

[0086]

[0087] [Chemical Formulas 1-10]

[0088]

[0089] [Chemical Formula 1-11]

[0090]

[0091] [Chemical Formula 1-12]

[0092] .

[0093] The formaldehyde index of the compound according to EPA Method 8315A is 38 ppm or less, 37 ppm or less, 32 ppm or less, 29 ppm or less, 26 ppm or less, 25 ppm or less, 24 ppm or less, 23 ppm or less, 21 ppm or less, 20 ppm or less, 19 ppm or less, 18 ppm or less, 17 ppm or less, 1 ppm or more, 1 ppm to 38 ppm, 1 ppm to 37 ppm, 1 ppm to 32 ppm, 1 ppm to 29 ppm, 1 ppm to 26 ppm, 1 ppm to 25 ppm, 1 ppm to 24 ppm, 1 ppm to 23 ppm, 1 ppm to 21 ppm, 1 ppm to 20 ppm, 1 ppm to 19 ppm, 1 ppm to 18 ppm, or 1 ppm to 17 ppm.

[0094] There are no particular limitations on the method used to measure the formaldehyde index according to EPA Method 8315A, and for example, it can be measured using EPA (Environmental Protection Agency) Method 8315A (SW-846).

[0095] Formaldehyde is a substance with a very pungent odor that irritates the nose and eyes and contains components harmful to humans and the natural environment. Recently, it has been suspected of being a carcinogen, attracting worldwide attention, and laws and regulations are being strengthened, requiring that formaldehyde not be included in the manufacturing process of compounds. Since the formaldehyde index is reduced to 38 ppm or less according to EPA Method 8315A, compounds from this embodiment can be synthesized into environmentally friendly compounds.

[0096] Meanwhile, according to another embodiment of the present invention, a method for preparing a compound is provided, comprising the steps of: reacting a compound represented by chemical formula 3 with dicyandiamide to produce a compound represented by chemical formula 4; reacting a compound represented by chemical formula 4 with formaldehyde to produce a compound represented by chemical formula 5; and reacting a compound represented by chemical formula 5 with an alcohol.

[0097] [Chemical Formula 3]

[0098]

[0099] [Chemical Formula 4]

[0100]

[0101] [Chemical Formula 5]

[0102]

[0103] In the above chemical formulas 3 to 5,

[0104] L is a functional group represented by the following chemical formula 2.

[0105] [Chemical Formula 2]

[0106]

[0107] In the above chemical formula 2,

[0108] X1, X2, and X3 may be the same as or different from each other, and each can be a direct bond, -O-, -COO-, -CONR9-, -O(CO)O-, or -NR independently. 10 (CO)NR 11 - one of them, and

[0109] R9 to R 11 They may be the same as or different from each other, each independently being one of hydrogen, alkyl, cycloalkyl, or aryl, and

[0110] A1, A2, B1, and B2 may be the same as or different from each other, and each is independently one of alkylene, cycloalkylene, or arylene.

[0111] n, m, p, and q may be the same or different from each other, each being an independent integer of 0 or 1, and at least one of n, m, p, and q is 1.

[0112] The content related to chemical formula 2 is incorporated into the above content regarding this implementation scheme.

[0113] In the step of reacting the compound represented by Formula 3 with dicyandiamide to produce the compound represented by Formula 4, a sufficient excess of dicyandiamide may be added compared to the compound represented by Formula 3 to ensure that the dicyandiamide reacts with all the terminal cyano groups of the compound represented by Formula 3.

[0114] Furthermore, in the step of reacting the compound represented by Formula 3 with dicyandiamide to produce the compound represented by Formula 4, the reaction between the compound represented by Formula 3 and dicyandiamide can be carried out under alkaline conditions. Examples of alkaline agents are not particularly limited, but KOH can be used, for example. Furthermore, the reaction between the compound represented by Formula 3 and dicyandiamide can be carried out under solvent conditions. Examples of solvents are not particularly limited, but 2-methoxyethanol can be used, for example.

[0115] Meanwhile, in the step of reacting the compound represented by chemical formula 4 with formaldehyde to produce the compound represented by chemical formula 5, a sufficient excess of formaldehyde may be added compared to the compound represented by chemical formula 4 to ensure that the formaldehyde reacts with all the terminal amino groups of the compound represented by chemical formula 4.

[0116] Furthermore, in the step of reacting the compound represented by Formula 4 with formaldehyde to produce the compound represented by Formula 5, the reaction between the compound represented by Formula 4 and formaldehyde can be carried out under alkaline conditions. Examples of alkaline substances are not particularly limited, but for example, NaHCO3 can be used.

[0117] In addition, in the step of reacting the compound represented by chemical formula 5 with an alcohol, the alcohol may include a compound represented by chemical formula 6.

[0118] [Chemical Formula 6]

[0119] R 13 -OH

[0120] In the above chemical formula 6,

[0121] R 13 It is one of alkyl, arylalkyl, or alkoxyarylalkyl.

[0122] In the above chemical formula 6, R 13 It can be one of alkyl, arylalkyl, or alkoxyarylalkyl. Arylalkyl means a functional group in which the hydrogen atom in the alkyl group is replaced by an aryl group. In addition, alkoxyarylalkyl means a functional group in which the hydrogen atom in the alkyl group is replaced by an alkoxyaryl group, and alkoxyaryl means a functional group in which the hydrogen atom in the aryl group is replaced by an alkoxy group.

[0123] Specifically, in chemical formula 6 above, R 13It can be one of an alkyl group having 1 to 5 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or an alkoxyarylalkyl group having 8 to 30 carbon atoms.

[0124] Furthermore, in the step of reacting the compound represented by Formula 5 with an alcohol, an alcohol in sufficient excess compared to the compound represented by Formula 5 may be added to ensure that the alcohol reacts with all the terminal hydroxyl groups of the compound represented by Formula 5.

[0125] Furthermore, in the step of reacting the compound represented by Formula 5 with an alcohol, the reaction between the compound represented by Formula 5 and the alcohol can be carried out under acidic conditions. There are no particular limitations on examples of acids, but HCl can be used, for example.

[0126] Furthermore, the reaction between the compound represented by Formula 5 and the alcohol can be carried out under solvent conditions. There are no particular limitations on examples of solvents, but toluene can be used, for example.

[0127] Furthermore, after the step of reacting the compound represented by chemical formula 5 with the alcohol, a neutralization step can be performed. Since the step of reacting the compound represented by chemical formula 5 with the alcohol is carried out under acidic conditions, a base can be added in the neutralization step, and there are no particular limitations on the examples of the base, but for example, NaOH can be used.

[0128] After the compound represented by chemical formula 1 of this embodiment is synthesized by the method for preparing compounds according to another embodiment, additional steps such as filtration or drying may be performed if necessary. The content related to the filtration and drying steps can be applied without limitation to various methods, equipment, and conditions widely used in the conventional field of compound synthesis.

[0129] Meanwhile, according to another embodiment of the present invention, a crosslinking agent comprising the compound of the embodiment can be provided.

[0130] Content relating to the compound is incorporated herein by reference to this embodiment. The various functional groups contained in the compound can form crosslinked structures with the functional groups contained in the polyimide during a heat- or acid-mediated curing process, and due to this crosslinked structure, it can form crosslinked structures with other adjacent polyimides. Therefore, a photosensitive resin composition containing the crosslinking agent of another embodiment can significantly improve tensile strength while maintaining high resistance to various chemicals and heat.

[0131] Meanwhile, according to another embodiment of the present invention, a photosensitive resin composition comprising the compound of the embodiment can be provided.

[0132] Content related to the compound is incorporated into the above description of this embodiment.

[0133] The photosensitive resin composition may also include a binder resin. There are no particular limitations on the binder resin, as long as it can exhibit properties such as strength and developability of the film made from the resin composition. However, as an example, polyimide or polyphenylene oxide can be used. Azole.

[0134] In addition, the photosensitive resin composition may also contain a photoinitiator. There are no particular limitations on the photoinitiator, as long as it is an initiator that generates free radicals upon exposure to light to initiate crosslinking, but for example, it may be one or more selected from benzophenone-based compounds, acetophenone-based compounds, diimidazole-based compounds, triazine-based compounds, and oxime-based compounds.

[0135] The photosensitive resin composition may also contain a solvent. Solvents, which are compounds known in the art to which this disclosure pertains and capable of forming a layer of the photosensitive resin composition, may be used without particular limitation. Non-limiting examples of solvents may be one or more compounds selected from esters, ethers, ketones, aromatic hydrocarbons, and sulfoxides.

[0136] In addition, the photosensitive resin composition may also contain one or more additives selected from antioxidants, photoinitiator enhancers, curing accelerators, adhesion promoters, surfactants, thermal polymerization inhibitors, ultraviolet absorbers, dispersants and leveling agents.

[0137] Furthermore, according to another embodiment of the present invention, a cured layer comprising a cured product of the photosensitive resin composition can be provided. The cured product refers to the material obtained through the curing process of the photosensitive resin composition of the other embodiment. Content related to the photosensitive resin composition is incorporated herein by reference to the other embodiment. The cured layer may comprise both an organic insulating film and a photosensitive pattern.

[0138] The cured layer exhibits excellent heat resistance and tensile properties and can be applied to insulating films in semiconductor devices, interlayer insulating films in redistribution layers, etc. Furthermore, the cured layer can be used as a photoresist, photoresist, top solder resist, etc.

[0139] Furthermore, according to another embodiment of the present invention, an electronic device comprising the cured layer of this embodiment can be provided. Content related to the cured layer is incorporated herein by reference to the other embodiment.

[0140] Electronic devices comprising organic insulating films or photosensitive patterns formed from photosensitive resin compositions containing compounds of the embodiments can achieve excellent performance, such as high resolution and high sensitivity, and exhibit excellent film properties and high mechanical properties, as well as excellent heat resistance, for example, the adhesion of the organic insulating film or photosensitive pattern can be firmly maintained without deterioration even when used for a long time or exposed to high temperature conditions for a long time.

[0141] Examples of electronic devices include semiconductor devices.

[0142] Beneficial effects

[0143] According to this disclosure, compounds with excellent heat resistance and tensile properties, as well as crosslinking agents, photosensitive resin compositions, cured layers, and electronic devices comprising the same, can be provided. Detailed Implementation

[0144] The invention will be described in more detail in the following embodiments. However, the following embodiments are merely illustrative examples of this disclosure, and the content of this disclosure is not limited to the following embodiments.

[0145] <Manufacturing Example 1>: Synthesis of Compounds 1 to 12

[0146] (1) Preparation of compound 1

[0147] Compound 1 was synthesized by the reaction shown in [Reaction Formula 1] below.

[0148] [Reaction Formula 1]

[0149]

[0150] In a 500 ml round-bottom flask, 8 g (0.1 mol) of succinate (SM1, CAS No.: 110-61-2), 17.6 g (1 mol, 2.1 equivalents) of dicyandiamide (CAS No.: 461-58-5), 0.56 g (0.01 mol, 0.1 equivalents) of KOH, and 80 ml of 2-methoxyethanol were added and refluxed for 12 hours. After the reaction was complete, the mixture was stirred further at room temperature for 1 hour, and the P1-2 compound was obtained by filtration.

[0151] In a 500 ml round-bottom flask, the obtained compound P1-2, 0.84 g (0.01 mol, 0.1 equivalent) of NaHCO3, and 80 ml (1 mol, 10 equivalent) of 35% formaldehyde aqueous solution were added and stirred at 80 °C for 12 hours. After the reaction was complete, 40 ml of acetonitrile was slowly added. After the reaction was complete, the mixture was stirred further at room temperature for 1 hour, and compound P1-1 was obtained by filtration.

[0152] In a 250 mL round-bottom flask, the obtained compound P1-1 and 80 mL of methanol were added and cooled to 5 °C. Then, 0.12 mL (0.01 mol, 0.1 equivalent) of 37% hydrochloric acid was added. After raising the temperature to room temperature, the mixture was stirred until completely dissolved. After the reaction was complete, 40 mL of 5% NaOH solution was slowly added. After stirring for 1 hour, a solid was formed. After filtration, the solid was dried in a vacuum oven at 80 °C to obtain 12 g of compound 1 (yield 12%).

[0153]

[0154] HRMS [M+H] + : 601.3381

[0155] (2) Preparation of compound 2

[0156] Compound 2 was synthesized by the reaction shown in [Reaction 2] below.

[0157] [Reaction 2]

[0158]

[0159] Specifically, as shown in [Reaction 2], 15 g of compound 2 (yield 21%) was obtained by the same method as in the preparation example of compound 1, except that 16 g (0.1 mol) of compound SM2 (CAS: 90872-59-6) was used instead of 8 g (0.1 mol) of succinate (SM1, CAS: 110-61-2).

[0160]

[0161] HRMS [M+H] + : 683.4162

[0162] (3) Preparation of compound 3

[0163] Compound 3 was synthesized by the reaction shown in [Reaction 3] below.

[0164] [Reaction 3]

[0165]

[0166] Specifically, as shown in [Reaction 3], 15 g of compound P3-1 was synthesized by the same method as in the preparation example of compound 1, except that 13 g (0.1 mol) of compound SM3 (CAS: 626-17-5) was used instead of 8 g (0.1 mol) of succinate (SM1, CAS: 110-61-2).

[0167] In a 250 mL round-bottom flask, the obtained P3-1 compound and 100 mL of ethanol were added and cooled to 5 °C. Then, 0.24 mL (0.02 mol, 0.2 equivalent) of 37% hydrochloric acid was added. After raising the temperature to room temperature, the mixture was stirred until completely dissolved. After the reaction was complete, 50 mL of 5% NaOH solution was slowly added. After stirring for 1 hour, a solid was formed. After filtration, the solid was dried in a vacuum oven at 80 °C to obtain 18.2 g of compound 3 (yield 24%).

[0168]

[0169] HRMS [M+H] + 761.4626

[0170] (4) Preparation of compound 4

[0171] Compound 4 was synthesized by the reaction shown in [Reaction 4] below.

[0172] [Reaction 4]

[0173]

[0174] Specifically, as shown in [Reaction 4], compound P4-1 was synthesized by the same method as in the preparation example of compound 1, except that 18 g (0.1 mol) of compound SM4 (CAS: 46289-40-1) was used instead of 8 g (0.1 mol) of succinate (SM1, CAS: 110-61-2).

[0175] In a 500 ml round-bottom flask, the obtained P4-1 compound and 100 ml isopropanol were added and cooled to 5°C, followed by the addition of 1.2 ml (0.1 mol, 1 equivalent) of 37% hydrochloric acid. After raising the temperature to room temperature, the mixture was stirred until completely dissolved. After the reaction was complete, 50 ml of 5% NaOH solution was slowly added. After stirring for 1 hour, a solid was formed. Following filtration, the solid was dried in a vacuum oven at 80°C to obtain 23 g of compound 4 (yield 25%).

[0176] In a 500 ml round-bottom flask, compound P4-1 was added together with 100 ml of isopropanol, cooled to 5°C, and then 1.2 ml (0.1 mol, 1 equivalent) of 37% hydrochloric acid was added. After raising the temperature to room temperature, the mixture was stirred until completely dissolved. After the reaction was complete, 50 ml of 5% NaOH solution was slowly added. After stirring for 1 hour, a solid was formed. After filtration, the solid was dried in a vacuum oven at 80°C to obtain 23 g (3 steps, 25% overall yield) of compound 4.

[0177]

[0178] HRMS [M+H] + : 923.6035

[0179] (5) Preparation of compound 5

[0180] Compound 5 was synthesized by the reaction shown in [Reaction 5] below.

[0181] [Reaction 5]

[0182]

[0183] Specifically, as shown in [Reaction 5], compound P5-1 was synthesized by the same method as in the preparation example of compound 1, except that 12.5 g (0.1 mol) of compound SM5 (CAS: 1656-48-0) was used instead of 8 g (0.1 mol) of succinate (SM1, CAS: 110-61-2).

[0184] In a 500 mL round-bottom flask, the obtained P5-1 compound, 138 g (1 mol, 10 equivalents) of 4-methoxybenzyl alcohol, 1.92 g (0.01 mol, 0.1 equivalents) of p-toluenesulfonic acid, and 280 mL of toluene were added and refluxed. After the reaction was complete, 140 mL of 5% NaOH solution was slowly added for neutralization. After extraction of the toluene layer, the solvent was removed to obtain an orange solid. Recrystallization from ethanol yielded 22 g of compound 5 (yield 15%).

[0185]

[0186] HRMS [M+H] + : 1493.6982

[0187] (6) Preparation of compound 6

[0188] Compound 6 was synthesized by the reaction shown in [Reaction 6] below.

[0189] [Reaction Formula 6]

[0190]

[0191] Specifically, as shown in [Reaction 6], 24 g of compound 6 (yield 30%) was obtained by the same method 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 succinate (SM1, CAS: 110-61-2).

[0192]

[0193] HRMS [M+H] + 799.4062

[0194] (7) Preparation of compound 7

[0195] Compound 7 was synthesized by the reaction shown in [Reaction 7] below.

[0196] [Reaction Formula 7]

[0197]

[0198] Specifically, as shown in [Reaction 7], compound P7-1 was synthesized by the same method as in the preparation example of compound 1, except that 24 g (0.1 mol) of compound SM7 (CAS: 90870-40-9) was used instead of 8 g (0.1 mol) of succinate (SM1, CAS: 110-61-2).

[0199] In a 500 mL round-bottom flask, the obtained P7-1 compound, 108 g (1 mol, 10 equivalents) of benzyl alcohol, 1.92 g (0.01 mol, 0.1 equivalents) of p-toluenesulfonic acid, and 220 mL of toluene were added and refluxed. After the reaction was complete, 110 mL of 5% NaOH solution was slowly added for neutralization. After extraction of the toluene layer, the solvent was removed to obtain a yellow solid. Recrystallization from ethanol yielded 36 g of compound 7 (yield 26%).

[0200]

[0201] HRMS [M+H] + : 1369.6258

[0202] (8) Preparation of compound 8

[0203] Compound 8 was synthesized by the reaction shown in [Reaction 8] below.

[0204] [Reaction Equation 8]

[0205]

[0206] As shown in [Reaction Equation 8], 30 g (0.25 mol) of 3-cyanophenol (SM8-1, CAS: 873-62-1), 20 g (0.12 mol, 0.5 equivalent) of carbonyl diimidazole (CDI, CAS: 530-62-1), 1.5 g (0.012 mol, 0.05 equivalent) 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 the reaction was complete, half of the solvent was removed, and 120 ml of ethanol was slowly added to form a solid, which was obtained by filtration to yield 28.2 g of compound SM8.

[0207] Subsequently, as shown in [Reaction Formula 8], compound P8-1 was synthesized by the same method as in the preparation example of compound 1, except that 26 g (0.1 mol) of compound SM8 was used instead of (0.1 mol) of succinate (SM1, CAS: 110-61-2).

[0208] In a 250 mL round-bottom flask, the obtained P8-1 compound and 200 mL of n-butanol were added, followed by 1.2 mL (0.1 mol, 1 equivalent) of 37% hydrochloric acid. After raising the temperature to room temperature, the mixture was stirred until completely dissolved. After the reaction was complete, 50 mL of 5% NaOH solution was slowly added. After stirring for 1 hour, a solid was formed. Following filtration, the solid was dried in a vacuum oven at 80 °C to obtain 12.3 g of compound 8 (yield 11%).

[0209]

[0210] HRMS [M+H] + : 1121.7288

[0211] (9) Preparation of compound 9

[0212] Compound 9 was synthesized by the reaction shown in [Reaction 9] below.

[0213] [Reaction Formula 9]

[0214]

[0215] Specifically, as shown in [Reaction Formula 9], 13.7 g of compound 9 (yield 20%) was obtained by the same method as in the preparation example of compound 1, except that 16.6 g (0.1 mol) of compound SM9 (CAS: 7253-99-8) was used instead of 8 g (0.1 mol) of succinate (SM1, CAS: 110-61-2).

[0216]

[0217] HRMS [M+H] + : 687.3851

[0218] (10) Preparation of compound 10

[0219] Compound 10 was synthesized by the reaction shown in [Reaction Formula 10] below.

[0220] [Reaction Formula 10]

[0221]

[0222] Specifically, as shown in [Reaction Formula 10], 15 g of compound P10-1 was synthesized by the same method as in the preparation example of compound 1, except that 26.2 g (0.1 mol) of compound SM10 (CAS: 1090685-75-8) was used instead of 8 g (0.1 mol) of succinate (SM1, CAS: 110-61-2).

[0223] In a 5000 ml round-bottom flask, the obtained compound P10-1 and 200 ml of n-propanol were added, followed by 1.2 ml (0.1 mol, 1 equivalent) of 37% hydrochloric acid. After raising the temperature to room temperature, the mixture was stirred until completely dissolved. After the reaction was complete, 50 ml of 5% NaOH solution was slowly added. After adding 50 ml of water and stirring for 1 hour, a solid was formed. After filtration, the solid was dried in a vacuum oven at 80 °C to obtain 18 g of compound 10 (yield 18%).

[0224]

[0225] HRMS [M+H] + : 1007.6252

[0226] (11) Preparation of compound 11

[0227] Compound 11 was synthesized by the reaction shown in [Reaction Formula 11] below.

[0228] [Reaction Formula 11]

[0229]

[0230] As shown in [Reaction 11], in a 250 ml round-bottom flask, 40 g (0.25 mol) of 4-cyanophenylacetic acid (SM11-1, CAS: 5462-71-5), 36 g (0.25 mol, 1 equivalent) of 4-(ethylamino)benzyl nitrile (CAS: 4714-63-0), 1.5 g (0.012 mol, 0.05 equivalent) of N,N-dimethylaminopyridine (DMAP), and 160 ml of chloroform (CHCl3) were added, followed by the slow addition of 52.8 g (0.28 mol, 1.1 equivalent) of EDC·HCl·2H2O. The reaction was terminated after stirring at room temperature for 12 hours. Post-treatment was performed using a saturated NH4Cl solution. After removing all CHCl3, 120 ml of ethanol was added and stirred. The resulting solid was obtained by filtration to yield 54.2 g of the SM11 compound.

[0231] Subsequently, as shown in [Reaction Formula 11], compound P11-1 was synthesized by the same method as in the preparation example of compound 1, except that 28.9 g (0.1 mol) of compound SM11 was used instead of (0.1 mol) of succinate (SM1, CAS: 110-61-2).

[0232] In a 250 ml round-bottom flask, the obtained compound P11-1 and 100 ml of ethanol were added, followed by 0.24 ml (0.02 mol, 0.2 equivalents) of 37% hydrochloric acid. After raising the temperature to room temperature, the mixture was stirred until completely dissolved. After the reaction was complete, 50 ml of 5% NaOH solution was slowly added for neutralization. After stirring for 1 hour, a solid was formed. After filtration, the solid was dried in a vacuum oven at 80 °C to obtain 24 g of compound 11 (yield 26%).

[0233]

[0234] HRMS [M+H] + : 922.5466

[0235] (12) Preparation of compound 12

[0236] Compound 12 was synthesized by the reaction shown in [Reaction Formula 12] below.

[0237] [Reaction 12]

[0238]

[0239] Specifically, as shown in [Reaction 12], 14.8 g of compound 12 (yield 22%) was obtained by the same method as in the preparation example of compound 1, except that 15.6 g of SM12 (CAS: 39095-25-5) compound was used instead of 8 g (0.1 mol) of succinate (SM1, CAS: 110-61-2).

[0240]

[0241] HRMS [M+H] + : 677.3685

[0242] <Manufacturing Example 2>: Synthesis of Compounds C1 to C2

[0243] (1) Preparation of compound C1

[0244] Compound C1 is synthesized by the reaction shown in the following [reaction formula C1].

[0245] [Reaction formula C1]

[0246]

[0247] Specifically, as shown in [Reaction C1], 18 g of compound C1 (yield 22%) was obtained by the same method 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 succinate (SM1, CAS: 110-61-2).

[0248]

[0249] HRMS [M+H] + 364.1937

[0250] (2) Preparation of compound C2

[0251] Compound C2 is synthesized by the reaction shown in [reaction formula C2] below.

[0252] [Reaction formula C2]

[0253]

[0254] Specifically, as shown in [Reaction C2], 12.3 g (0.1 mol) of melamine (SM13, CAS: 108-78-1), 0.84 g (0.01 mol, 0.1 equivalent) of NaHCO3, and 40 ml (1 mol, 5 equivalent) of 35% formaldehyde aqueous solution were added to a 250 ml round-bottom flask and stirred at 80 °C for 12 hours. After the reaction was complete, water was removed by vacuum distillation, and the remaining solid (C2-1) was used for subsequent reactions.

[0255] The obtained C2-1 compound was added, along with 80 ml of methanol, and the mixture was cooled to 5°C. Then, 0.24 ml (0.02 mol, 0.2 equivalent) of 37% hydrochloric acid was added. After raising the temperature to room temperature, the mixture was stirred until completely dissolved. After the reaction was complete, 40 ml of 5% NaOH solution was slowly added. After stirring for 1 hour, a solid was formed. Following filtration, the solid was recrystallized twice with methanol / water (50 ml / 50 ml) to obtain 5.5 g of compound C2 (yield 8.3%).

[0256]

[0257] HRMS [M+H] + : 661.3664

[0258] <Manufacturing Example 3>: Synthesis of Polyimide Resin

[0259] In a round-bottom flask, 14.4 g (0.31 mol) of 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane (Bis-AP-AF) was dissolved in 500 g of propylene glycol monomethyl ether acetate (PGMEA) at 60 °C. Then, 91.1 g (0.29 mol) of 4,4'-oxyphthalic anhydride (ODPA) was added and the mixture was stirred for 2 hours, followed by the addition of 7.2 g (0.03 mol) of phthalic anhydride as a capping agent and stirring for another 2 hours. The temperature was then raised to 170 °C and stirred for 6 hours. Afterward, the mixture was cooled to room temperature. The weight-average molecular weight (Mw) of polymeric resin A, measured by gel permeation chromatography (GPC), was 15,000 g / mol, and the degree of imidization (DOI) of resin A, measured by infrared spectroscopy (IR), was 93%. The weight-average molecular weight of polymeric resin A was measured by gel permeation chromatography in tetrahydrofuran (THF) solvent.

[0260] <Manufacturing Example 4>: Preparation of Photosensitive Resin Composition

[0261] The photosensitive resin composition was prepared by mixing and stirring the components described in Tables 1 and 2 below for 24 hours. The values ​​in Tables 1 and 2 are weight percentages of each component based on 100% by weight (solids content) of polyimide resin.

[0262] [Table 1]

[0263]

[0264] [Table 2]

[0265]

[0266] In Tables 1 and 2 above,

[0267] MIPHOTO PAC425 refers to NAC5 ester containing 2,3,4,4'-tetrahydroxybenzophenone from Miwon Commercial Co., Ltd., and

[0268] PETG refers to pentaerythritol tetraglycidyl ether.

[0269] <Experimental Example>

[0270] The properties of the compounds or cured layers obtained in the examples and comparative examples were measured using the following methods, and the results are shown in Table 3.

[0271] 1. Formaldehyde Index

[0272] The formaldehyde index of the compounds obtained in the examples and comparative examples was measured according to EPA (Environmental Protection Agency) Method 8315A (SW-846).

[0273] 2. Young's modulus, tensile strength, and elongation.

[0274] The photosensitive resin composition of Preparation Example 4 was spin-coated onto a 6-inch wafer to form a film. The solvent was evaporated at 120°C for 2 minutes to allow initial curing. It was then finally cured at 180°C for 2 hours in a nitrogen atmosphere oven (Koyo INH oven), resulting in a final cured layer thickness of 10 μm. To separate the cured layer from the wafer, it was immersed in 2.5% HF diluted with DI water (deionized water) for 30 minutes. While the film was floating, it was removed and washed three times with distilled water (DI water). The obtained cured layer was dried in a convection oven at 40°C for 1 hour and then cut into 10 cm × 1 cm pieces to prepare samples for property measurement.

[0275] The prepared samples were placed in a UTM (Universal Testing Machine, Zwick) at 25°C, and Young's modulus, tensile strength, and elongation were measured. The sample measurement length was set to 1 cm × 5 cm, the tensile speed to 10.0 mm / min, and the load cell to 0.5 kN.

[0276] 3. Glass transition temperature (Tg) and coefficient of thermal expansion (CTE)

[0277] The photosensitive resin composition of Preparation Example 4 was spin-coated onto a 6-inch wafer to form a film. The solvent was evaporated at 120°C for 2 minutes to allow initial curing. It was then finally cured at 180°C for 2 hours in a nitrogen atmosphere oven (Koyo INH oven), resulting in a final cured layer thickness of 10 μm. To separate the cured layer from the wafer, it was immersed in 2.5% HF diluted with DI water (deionized water) for 30 minutes. While the film was floating, it was removed and washed three times with distilled water (DI water). The obtained cured layer was dried in a convection oven at 40°C for 1 hour and then cut into 10 cm × 1 cm pieces to prepare samples for property measurement.

[0278] The prepared sample was heated in a nitrogen atmosphere from 25°C at a rate of 10°C / min using a TA Q400 instrument to measure the glass transition temperature and coefficient of thermal expansion.

[0279] [Table 3]

[0280] Experimental results

[0281]

[0282] As shown in Table 1, it was confirmed that the compounds of the examples had a lower formaldehyde index compared to the comparative examples. Furthermore, it was confirmed that the cured layer using the compounds of the examples exhibited superior mechanical and thermal properties compared to the comparative examples.

Claims

1. A compound represented by the following Chemical Formula 1: [Chemical Formula 1] ###0001### In the above Chemical Formula 1, R1 to R8 are the same as or different from each other, each independently one of an alkyl group, an arylalkyl group, or an alkoxyarylalkyl group, and L is a functional group represented by the following Chemical Formula 2, [Chemical Formula 2] ###0002### In the above Chemical Formula 2, X1, X2, X3, equal to or different from each other, are each independently a direct bond, -O-, -COO-, -CONR9-, -O(CO)O-, or -NR 10 (CO)NR 11 - one of the following: R9to R 11 each independently of one another, hydrogen, alkyl, cycloalkyl, or aryl, and A1, A2, B1, and B2 are the same as or different from each other, each independently one of an alkylene group, a cycloalkylene group, or an arylene group, and n, m, p, and q are the same as or different from each other, each independently an integer of 0 or 1, and at least one of n, m, p, and q is 1.

2. The compound according to claim 1, wherein A1, A2, B1, and B2 are the same as or different from each other, each independently one of a methylene group, an ethylene group, a n-propylene group, a 1,3-butane diyl group, a cyclohexylene group, a 1,3-phenylene group, a 5-methyl-1,3-phenylene group, a 2,5-dimethyl-1,4-phenylene group, a 1,5-naphthylene group, or a 1,6-naphthylene group.

3. The compound according to claim 1, wherein the functional group represented by the Chemical Formula 2 is selected from any one of the following: 。 4. The compound of claim 1, wherein at least one of X1, X2, X3 in the chemical formula 2 is -0-, -COO-, -CONR9-, -0(CO)0-, or -NR 10 (CO)NR 11 - one of -0-, -COO-, -CONR9-, -0(CO)0-, or -NR 5. The compound according to claim 1, wherein R9 is one of hydrogen, a methyl group, or an ethyl group.

6. The compound of claim 1, wherein R 10 and R 11 are each independently one of hydrogen or methyl.

7. The compound according to claim 1, wherein (n+m+p+q) in the Chemical Formula 2 is an integer of 2 to 4.

8. The compound according to claim 1, wherein in the Chemical Formula 1, R1 to R8 are the same as or different from each other, each independently one of an alkyl group having 1 to 5 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or an alkoxyarylalkyl group having 8 to 30 carbon atoms.

9. The compound according to claim 1, wherein in the Chemical Formula 1, R1 to R8 are the same as or different from each other, each independently one of a methyl group, an ethyl group, a n-propyl group, an iso-propyl group, a n-butyl group, a benzyl group, or a 4-methoxybenzyl group.

10. The compound according to claim 1, wherein in the Chemical Formula 1, R1 to R8 are the same.

11. The compound according to claim 1, wherein the compound represented by the Chemical Formula 1 includes a compound represented by any one of Chemical Formulae 1-1 to 1-12: [Chemical Formula 1-1] ###0003### [Chemical Formula 1-2] ###0004### [Chemical Formula 1-3] ###0005### [Chemical Formula 1-4] ###0006### [Chemical Formula 1-5] ###0007### [Chemical Formula 1-6] ###0008### [Chemical Formula 1-7] ###0009### [Chemical Formula 1-8] ###0010### [Chemical Formula 1-9] ###0011### [Chemical Formula 1-10] ###0012### [Chemical Formula 1-11] ###0013### [Chemical Formula 1-12] ###0014### 。 12. The compound according to claim 1, wherein a formaldehyde index according to EPA Method 8315A is 38 ppm or less.

13. A method for preparing a compound comprising the steps of: reacting a compound represented by Chemical Formula 3 with dicyandiamide to produce a compound represented by Chemical Formula 4; reacting the compound represented by Chemical Formula 4 with formaldehyde to produce a compound represented by Chemical Formula 5; and reacting the compound represented by Chemical Formula 5 with an alcohol: [Chemical Formula 3] ###0015### [Chemical Formula 4] ###0016### [Chemical Formula 5] ###0017### In the above Chemical Formulae 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, equal to or different from each other, are each independently a direct bond, -O-, -COO-, -CONR9-, -O(CO)O-, or -NR 10 (CO)NR 11 - one of the following: R9to R 11 each independently of one another, hydrogen, alkyl, cycloalkyl, or aryl, and A1, A2, B1, and B2 are the same as or different from each other, and each is independently one of an alkylene group, a cycloalkylene group, or an arylene group, and n, m, p, and q are the same as or different from each other, and each is independently an integer of 0 or 1, and at least one of n, m, p, and q is 1.

14. The method of claim 13, wherein the alcohol comprises 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 according to claim 1.

16. A photosensitive resin composition comprising the compound according to claim 1.

17. A cured layer comprising a cured product of the photosensitive resin composition according to claim 16.

18. An electronic device comprising the cured layer according to claim 17.

Images