Naphthalenevinylpyridine compounds, photosensitive resin compositions, their applications and patterning methods

Abstract

This invention provides a naphthylvinylpyridine compound, a photosensitive resin composition, its application, and a method for patterning. The naphthylvinylpyridine compound has the structure shown in the formula. The absorption band of the above-mentioned naphthylvinylpyridine compound is in the 380–440 nm range, making it particularly suitable for use as a sensitizer in photocuring systems, which can significantly improve the photosensitivity of the photocuring system. When the above-mentioned naphthylvinylpyridine compound is used as a sensitizer in a photosensitive resin composition, the composition exhibits higher photosensitivity, higher resolution, and higher adhesion.

Description

Technical Field

[0001] This invention relates to the field of photoresist technology, and more specifically, to a naphthylvinylpyridine compound, a photosensitive resin composition, its application, and a method for patterning. Background Technology

[0002] With the miniaturization of wiring spacing in printed circuit boards (PCBs) in recent years, dry film resists require high resolution to manufacture narrow-pitch patterns with high yield. Therefore, as the density requirements of PCBs increase, the contact area between the circuitry and the substrate becomes smaller, leading to increasingly higher demands for photosensitive resin compositions capable of forming resist patterns with excellent resolution and adhesion. Furthermore, from a productivity perspective, high photosensitivity of the photosensitive resin is also required.

[0003] As a method for forming photoresist patterns, the direct drawing exposure method, which directly draws photoresist patterns without using photomask patterns, has attracted attention. It is believed that based on this direct drawing exposure method, highly productive and high-resolution photoresist patterns can be formed.

[0004] Consequently, laser-based direct patterning exposure methods have developed rapidly in recent years. As a light source for maskless exposure, light with wavelengths of 350–410 nm is mostly used, especially i-rays (365 nm) or h-rays (405 nm). Therefore, the ability to form high-sensitivity, high-resolution resist patterns using light sources in these wavelength ranges, particularly h-rays, has become increasingly important. Correspondingly, the demand for photosensitive resin compositions capable of forming resist patterns with high sensitivity, high resolution, and excellent adhesion is increasing. Summary of the Invention

[0005] The main objective of this invention is to provide a naphthylvinylpyridine compound, a photosensitive resin composition, and a patterning method to solve the problem that photosensitive resin compositions in the prior art are difficult to simultaneously possess excellent photosensitivity, resolution, and adhesion.

[0006] To achieve the above objectives, according to one aspect of the present invention, a naphthylvinylpyridine compound is provided, having a structure as shown in general formula I:

[0007]

[0008] Among them, R 1 R 2 Each can be independently represented by a halogen, nitro, cyano, or C1-C2 group. 20 Alkyl groups, C1-C 10 alkoxy groups, C1-C 10 alkyl ester group, C1-C 20The alkylamine group contains any one or more groups, and the methylene group in each group may optionally be replaced by an oxygen, sulfur, or imine group; a represents any integer from 0 to 4, b represents any integer from 0 to 3, and when a is greater than or equal to 2, multiple existing R groups are allowed. 1 Each can be the same or different; when b is greater than or equal to 2, multiple existing R 2 They can be the same or different; m represents any integer from 2 to 3, n represents any integer from 2 to 3, and m and n can be the same or different.

[0009] Furthermore, R 1 R 2 Each can be independently classified as fluorine-based, chlorine-based, bromine-based, nitro-based, cyanine-based, or C1-C2. 10 Alkyl groups, C1-C6 alkoxy groups, C1-C6 alkoxy groups 10 It can be any one or more groups selected from alkylamine groups and C1 to C6 alkyl ester groups.

[0010] Furthermore, a and b each independently represent any integer from 0 to 2.

[0011] Furthermore, in general formula I, R 1 R 2 Each group independently represents methoxy, ethoxy, propoxy, chloro, bromo, methyl, ethyl, isopropyl, dimethylamino, nitro, methyl ester, or cyano, where m and n are 2 or 3, and a and b are 0, 1, or 2; preferably, the naphthylvinylpyridine compounds are selected from any one of the following compounds:

[0012]

[0013]

[0014] Furthermore, in general formula I, R 1 R 2 Each group independently represents a chlorine group and / or a bromine group, m and n are 2 or 3, and a and b are 0 or 1; preferably, the naphthylvinylpyridine compound is selected from any one of the following compounds:

[0015]

[0016] To achieve the above objectives, according to one aspect of the present invention, a photosensitive resin composition is provided, comprising component A, component B, component C and component D, wherein component A is an alkali-soluble polymer, component B is a compound having olefinic unsaturated double bonds, component C is a first sensitizer, and component D is a photoinitiator and / or a second sensitizer, wherein the first sensitizer includes the aforementioned naphthylvinylpyridine compounds, and the second sensitizer is of a different type than the first sensitizer.

[0017] Furthermore, in the photosensitive resin composition, the weight content of the first sensitizer is 0.001 to 10%, preferably 0.005 to 5%.

[0018] Further, the alkali-soluble polymer is selected from one or more of the group consisting of (meth)acrylate polymers, styrene polymers, epoxy polymers, aliphatic polyurethane (meth)acrylate polymers, aromatic polyurethane (meth)acrylate polymers, amide resins, amide epoxy resins, alkyd resins, and phenolic resins; preferably, the alkali-soluble polymer is selected from one or more of the group consisting of epoxy polymers, aliphatic polyurethane (meth)acrylate polymers, aromatic polyurethane (meth)acrylate polymers, amide resins, amide epoxy resins, alkyd resins, and phenolic resins; preferably, the weight content of the alkali-soluble polymer in the photosensitive resin composition is 20-70%, more preferably 30-60%; preferably, the molecular weight distribution of the alkali-soluble resin is 1.5-6.0, more preferably 2.6-3.8.

[0019] Furthermore, compounds having olefinic unsaturated double bonds include compounds obtained by reacting α,β-unsaturated carboxylic acids with polyols, bisphenol A-type (meth)acrylate compounds, compounds obtained by reacting α,β-unsaturated carboxylic acids with compounds containing glycidyl groups, (meth)acrylate compounds with intramolecular urethane bonds, nonylphenoxypolyethyleneoxyacrylates, γ-chloro-β-hydroxypropyl-β'-(meth)acryloyloxyethyl-phthalate, β-hydroxyethyl-β'-(meth)acryloyloxyethyl-phthalate One or more of the following groups are included in the group consisting of dicarboxylate, β-hydroxypropyl-β'-(meth)acryloyloxyethyl-phthalate, phthalic acid compounds, and alkyl (meth)acrylates, preferably compounds having olefinic unsaturated double bonds selected from any one or more of bisphenol A (meth)acrylate compounds and / or (meth)acrylate compounds having intramolecular urethane bonds; preferably, the weight content of the compound having olefinic unsaturated double bonds in the photosensitive resin composition is 20-50%, more preferably 25-45%.

[0020] Further, component D includes one or more of the following: imidazolium compounds, acridine compounds, aromatic ketone compounds, anthraquinone compounds, benzoin and benzoin alkyl ether compounds, oxime ester compounds, triazine compounds, coumarin compounds, and thioxanthone compounds; preferably, the weight content of component D in the photosensitive resin composition is 0.01 to 10%; more preferably, component D includes one or more of the following: imidazolium compounds, acridine compounds, aromatic ketone compounds, anthraquinone compounds, benzoin and benzoin alkyl ether compounds, oxime ester compounds, triazine compounds, coumarin compounds, and thioxanthone compounds; more preferably, component D includes one or more of the following: imidazolium compounds, oxime ester compounds, triazine compounds, and thioxanthone compounds.

[0021] Furthermore, the photosensitive resin composition also includes additives, which include one or more of hydrogen donors, dyes, pigments, photochromic agents, fillers, plasticizers, stabilizers, coating aids, and release accelerators. Preferably, the weight content of the additives in the photosensitive resin composition is 1 to 10%.

[0022] According to another aspect of the present invention, a photosensitive resin laminate is provided, the photosensitive resin laminate comprising a photosensitive resin layer formed from the above-described photosensitive resin composition.

[0023] According to another aspect of the present invention, a patterning method is provided, the patterning method comprising: patterning a photosensitive resin composition to obtain a mask, wherein the photosensitive resin composition is the aforementioned photosensitive resin composition.

[0024] Furthermore, the graphical method is used in the patterning process of manufacturing printed circuit boards, protective patterns, conductor patterns, lead frames, or semiconductor packages.

[0025] The above-mentioned naphthylvinylpyridine compounds have an absorption band of 380–440 nm, making them particularly suitable for use as sensitizers in photocuring systems, which can significantly improve the photosensitivity of the photocuring system. When the above-mentioned naphthylvinylpyridine compounds are used as sensitizers in photosensitive resin compositions, the compositions exhibit higher photosensitivity, higher resolution, and higher adhesion. Detailed Implementation

[0026] It should be noted that, unless otherwise specified, the embodiments and features described in this application can be combined with each other. The present invention will now be described in detail with reference to the embodiments.

[0027] As described in the background section of this application, the requirements for photosensitivity, resolution, and adhesion of photosensitive resin compositions for forming resist patterns in the prior art are increasing. It is difficult for photosensitive resin compositions in the prior art to simultaneously possess excellent photosensitivity, resolution, and adhesion. In order to solve this problem, this application provides a naphthylvinylpyridine compound, a photosensitive resin composition, and a patterning method.

[0028] In one typical embodiment of this application, a naphthylvinylpyridine compound is provided, which has a structure as shown in general formula I:

[0029]

[0030] Among them, R 1 R 2 Each can be independently represented by a halogen, nitro, cyano, or C1-C2 group. 20 Alkyl groups, C1-C 10 alkoxy groups, C1-C 10 alkyl ester group, C1-C 20 The alkylamine group contains any one or more groups, and the methylene group in each group may optionally be replaced by an oxygen, sulfur, or imine group; a represents any integer from 0 to 4, b represents any integer from 0 to 3, and when a is greater than or equal to 2, multiple existing R groups are allowed. 1 Each can be the same or different; when b is greater than or equal to 2, multiple existing R 2 They can be the same or different; m represents any integer from 2 to 3, and n represents any integer from 2 to 3. m and n can be the same or different.

[0031] The above-mentioned naphthylvinylpyridine compounds having general formula I have an absorption band in the 380-440 nm range, making them particularly suitable for use as sensitizers in photocuring systems, significantly improving the photosensitivity of the system. When these naphthylvinylpyridine compounds are used as sensitizers in photosensitive resin compositions, the compositions exhibit higher photosensitivity, higher resolution, and better adhesion. Especially compared to other substituents such as hydroxyl and amino groups, the above-mentioned R... 1 R 2 Each can be independently represented by a halogen, nitro, cyano, or C1-C2 group. 20 Alkyl groups, C1-C 10 alkoxy groups, C1-C 10 alkyl ester group, C1-C 20The alkylamine group contains any one or more groups, and the methylene group in each group may optionally be replaced by oxygen, sulfur, or imine groups. The corresponding naphthylvinylpyridine compounds have a more significant effect on improving the photosensitivity, resolution, and adhesion of the photosensitive resin composition.

[0032] For the purpose of further improving the photosensitivity of the photosensitive resin composition, R is preferred. 1 R 2 Each can be independently classified as fluorine-based, chlorine-based, bromine-based, nitro-based, cyanine-based, or C1-C2. 10 Alkyl groups, C1-C6 alkoxy groups, C1-C6 alkoxy groups 10 It can be any one or more groups selected from alkylamine groups and C1 to C6 alkyl ester groups.

[0033] To improve the yield of the target product in the preparation of naphthylvinylpyridine compounds, it is preferable that a and b each independently represent any integer from 0 to 2. Preferably, in general formula I, R... 1 R 2 Each can be independently represented as methoxy, ethoxy, propoxy, chloro, bromo, methyl, ethyl, isopropyl, dimethylamino, nitro, methyl ester, or cyano, with m and n being 2 or 3, and a and b being 0, 1, or 2.

[0034] In a preferred embodiment, the naphthylvinylpyridine compound is selected from any one of the following compounds:

[0035]

[0036]

[0037] For the purpose of further improving the photosensitivity of the photosensitive resin composition, in a more preferred embodiment, in general formula I, R 1 R 2 Each group independently represents a chlorine group and / or a bromine group, with m and n being 2 or 3, and a and b being 0 or 1. This is in contrast to C1–C6 alkoxy groups and C1–C6 alkoxy groups. 10 The alkylamine group, more preferably the above-mentioned R in this invention. 1 R 2 Each group independently represents a chlorine group and / or a bromine group, which can not only improve the photosensitivity of the photosensitive resin composition, but also have better synergistic effects with components A, B, C and D. For example, naphthylvinylpyridine compounds are selected from any of the following compounds:

[0038]

[0039] The following is an illustrative description of the preparation method of the naphthylvinylpyridine compounds of the present invention, which includes the following steps:

[0040] Raw material 1, raw material 2, and ammonium acetate were reacted in glacial acetic acid at 30–120°C for 2–20 h to obtain product 3 (which is the naphthylvinylpyridine compound of the present invention). The reaction route is shown below:

[0041]

[0042] In another typical embodiment of this application, a photosensitive resin composition is provided, comprising component A, component B, component C and component D, wherein component A is an alkali-soluble polymer, component B is a compound having olefinic unsaturated double bonds, component C is a first sensitizer, and component D is a photoinitiator and / or a second sensitizer, wherein the first sensitizer includes the aforementioned naphthylvinylpyridine compounds, and the second sensitizer is of a different type than the first sensitizer.

[0043] Because the above-mentioned naphthylvinylpyridine compounds having general formula I have an absorption band of 380–440 nm, they are particularly suitable for use as sensitizers in photocuring systems, and can greatly improve the photosensitivity of the photocuring system. When the above-mentioned naphthylvinylpyridine compounds are used as sensitizers in photosensitive resin compositions, the compositions exhibit high photosensitivity, high resolution, and high adhesion.

[0044] If the content of the first sensitizer is too small, there is a defect of decreased photosensitivity; if the content of the first sensitizer is too large, there is a defect of the photoresist pattern tending to widen beyond the photomask linewidth. To give the photosensitive resin composition more favorable photosensitivity for application, it is preferable that the weight content of the first sensitizer in the photosensitive resin composition is 0.001–10%, more preferably 0.005–5%, and even more preferably 0.1–0.5%. Limiting the amount of the first sensitizer within the above range is beneficial to improving the photosensitivity and resolution of the photocurable composition.

[0045] Alkali-soluble polymers can impart film-forming properties to photosensitive resin compositions. In a preferred embodiment, the alkali-soluble polymer is selected from one or more of the group consisting of (meth)acrylate polymers, styrene polymers, epoxy polymers, aliphatic polyurethane (meth)acrylate polymers, aromatic polyurethane (meth)acrylate polymers, amide resins, amide epoxy resins, alkyd resins, and phenolic resins.

[0046] In a preferred embodiment, the above-mentioned alkali-soluble polymer can be obtained by free radical polymerization of polymerizable monomers. Polymerizable monomers include, but are not limited to: polymerizable styrene derivatives such as styrene, vinyltoluene, α-methylstyrene, p-methylstyrene, p-ethylstyrene, and p-chlorostyrene, which are substituted at the α-position or on an aromatic ring; acrylamide derivatives such as acrylamide and diacetone acrylamide; ether derivatives of vinyl alcohols such as acrylonitrile and vinyl n-butyl ether; (meth)acrylic acid, α-bromo(meth)acrylic acid, α-chloro(meth)acrylic acid, β-furanyl(meth)acrylic acid, and β-styryl(meth)acrylic acid derivatives; alkyl (meth)acrylates, benzyl (meth)acrylates, phenoxyethyl methacrylate, tetrahydrofurfuryl (meth)acrylate, and (meth)acrylic acid... Dimethylaminoethyl ester, diethylaminoethyl (meth)acrylate, glycidyl (meth)acrylate, 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3-tetrafluoropropyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, glycidyl (meth)acrylate, and other (meth)acrylate compounds; maleic acid, maleic anhydride, monomethyl maleate, monoethyl maleate, monoisopropyl maleate, and other maleic acid monoesters; fumaric acid, cinnamic acid, α-cyanocinonic acid, itaconic acid, crotonic acid, propionic acid, N-vinylcaprolactam; N-vinylpyrrolidone, etc. These polymerizable monomers can be used alone or in combination of two or more.

[0047] From the perspective of alkali developability and adhesion, in order to improve the alkali developability and adhesion of alkali-soluble polymers, it is preferable to use alkali-soluble polymers containing carboxyl groups. The aforementioned alkali-soluble polymers containing carboxyl groups include, but are not limited to: acrylic resins containing (meth)acrylic acid as monomer units, which introduce carboxyl groups by using (meth)acrylic acid as monomer units; copolymers that further contain alkyl methacrylates as monomer units in addition to (meth)acrylic acid; and copolymers that further contain polymerizable monomers other than (meth)acrylic acid and alkyl methacrylates (such as monomers with vinyl unsaturated groups) as monomer components in addition to (meth)acrylic acid.

[0048] In another preferred embodiment, the carboxyl-containing alkali-soluble polymer can be obtained by free radical polymerization of a carboxyl-containing polymerizable monomer with other polymerizable monomers, particularly (meth)acrylate polymers copolymerized from (meth)acrylates, vinyl unsaturated carboxylic acids and other copolymerizable monomers.

[0049] The aforementioned (meth)acrylates include, but are not limited to: methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, pentyl methacrylate, hexyl methacrylate, heptyl methacrylate, octyl methacrylate, 2-ethylhexyl methacrylate, nonyl methacrylate, decyl methacrylate, undecyl methacrylate, dodecyl methacrylate, cyclohexyl methacrylate, benzyl methacrylate, diethylaminoethyl methacrylate, dimethylaminoethyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, furfuryl methacrylate, glycidyl methacrylate, etc. These (meth)acrylates can be used alone or in combination of two or more.

[0050] The aforementioned vinyl unsaturated carboxylic acids include, but are not limited to: acrylic acid, methacrylic acid, butenoic acid, maleic acid, fumaric acid, and itaconic acid, with acrylic acid and methacrylic acid being preferred. These vinyl unsaturated carboxylic acids can be used alone or in combination of two or more.

[0051] Other copolymerizable monomers mentioned above include, but are not limited to: (meth)acrylamide, (meth)acrylate, styrene, vinylnaphthalene, (meth)acrylonitrile, vinyl acetate, vinylcyclohexane, etc. These other copolymerizable monomers can be used alone or in combination of two or more.

[0052] The aforementioned alkali-soluble polymers can be used alone or in combination of two or more. Combinations of two or more alkali-soluble polymers can include those composed of different copolymer components, those with different weight-average molecular weights, and those with different dispersities.

[0053] In the photosensitive resin composition of the present invention, there is no particular limitation on the weight-average molecular weight of the alkali-soluble polymer, which should be adapted to the specific application environment. Considering both mechanical strength and alkali developability, to further improve the alkali developability of the alkali-soluble polymer and its mechanical strength after film formation, preferably, the weight-average molecular weight of the alkali-soluble polymer is 15,000 to 200,000, more preferably 30,000 to 150,000, and particularly preferably 30,000 to 120,000. When the weight-average molecular weight is greater than 15,000, the resistance to developer after exposure tends to be further improved; when the weight-average molecular weight is less than 200,000, the development time tends to be shorter, and compatibility with other components such as photoinitiators can be maintained. The weight-average molecular weight of the alkali-soluble polymer is determined by gel permeation chromatography (GPC) and obtained by conversion using a standard curve of standard polystyrene.

[0054] From the perspective of good alkaline developability, when the acid value of the alkali-soluble resin is low, the developing speed of the alkali-soluble resin is slow; when the acid value is high, the adhesion of the alkali-soluble resin is low, and after development, the storage stability of the composition is easily reduced and the viscosity increases. In order to further improve the developing performance and adhesion of the alkali-soluble polymer, the acid value of the alkali-soluble polymer is preferably 50-300 mgKOH / g, more preferably 50-250 mgKOH / g, even more preferably 70-250 mgKOH / g, and particularly preferably 100-250 mgKOH / g.

[0055] Furthermore, this application has discovered that the molecular weight distribution [weight-average molecular weight (Mw) / number-average molecular weight (Mn)] of the alkali-soluble resin also affects its developability. To improve developability, a molecular weight distribution of alkali-soluble resin of 1.5–6.0 is preferred, and particularly preferred to be 2.6–3.8. Simultaneously, a molecular weight distribution of 2.6–3.8 for the alkali-soluble resin results in a better match between the alkali-soluble resin and the aforementioned naphthylvinylpyridine compounds of this invention, further enhancing the aforementioned excellent properties of the naphthylvinylpyridine compounds, and providing a better synergistic effect, thus resulting in superior developability.

[0056] Preferably, the weight content of the alkali-soluble polymer in the photosensitive resin composition is 20-70%, more preferably 30-60%. When the content of the alkali-soluble polymer is 20% or more, the durability of the photosensitive resin composition for plating, etching, and other treatments can be improved. When the content is 70% or less, it is beneficial to improve the sensitivity of the photosensitive resin composition.

[0057] Compounds having olefinic unsaturated double bonds can promote film formation in photosensitive resin compositions. There are no particular limitations on the compounds having olefinic unsaturated double bonds; any photopolymerizable compound having at least one ethylene unsaturated bond within its molecule can be used. Preferably, compounds having olefinic unsaturated double bonds include, but are not limited to, compounds obtained by reacting α,β-unsaturated carboxylic acids with polyols, bisphenol A-type (meth)acrylate compounds, compounds obtained by reacting α,β-unsaturated carboxylic acids with compounds containing glycidyl groups, (meth)acrylate compounds with intramolecular urethane bonds, nonylphenoxypolyethyleneoxyacrylates, γ-chloro-β-hydroxypropyl-β'-(meth)acryloyloxyethyl-phthalate, β-hydroxyethyl-β'-(meth)acryloyloxyethyl-phthalate, β-hydroxypropyl-β'-(meth)acryloyloxyethyl-phthalate, phthalic acid compounds, and one or more of the group consisting of alkyl (meth)acrylates. Compared to other compounds with olefinic unsaturated double bonds, the above-mentioned compounds are advantageous for further improving the film-forming properties of photosensitive resins and reducing their costs.

[0058] In a preferred embodiment, the compound having an olefinic unsaturated double bond includes one or more compounds obtained by reacting α,β-unsaturated carboxylic acids with polyols, bisphenol A-type (meth)acrylate compounds, compounds obtained by reacting α,β-unsaturated carboxylic acids with compounds containing glycidyl groups, (meth)acrylate compounds with intramolecular urethane bonds, nonylphenoxypolyethyleneoxyacrylates, γ-chloro-β-hydroxypropyl-β'-(meth)acryloyloxyethyl-phthalate, β-hydroxyethyl-β'-(meth)acryloyloxyethyl-phthalate, β-hydroxypropyl-β'-(meth)acryloyloxyethyl-phthalate, phthalic acid compounds, and alkyl (meth)acrylates. More preferably, the compound having an olefinic unsaturated double bond is selected from any one or more of bisphenol A-type (meth)acrylate compounds and / or (meth)acrylate compounds with intramolecular urethane bonds.

[0059] More preferably, the aforementioned 2,2-bis{4-[(meth)acryloyloxypolyethoxy]phenyl}propane includes, but is not limited to, 2,2-bis{4-[(meth)acryloyloxydiethoxy]phenyl}propane, 2,2-bis{4-[(meth)acryloyloxytriethoxy]phenyl}propane, 2,2-bis{4-[(meth)acryloyloxytetraethoxy]phenyl}propane, 2,2-bis{4-[(meth)acryloyloxypentethoxy]phenyl}propane, 2,2-bis{4-[(meth)acryloyloxyhexaethoxy]phenyl}propane, 2,2-bis{4-[(meth)acryloyloxyheptaethoxy]phenyl}propane, 2,2-bis{4-[(meth)acryloyloxyoctaethoxy]phenyl}propane, 2, One or more of the group consisting of 2-bis{4-[(meth)acryloyloxynonethoxy]phenyl}propane, 2,2-bis{4-[(meth)acryloyloxydecaethoxy]phenyl}propane, 2,2-bis{4-[(meth)acryloyloxyundecaethoxy]phenyl}propane, 2,2-bis{4-[(meth)acryloyloxydodecethoxy]phenyl}propane, 2,2-bis{4-[(meth)acryloyloxydecaethoxy]phenyl}propane, 2,2-bis{4-[(meth)acryloyloxytetraethoxy]phenyl}propane, 2,2-bis{4-[(meth)acryloyloxydecaethoxy]phenyl}propane, and 2,2-bis{4-[(meth)acryloyloxydecaethoxy]phenyl}propane.

[0060] More preferably, the number of vinyl oxides per molecule of the above-mentioned 2,2-bis{4-[(meth)acryloyloxypolyethoxy]phenyl}propane is preferably 4-20, more preferably 8-15. These compounds can be used alone or in combination of two or more.

[0061] In a preferred embodiment, the above-mentioned (meth)acrylate compounds having an intramolecular urethane bond include, but are not limited to: addition reaction products of (meth)acrylate monomers having an OH group at the β-position and diisocyanate compounds, tris[(meth)acryloyloxytetraethylenediol isocyanate]hexamethylene isocyanurate, EO-modified urethane di(meth)acrylate, PO-modified urethane di(meth)acrylate, EO and PO-modified urethane di(meth)acrylate, etc. The diisocyanate compounds include, but are not limited to, one or more of the group consisting of isophorone diisocyanate, 2,6-toluene diisocyanate, 2,4-toluene diisocyanate, and 1,6-hexamethylene diisocyanate.

[0062] In a preferred embodiment, the above-mentioned nonylphenoxy polyethylene acrylate includes, but is not limited to, one or more of the following groups: nonylphenoxy tetraethylene acrylate, nonylphenoxy pentaethylene acrylate, nonylphenoxy hexaethylene acrylate, nonylphenoxy heptaethylene acrylate, nonylphenoxy octaethylene acrylate, nonylphenoxy nonaethylene acrylate, nonylphenoxy decaethylene acrylate, and nonylphenoxy undecaethylene acrylate.

[0063] In a preferred embodiment, the phthalic acid compounds mentioned above include, but are not limited to, one or more of the group consisting of γ-chloro-β-hydroxypropyl-β'-(meth)acryloyloxyethyl phthalate and β-hydroxyalkyl-β'-(meth)acryloyloxyalkyl phthalate.

[0064] In a preferred embodiment, the aforementioned alkyl methacrylates, but not limited to, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, tert-butyl methacrylate, 2-ethylhexyl methacrylate, phenyl methacrylate, isobornyl methacrylate, hydroxymethyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, and 2-ethylhexyl methacrylate, are mentioned. The methacrylate comprises one or more of the following groups: hydroxyethyl ester, 2-hydroxypropyl methacrylate, benzyl methacrylate, pentyl methacrylate, tetrahydrofurfuryl methacrylate, isooctyl methacrylate, ethoxylated nonylphenol methacrylate, propylene glycol polypropylene ether dimethacrylate, 1,9-nonanediol dimethacrylate, 1,10-decanediol dimethacrylate, ethoxylated polytetrahydrofurandiol dimethacrylate, and ethoxylated polypropylene glycol dimethacrylate. More preferably, the alkyl methacrylate comprises, but is not limited to, methyl methacrylate, ethyl methacrylate, trimethylolpropane trimethacrylate, ethoxylated trimethylolpropane trimethacrylate, pentaerythritol trimethacrylate, ethoxylated pentaerythritol tetramethacrylate, dipentaerythritol pentamethacrylate, and dipentaerythritol hexaacrylate.

[0065] From the perspective of improving resolution, plating resistance, and adhesion, in order to improve the resolution, plating resistance, and adhesion of photosensitive resin, preferably, the compound having olefinic unsaturated double bonds is selected from bisphenol A type (meth)acrylate compounds and / or (meth)acrylate compounds with intramolecular urethane bonds.

[0066] From the perspective of improving sensitivity and resolution, in order to improve the sensitivity and resolution of photosensitive resin, the compound having olefinic unsaturated double bonds is preferably a bisphenol A (meth)acrylate compound.

[0067] Commercially available bisphenol A (meth)acrylate compounds include, but are not limited to: 2,2-bis{4-[(meth)acryloyloxypolyethoxy]phenyl}propane (manufactured by Shin-Nakamura Chemical Industry Co., Ltd., BPE-200), 2,2-bis{4-[(meth)acryloyloxypolypropoxy]phenyl)propane (manufactured by Shin-Nakamura Chemical Industry Co., Ltd., BPE-5000; manufactured by Hitachi Chemical Co., Ltd., FA-321M), 2,2-bis{4-[(meth)acryloyloxypolybutoxy]phenyl}propane (manufactured by Shin-Nakamura Chemical Industry Co., Ltd., BPE-1300), etc.

[0068] In a preferred embodiment, the weight content of the compound having olefinic unsaturated double bonds in the photosensitive resin composition is 20-50%, more preferably 25-45%. When the content of the compound having olefinic unsaturated double bonds is 20% or more, the sensitivity and resolution of the photosensitive resin composition are further improved; when its content is below 50%, the photosensitive resin composition is easier to form into a thin film, and its durability for etching treatment is further improved.

[0069] In a preferred embodiment, component D comprises one or more of the following: imidazolium compounds, acridine compounds, aromatic ketone compounds, anthraquinone compounds, benzoin and benzoin alkyl ether compounds, oxime esters, triazine compounds, coumarin compounds, and thioxanthone compounds. More preferably, component D comprises one or more of the following: acridine compounds, aromatic ketone compounds, anthraquinone compounds, benzoin and benzoin alkyl ether compounds, oxime esters, triazine compounds, coumarin compounds, and thioxanthone compounds; more preferably, component D comprises one or more of the following: oxime esters, triazine compounds, and thioxanthone compounds.

[0070] Preferably, the diimidazole compounds include, but are not limited to: 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenyl-diimidazole, 2,2',5-tris(o-chlorophenyl)-4-(3,4-dimethoxyphenyl)-4',5'-diphenyl-1,1'-diimidazole, 2,2',5-tris(2-fluorophenyl)-4-(3,4-dimethoxyphenyl)-4',5'-diphenyl-diimidazole, 2,2'-di... (2,4-Dichlorophenyl)-4,4',5,5'-tetraphenyl-diimidazole, 2,2'-bis(2-fluorophenyl)-4-(o-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4',5'-diphenyl-diimidazole, 2,2'-bis(2-fluorophenyl)-4,4',5,5'-tetraphenyl-diimidazole, 2,2'-bis(2-methoxyphenyl)-4,4',5,5'-tetraphenyl-diimidazole, 2,2 '-Di(2-chloro-5-nitrophenyl)-4,4'-Di(3,4-dimethoxyphenyl)-5,5'-Di(o-chlorophenyl)-diimidazole, 2,2'-Di(2-chloro-5-nitrophenyl)-4-(3,4-dimethoxyphenyl)-5-(o-chlorophenyl)-4',5'-diphenyl-diimidazole, 2,2'-Di(2,4-dichlorophenyl)-4,4'-Di(3,4-dimethoxyphenyl)-5,5'- One or more of the following: bis(o-chlorophenyl)-diimidazole, 2-(2,4-dichlorophenyl)-4-(3,4-dimethoxyphenyl)-2',5-bis(o-chlorophenyl)-4',5'-diphenyl-diimidazole, 2-(2,4-dichlorophenyl)-2'-(o-chlorophenyl)-4,4',5,5'-tetraphenyl-diimidazole, and 2,2'-bis(2,4-dichlorophenyl)-4,4',5,5'-tetraphenyl-diimidazole.

[0071] Preferably, the acridine compounds include, but are not limited to, one or more of the following: 9-phenylacridine, 9-p-methylphenylacridine, 9-m-methylphenylacridine, 9-o-chlorophenylacridine, 9-o-fluorophenylacridine, 1,7-di(9-acridyl)heptane, 9-ethylacridine, 9-(4-bromophenyl)acridine, 9-(3-chlorophenyl)acridine, 1,7-bis(9-acridyl)heptane, 1,5-bis(9-acridylpentane), and 1,3-bis(9-acridyl)propane.

[0072] Preferably, the aromatic ketone compounds include, but are not limited to: acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, benzophenone, 4-benzoyl diphenyl sulfide, 4-benzoyl-4'-methyl diphenyl sulfide, 4-benzoyl-4'-ethyl diphenyl sulfide, 4-benzoyl-4'-propyl diphenyl sulfide, and 4,4'-bis(diethylamino) Benzophenone, 4-p-Toluylmercaptobenzophenone, 2,4,6-Trimethylbenzophenone, 4-Methylbenzophenone, 4,4'-Bis(dimethylamino)benzophenone, 4,4'-Bis(methyl, ethylamino)benzophenone, acetophenone dimethyl ketal, benzoylayl dimethyl ketal, α,α'-Dimethylbenzoylayl ketal, α,α'-Diethoxyacetophenone, 2-Hydroxy-2-methyl-1-phenylpropanone, 1-Hydroxycyclohexylbenzophenone Ketones, 2-hydroxy-2-methyl-1-p-hydroxyethyl ether phenylacetone, 2-methyl-1-(4-methylmercaptophenyl)-2-morpholine-1-propanone, 2-benzyl-2-dimethylamino-1-(4-morpholinephenyl)-1-butanone, phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, 2,4,6-(trimethylbenzoyl)diphenylphosphine oxide, 2-hydroxy-1-{3-[4-(2-hydroxy-2-methyl-propionyl)} One or more of the following: [-phenyl]-1,1,3-trimethyl-indene-5-yl}-2-methylpropionanone, 2-hydroxy-1-{1-[4-(2-hydroxy-2-methyl-propionyl)-phenyl]-1,3,3-trimethyl-indene-5-yl}-2-methylpropionanone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylprop-1-one, and 4-(2-hydroxyethoxy)-phenyl-(2-hydroxy-2-propyl)one.

[0073] Preferably, the anthraquinone compounds include, but are not limited to, one or more of the following: 2-phenylanthraquinone, 2,3-diphenylanthraquinone, 1-chloroanthraquinone, 2-methylanthraquinone, 2,3-dimethylanthraquinone, 2-ethylanthraquinone-9,10-diethyl ester, 1,2,3-trimethylanthraquinone-9,10-dioctyl ester, 2-ethylanthraquinone-9,10-di(4-chlorobutyrate methyl ester), 2-{3-[(3-ethyloxetane-3-yl)methoxy]-3-oxopropyl}anthracene-9,10-diethyl ester, 9,10-dibutoxyanthracene, 9,10-diethoxy-2-ethylanthracene, 9,10-di(3-chloropropoxy)anthracene, 9,10-di(2-hydroxyethimeryl)anthracene, and 9,10-di(3-hydroxy-1-propimeryl)anthracene.

[0074] Preferably, benzoin and benzoin alkyl ether compounds include, but are not limited to, one or more of benzoin methyl ether, benzoin ethyl ether, and benzoin phenyl ether.

[0075] Preferably, the oxime esters include, but are not limited to: 1-(4-phenylthiophenyl)-n-octane-1,2-dione-2-benzoic acid oxime ester, 1-[6-(2-methylbenzoyl)-9-ethylcarbazole-3-yl]-ethane-1-one-acetate oxime ester, 1-[6-(2-methylbenzoyl)-9-ethylcarbazole-3-yl]-butane-1-one-acetate oxime ester, 1-[6-(2-methylbenzoyl)-9-ethylcarbazole-3-yl]-propane-1-one-acetate oxime ester, 1-[6-(2-methylbenzoyl)-9-ethylcarbazole-3-yl]-1-cyclohexyl-methane-1-one-acetate oxime ester, 1-[6-(2-methylbenzoyl)-9-ethylcarbazole-3-yl]-(3-cyclohexyl)methane-1-one-acetate oxime ester, and 1-[6-(2-methylbenzoyl)-9-ethylcarbazole-3-yl]-(3-cyclohexyl)methane-1-one-acetate oxime ester. 1-(4-phenylthiophenyl)-(3-cyclopentyl)-propane-1,2-dione-2-benzoic acid oxime ester, 1-(4-phenylthiophenyl)-(3-cyclohexyl)-propane-1,2-dione-2-cyclohexylcarboxylic acid oxime ester, 1-[6-(2-methylbenzoyl)-9-ethylcarbazole-3-yl]-( 3-Cyclopentyl)-propane-1,2-dione-2-acetate oxime ester, 1-(6-o-methylbenzoyl-9-ethylcarbazole-3-yl)-(3-cyclopentyl)-propane-1,2-dione-2-benzoate oxime ester, 1-(4-benzoyldiphenyl sulfide)-(3-cyclopentylacetone)-1-oxime acetate ester, 1-(6-o-methylbenzoyl-9-ethyl Carbazole-3-yl)-(3-cyclopentylacetone)-1-oxime cyclohexylcarboxylate, 1-(4-benzoyldiphenyl sulfide)-3-cyclopentylacetone)-1-oxime cyclohexylcarboxylate, 1-(6-o-methylbenzoyl-9-ethylcarbazole-3-yl)-(3-cyclopentyl)-propane-1,2-dione-2-o-methylbenzoate oxime, 1-(4-phenylthio) 1-(3-cyclopentyl)-propane-1,2-dione-2-cyclohexylcarboxylate oxime ester, 1-(4-thienylcarboxyl-diphenyl sulfide-4'-yl)-3-cyclopentyl-propane-1-one-acetate oxime ester, 1-(4-benzoyldiphenyl sulfide)-(3-cyclopentyl)-propane-1,2-dione-2-oxime acetate ester, 1-(6-nitro-9- Ethylcarbazole-3-yl)-3-cyclohexyl-propane-1-one-acetate oxime ester, 1-(6-o-methylbenzoyl-9-ethylcarbazole-3-yl)-3-cyclohexyl-propane-1-one-acetate oxime ester, 1-(6-thienylcarbamoyl-9-ethylcarbazole-3-yl)-(3-cyclohexylacetone)-1-oxime acetate ester, 1-(6-furanoyl- 9-Ethylcarbazole-3-yl)-(3-cyclopentylacetone)-1-oxime acetate, 1,4-diphenylpropane-1,3-dione-2-acetate oxime, 1-(6-furfuryl-9-ethylcarbazole-3-yl)-(3-cyclohexyl)-propane-1,2-dione-2-acetate oxime, 1-(4-phenylthiophenyl)-(3-cyclohexyl)-propane-1,2-Diketone-2-acetate oxime ester, 1-(6-furanoyl-9-ethylcarbazole-3-yl)-(3-cyclohexylacetone)-1-oxime oxime ester, 1-(4-phenylthiophenyl)-(3-cyclohexyl)-propane-1,2-dione-3-benzoic acid oxime ester, 1-(6-thienyl-9-ethylcarbazole-3-yl)-(3-cyclohexyl)-propane-1,2-dione-2-acetate oxime ester, 2-[(benzoyloxy)imino] 1-Phenylacetane-1-one, 1-Phenylacetane-1,2-propanedione-2-(oxoacetyl)oxime, 1-(4-phenylthiophenyl)-2-(2-methylphenyl)-ethane-1,2-dione-2-acetic acid oxime ester, 1-(9,9-dibutyl-7-nitrofluoren-2-yl)-3-cyclohexyl-propane-1-one-acetic acid oxime ester, 1-{4-[4-(thiophene-2-formyl)phenylthio]phenyl}-3-cyclopentylpropane-1, 2-Diketone-2-acetate oxime ester, 1-[9,9-dibutyl-2-yl]-3-cyclohexylpropylpropane-1,2-diketone-2-acetate oxime ester, 1-[6-(2-benzoyloxyimino)-3-cyclohexylpropyl-9-ethylcarbazole-3-yl]octane-1,2-diketone-2-benzoate oxime ester, 1-(7-nitro-9,9-diallylfluoren-2-yl)-1-(2-methylphenyl)methyl ketone-acetate oxime ester, 1-[6- One or more of the following: (2-methylbenzoyl)-9-ethylcarbazole-3-yl]-3-cyclopentylpropane-1-one-benzoic acid oxime ester, 1-[7-(2-methylbenzoyl)-9,9-dibutylfluoren-2-yl]-3-cyclohexylpropane-1,2-dione-2-acetic acid oxime ester, and 1-[6-(furan-2-formyl)-9-ethylcarbazole-3-yl]-3-cyclohexylpropane-1,2-dione-2-ethoxyformyl oxime ester.

[0076] Preferably, the triazine compounds include, but are not limited to: 2-(4-ethylbiphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-(3,4-methyleneoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine, 3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid, 1,1,1,3,3,3-hexafluoroisopropyl-3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid ester, ethyl-2-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}acetate, 2-ethoxyethyl-2-{4-[2,4-bis(trichloromethyl)- The following are one or more of the following: s-triazin-6-yl]phenylthio}acetate, cyclohexyl-2-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}acetate, benzyl-2-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}acetate, 3-{chloro-4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid, 2,4-bis(trichloromethyl)-6-p-methoxystyryl-s-triazine, 2,4-bis(trichloromethyl)-6-(1-p-dimethylaminophenyl)-1,3-butadienyl-s-triazine, and 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine.

[0077] Preferably, the coumarin compounds are, but are not limited to, one or more of the following: 3,3'-carbonylbis(7-diethylaminecoumarin), 3-benzoyl-7-diethylaminecoumarin, 3,3'-carbonylbis(7-methoxycoumarin), 7-diethylamino-4-methylcoumarin, 3-(2-benzothiazole)-7-(diethylamino)coumarin, 7-(diethylamino)-4-methyl-2H-1-benzopyran-2-one [7-(diethylamino)-4-methylcoumarin], and 3-benzoyl-7-methoxycoumarin.

[0078] Preferably, the thioxanthone compounds include, but are not limited to, one or more of the following: thioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propoxythioxanthone, isopropylthioxanthone, and diisopropylthioxanthone.

[0079] To improve the photoinitiating properties of the photosensitive resin composition, the weight content of component D in the photosensitive resin composition is preferably 0.01 to 10%. More preferably, it is 1 to 5%.

[0080] To improve the application performance of the above-mentioned naphthylvinylpyridine compounds in the composition, thereby further enhancing the photoinitiating performance of the photosensitive resin composition, in a more preferred embodiment, component D includes one or more of a diimidazole compound, an oxime ester compound, a triazine compound, or a thioxanone compound. For example, component D includes a diimidazole compound and an oxime ester compound, with a weight ratio of the imidazole compound to the oxime ester compound of (1-5):1; component D includes a diimidazole compound and a triazine compound, with a weight ratio of the diimidazole compound to the triazine compound of (1-5):1; component D includes a diimidazole compound and a thioxanone compound, with a weight ratio of the diimidazole compound to the thioxanone compound of (1-5):1.

[0081] In an optional embodiment, in addition to the components described above, the photosensitive resin composition of the present invention may optionally include one or more of hydrogen donors, dyes, pigments, photochromic agents, fillers, plasticizers, stabilizers, coating aids, and release accelerators.

[0082] In the above-mentioned photosensitive resin composition, there is no particular limitation on the specific type of hydrogen donor. Preferably, the hydrogen donor includes, but is not limited to, one or more of the following: amine compounds, carboxylic acid compounds, organosulfur compounds containing thiol groups, or alcohol compounds. Optionally, the hydrogen donor includes, but is not limited to, triethanolamine, methyl 4-dimethylaminobenzoate, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, phenyl thioacetic acid, methyl phenyl thioacetic acid, ethyl phenyl thioacetic acid, dimethoxyphenyl thioacetic acid, chlorophenyl thioacetic acid, dichlorophenyl thioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthioacetic acid, N-naphthylglycine, naphthoxyacetic acid, 2-mercaptobenzothiazole (MBO), 2-mercaptobenzimidazole (MBI), dodecyl mercaptan, ethylene glycol bis(3-mercaptobutyrate), etc.

[0083] In a preferred embodiment, the dyes, pigments, and photochromic agents include, but are not limited to: tris(4-dimethylaminophenyl)methane (i.e., leuco crystal violet, LCV), tris(4-dimethylamino-2-methylphenyl)methane, fluorane dyes, toluenesulfonic acid monohydrate, basic fuchsin, phthalocyanine dyes (such as phthalocyanine green and / or phthalocyanine blue), auramine base, para fuchsin, crystal violet, methyl orange, Nile blue 2B, Victoria blue, peacock green, adamantine green, basic blue 20, brilliant green, eosin, ethyl violet, sodium erythrosine B, methyl green, phenolphthalein, alizarin red S, thymolphthalein phthaloyl, methyl violet 2B, quinaldin red, and rose red. Sodium agar, Mitanil Yellow, Thymol Sulfophthalide, Xylenol Blue, Methyl Orange, Orange IV, Diphenyllucarbazone, 2,7-Dichlorofluorescein, Panmethyl Red, Congo Red, Benzopure Red 4B, α-Naphthyl Red, Phenacetin, Methyl Violet, Victoria Pure Blue BOH, Rhodamine 6G, Diphenylamine, Dibenzylaniline, Triphenylamine, N,N-Diethylaniline, Di-p-diamine, p-Toluidine, Benzotriazole, Methylphentriazole, 4,4'-Didiamine, o-Chloroaniline, White Crystal Violet, White Malachite Green, White Aniline, White Methyl Violet, Azo dyes, and titanium dioxide are among one or more of these.

[0084] In a preferred embodiment, the filler includes, but is not limited to, one or more of the following: silica, alumina, talc, calcium carbonate, barium sulfate, etc.

[0085] In a preferred embodiment, the plasticizer includes, but is not limited to: phthalates (such as dibutyl phthalate, diheptyl phthalate, dioctyl phthalate, diallyl phthalate), sulfonamides (such as triethylene glycol diacetate, tetraethylene glycol diacetate, etc., p-toluenesulfonamide, benzenesulfonamide, n-butylbenzenesulfonamide), and phosphate esters (such as triphenyl phosphate, trimethyl phosphate, triethyl phosphate, triphenyl phosphate, trimethylbenzene phosphate, trimethylbenzene phosphate, etc.). Tolyl phosphate, tolyl diphenyl phosphate, tris(dimethyl) phosphate, 2-naphthyl diphenyl phosphate, tolyl di-2,6-dimethyl phosphate, aromatic condensed phosphate, tris(chloropropyl) phosphate, tris(tribromoneopentyl) phosphate, halogenated condensed phosphate), alcohol esters (such as triethylene glycol dioctanoate, triethylene glycol di(2-ethylhexanoate), tetraethylene glycol diheptanoate), diethyl sebacate, dibutyl sebacate, tri(2-ethylethyl) phosphate, Brij30 (C 12 H 25 (OCH2CH2)4OH), and Brij35 (C 12 H 25 (OCH2CH2) 20 One or more of the following: OH)

[0086] In a preferred embodiment, the stabilizer includes, but is not limited to, one or more of the following: hydroquinone, 1,4,4-trimethyl-diazobicyclo(3.2.2)-non-2-ene-2,3-dioxide, 1-phenyl-3-pyrazolone, p-methoxyphenol, alkyl and aryl-substituted hydroquinones and quinones, tert-butylcatechol, 1,2,3-phenylpyrogallol, copper resin, naphthylamine, β-naphthol, cuprous chloride, 2,6-di-tert-butyl-p-cresol, phenothiazine, pyridine, nitrobenzene, dinitrobenzene, p-toluenequinone, and chloroquinone.

[0087] In a preferred embodiment, the coating aid includes, but is not limited to, one or more of the following: acetone, methanol, methyl alcohol, ethyl alcohol, isopropyl alcohol, methyl ethyl ketone, propylene glycol monomethyl ether acetate, ethyl lactate, cyclohexanone, γ-butyrolactone, dichloromethane, etc.

[0088] In a preferred embodiment, the stripping accelerator includes (but is not limited to): one or more of benzenesulfonic acid, toluenesulfonic acid, xylenesulfonic acid, phenolsulfonic acid, methyl, propyl, heptyl, octyl, decyl, dodecyl, and other alkylbenzenesulfonic acids.

[0089] To ensure that the additives are fully utilized, it is preferable that the weight content of the additives in the photosensitive resin composition is 1 to 10%.

[0090] To further balance the excellent properties of each component in the photosensitive resin composition, thereby improving the overall photosensitivity, resolution, and adhesion of the composition, in a preferred embodiment, the photosensitive resin composition comprises, by weight parts, 0.1 to 0.3 parts of a naphthylvinylpyridine compound, 40 to 50 parts of an acrylic copolymer of methyl methacrylate / methacrylic acid / n-butyl acrylate (mass ratio 70 to 75: 20 to 25: 10 to 15), 15 to 25 parts of an acrylic copolymer of methyl methacrylate / methacrylic acid / n-butyl acrylate (mass ratio 50 to 55: 30 to 35: 20 to 25), and 10 to 20 parts of... The following are components: a ureaalkylation of hexamethylene diisocyanate and pentapropylene glycol monomethacrylate; 5-15 parts of dipentaerythritol hexaacrylate; 1-10 parts of tetra-nonylphenyl heptaethylene glycol dipropylene glycol acrylate; 1-10 parts of a triacrylate of p-trimethylolpropane with an average of 3 moles of cyclohexane; 1-3 parts of BCIM; 0.1-1 part of 1-[9,9-dibutyl-2-yl]-3-cyclohexylpropylpropane-1,2-dione-2-acetate oxime ester (or 2,4-bis(trichloromethyl)-6-(1-p-dimethylaminophenyl)-1,3-butadienyl-s-triazine, or diisopropylthioxanthone); 0.01-0.0 The composition includes 5 parts malachite green, 0.1–0.2 parts leuco crystal violet, 0.1–0.2 parts 5-carboxy-1,2,3-benzotriazole, 0.05–0.15 parts 2,6-di-tert-butyl-p-cresol, 0.1–0.2 parts N-phenylglycine, 20–40 parts E6, and 0.1–0.3 parts 2-(4-ethylbiphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine. The naphthylvinylpyridine compound may have the following structure:

[0091]

[0092] In another typical embodiment of this application, a patterning method is provided, which includes: patterning a photosensitive resin composition to obtain a mask, wherein the photosensitive resin composition is the above-mentioned photosensitive resin composition.

[0093] Since the photosensitive resin composition of this application has good photosensitivity, resolution and adhesion, when applied to the patterning process, the resulting pattern also has good photosensitivity, resolution and adhesion.

[0094] In practical applications, this graphical method is used for patterning processes in the manufacture of printed circuit boards, protective patterns, conductor patterns, lead frames, or semiconductor packages.

[0095] The following examples illustrate the application of graphical methods.

[0096] The photosensitive resin composition of the present invention can be prepared into a dry film, i.e. a photosensitive resin laminate, and applied in the manufacture of printed circuit boards, protective patterns, conductor patterns, lead frames, and semiconductor packages, forming the desired patterns on different substrates through different processes.

[0097] The dry film of the present invention, namely a photosensitive resin laminate, comprises: a photosensitive resin layer formed by a photosensitive resin composition and a support supporting the photosensitive resin layer.

[0098] Typically, the preparation of a dry film includes: coating a photosensitive resin composition onto a support and drying it to form a photosensitive resin layer; optionally, applying a cover film (protective layer) as needed. Preferably, the drying conditions are drying at 60-100°C for 0.5-15 min. The thickness of the photosensitive resin layer is preferably 5-95 μm, more preferably 10-50 μm, and even more preferably 15-30 μm. If the thickness of the photosensitive resin layer is less than 5 μm, the insulation performance is poor, while if the thickness of the photosensitive resin layer exceeds 95 μm, the resolution may be poor.

[0099] Specific examples of the support can be various types of plastic films, such as polyethylene terephthalate, polyvinyl naphthalate, polypropylene, polyethylene, cellulose acetate, polymethyl methacrylate, methacrylate copolymer, polyvinyl chloride, polyvinyl alcohol, polycarbonate, polystyrene, cellophane, vinyl chloride copolymer, polyamide, polyimide, ethylene-vinyl chloride copolymer, polytetrafluoroethylene, polytrifluoroethylene, and similar materials. Furthermore, composite materials composed of two or more materials can also be used. Preferably, polyethylene terephthalate, which has excellent light transmittance, is used. The thickness of the support is preferably 5–150 μm, more preferably 10–50 μm.

[0100] There are no special restrictions on the coating of photosensitive resin compositions. Conventional methods such as spraying, roller coating, rotary coating, slot coating, compression coating, curtain coating, dye coating, line coating, doctor blade coating, roller coating, squeegee coating, spraying, and dip coating can be used.

[0101] In one embodiment, the application of the above-described dry film in the manufacture of printed circuit boards is provided, including:

[0102] (1) Lamination process: The photosensitive resin laminate is laminated onto a copper-clad laminate or a flexible substrate;

[0103] (2) Exposure process: Expose the photosensitive resin layer in the photosensitive resin laminate to the active light in an image-like manner to cure the exposed part.

[0104] (3) Development process: The unexposed parts of the photosensitive resin layer are removed with a developing solution to form a protective pattern;

[0105] (4) Conductor pattern formation process: Etching or plating the parts of the copper-clad laminate or flexible substrate surface that are not covered by the protective pattern;

[0106] (5) Peeling process: Peel the protective pattern from the copper-clad laminate or flexible substrate.

[0107] In another embodiment, the application of the above-mentioned dry film in the manufacture of protective patterns is provided, including the lamination process, exposure process and development process as described above, the difference being that: in the lamination process, the photosensitive resin laminate can be laminated on substrates of various materials.

[0108] In another embodiment, the application of the above-mentioned dry film in the manufacture of conductor patterns is provided, including the above-mentioned lamination process, exposure process, development process and conductor pattern formation process, the difference being that: in the lamination process, the photosensitive resin laminate is laminated on a metal plate or a metal-coated insulating plate.

[0109] In another embodiment, the application of the above-mentioned dry film in the manufacture of lead frame lines is provided, including the above-mentioned lamination process, exposure process, development process, and conductor pattern formation process, the difference being that: in the lamination process, the photosensitive resin laminate is laminated on the metal plate, and in the conductor pattern formation process, the portion not covered by the protected pattern is etched.

[0110] In another embodiment, the application of the above-mentioned dry film in the manufacture of semiconductor packaging is provided, including the above-mentioned lamination process, exposure process, development process, and conductor patterning process, the difference being that: in the lamination process, the photosensitive resin laminate is laminated on a wafer having a large-scale integrated circuit, and in the conductor patterning process, the portion not covered by the protected pattern is plated.

[0111] The photosensitive resin composition of the present invention can also be directly coated onto the corresponding substrates in each corresponding manufacturing step by a wet film coating machine, that is, it is used as a wet film in the manufacturing of printed circuit boards, protective patterns, conductor patterns, lead frames, and semiconductor packages, and the desired patterns are formed on different substrates through different processes.

[0112] That is, the photosensitive resin composition of the present invention can be directly coated onto a substrate by wet film application for use in the manufacture of printed circuit boards, protective patterns, conductor patterns, lead frames, semiconductor packages, etc.

[0113] Non-limitingly, the photosensitive resin composition can be coated onto the substrate using conventional methods such as roller coating, blade coating, spray coating, and dip coating, and then dried to form a photosensitive resin layer.

[0114] After the photosensitive resin layer is formed on the substrate, subsequent processes such as exposure, development, conductor pattern formation, and stripping can be performed in the same manner as dry film applications.

[0115] In the exposure process, exposure can be achieved through methods such as mask exposure (where a negative or positive mask pattern of a wiring diagram illuminates the active light source in an image-like manner), projection exposure, or direct tracing exposure methods such as laser direct imaging exposure or digital optical processing exposure to illuminate the active light source in an image-like manner. As the light source for the active light, known light sources can be used, such as gas lasers (e.g., carbon arc lamps, mercury vapor arc lamps, ultra-high pressure lamps, high pressure lamps, xenon lamps, argon lasers), solid-state lasers (e.g., YAG lasers), semiconductor lasers, and gallium nitride-based blue-violet lasers, which effectively emit ultraviolet light. Additionally, light sources that effectively emit visible light, such as photographic floodlights and fluorescent lamps, can also be used. The photosensitive resin composition of the present invention does not particularly limit the type of light source for the active light, and the exposure amount is preferably 10–1000 mJ / cm². 2 .

[0116] In the developing process, the unexposed portions of the photosensitive resin layer are removed using a developing solution. If a support is present on the photosensitive resin layer, the support can be removed first using an automatic stripper, and then the unexposed portions can be removed using a developing solution such as an alkaline aqueous solution, an aqueous developing solution, or an organic solvent. Examples of alkaline aqueous solutions include 0.1–5% by mass sodium carbonate solution, 0.1–5% by mass potassium carbonate solution, and 0.1–5% by mass sodium hydroxide solution, with a preferred pH value of 9–11. Surfactants, defoamers, and organic solvents can also be added to the alkaline aqueous solution. The developing method can be conventional methods such as immersion, spraying, or brushing.

[0117] In the etching process, a resist pattern (i.e., a protective pattern) formed on a substrate is used as a mask to etch away the uncovered conductive layer of the substrate used for circuit formation, thereby forming a conductive pattern. The etching method can be selected depending on the conductive layer to be removed. Examples of etching solutions include copper oxide solutions, iron oxide solutions, alkaline etching solutions, and hydrogen peroxide-based etching solutions.

[0118] In the plating process, using a resist pattern formed on a substrate as a mask, copper and solder are plated onto the insulating plate of the circuit forming substrate that is not covered. After the plating process, the resist pattern is removed to form a conductor pattern. The plating process can be either electroplating or electroless plating, with electroless plating being preferred. Examples of electroless plating include: copper plating such as copper sulfate plating and copper pyrophosphate plating; soldering such as high-throw solder plating; nickel plating such as watt bath (nickel sulfate-nickel chloride) plating and nickel sulfamate plating; and gold plating such as hard gold plating and soft gold plating.

[0119] The resist pattern can be removed by using an aqueous solution that is more alkaline than the alkaline aqueous solution used in the developing process. An example of a strongly alkaline aqueous solution is a 1-10% by mass sodium hydroxide aqueous solution.

[0120] The present application will be further described in detail below with reference to specific embodiments, which should not be construed as limiting the scope of protection claimed in the present application.

[0121] 1. Preparation of Naphthylvinylpyridine compounds

[0122] 1.1 Preparation of product C1

[0123]

[0124] In a 2000 mL four-necked flask, 100.0 g of 1-naphthaldehyde, 500.0 g of acetic acid, and 133.3 g of ammonium acetate were added sequentially, and stirring was started. The internal temperature was raised to 100 °C, and 41.5 g of cyclopentanone was added dropwise over 30 min. The reaction was continued for 6 h. The reaction process was monitored by HPLC, and the reaction was stopped when the remaining 1-naphthaldehyde was ≤1%. After cooling to room temperature, the mixture was filtered. The crude product was slurried with 300 g of methanol at 50 °C for 1 h, filtered, and dried to obtain 77.9 g of product C1 with a purity of 99.15%.

[0125] The structure of product C1 was confirmed using LCMS. Mass spectrometry analysis, aided by the instrument's software, yielded molecular fragment peaks at 563 and 564. The molecular weight of the product was 562, consistent with T+1 and T+2 values. NMR further confirmed the structure of product C1, with the following data: 1 H NMR(400MHz,DMSO-d6)9.03(d,2H),8.29(d,1H),8.15(d,1H),8.13(d,2H),8. 02-7.75(m,9H),7.71-7.45(m,8H),2.90-2.86(m,4H),2.31-2.26(m,4H)ppm.

[0126] 1.2 Preparation of product C2

[0127]

[0128] Following the synthesis method of product C1, the raw material a, i.e., 1-naphthaldehyde, was replaced with 2-methoxy-1-naphthaldehyde to obtain product C2 with a purity of 99.04%.

[0129] The structure of product C2 was confirmed using LCMS. Mass spectrometry analysis, aided by the instrument's software, yielded molecular fragment peaks at 653 and 654, indicating a molecular weight of 652, consistent with T+1 and T+2. NMR further confirmed the structure of product C2, with the following data: 1 H NMR(400MHz,DMSO-d6)9.03(d,2H),8.42(d,2H),8.03(d,2H),7.90-7.79(m,6H),7.79(d,2H),7.49-7.3 8(m,4H),7.25(d,1H),6.99(d,1H),3.94(s,6H),3.80(s,3H),2.90-2.83(m,4H),2.32-2.29(m,4H)ppm.

[0130] 1.3 Preparation of product C3

[0131]

[0132] Following the synthesis method of product C1, the raw material a, i.e., 1-naphthaldehyde, was replaced with 2,6-dimethoxy-1-naphthaldehyde to obtain product C3 with a purity of 99.05%.

[0133] The structure of product C3 was confirmed using LCMS. Mass spectrometry analysis, aided by the instrument's software, yielded molecular fragment peaks at 743 and 744. The molecular weight of the product was 742, consistent with T+1 and T+2 values. NMR further confirmed the structure of product C3, with the following data: 1 H NMR(400MHz,DMSO-d6)8.46(d,2H),8.01(d,1H),7.79-7.75(m,5H),7.23(s,3H),7.10(d,1 H),6.92-6.86(m,5H),3.93(s,6H),3.82(s,12H),2.93-2.83(m,4H),2.31-2.25(m,4H)ppm.

[0134] 1.4 Preparation of product C4

[0135]

[0136] Following the synthesis method of product C1, the raw material a, i.e., 1-naphthaldehyde, was replaced with 4-isopropyl-1-naphthaldehyde to obtain product C4 with a purity of 99.13%.

[0137] The structure of product C4 was confirmed using LCMS. Mass spectrometry analysis, aided by the instrument's software, yielded molecular fragment peaks at 689 and 690, indicating a molecular weight of 688, consistent with T+1 and T+2 values. NMR further confirmed the structure of product C4, with the following data: 1H NMR(400MHz,DMSO-d6)9.03(d,1H),8.13-8.06(m,6H),7.91(d,2H),7.85(d,2H),7.72(t,2H),7.59(t,1 H),7.35(t,3H),7.19(d,1H),6.96(d,2H),2.89-2.84(m,7H),2.31-2.28(m,4H),1.33-1.28(m,18H)ppm.

[0138] 1.5 Preparation of product C5

[0139]

[0140] Following the synthesis method of product C1, raw material a, i.e., 1-naphthoaldehyde, was replaced with 2-naphthoaldehyde, and raw material b, i.e., cyclopentanone, was replaced with cyclohexanone, to obtain product C5 with a purity of 99.27%.

[0141] The structure of product C5 was confirmed using LCMS. Mass spectrometry analysis, using the instrument's accompanying software, yielded molecular fragment peaks at 591 and 592. The molecular weight of the product was 590, consistent with T+1 and T+2. NMR further confirmed the structure of product C5, with the following data: 1 H NMR(400MHz, DMSO-d6)8.24(m,3H),8.10-8.03(m,6H),7.91-7.88(m,6H),7.80-7.76(m,2H),7.65-7.59(m,6H),3.15(m,4H),1.96-1.89(m,8H)ppm.

[0142] 1.6 Preparation of product C6

[0143]

[0144] Following the synthesis method of product C1, the raw material a, i.e., 1-naphthaldehyde, was replaced with 4-dimethylamino-1-naphthaldehyde to obtain product C6 with a purity of 99.17%.

[0145] The structure of product C6 was confirmed using LCMS. Mass spectrometry analysis, using the instrument's accompanying software, yielded molecular fragment peaks at 692 and 693, indicating a molecular weight of 691, consistent with T+1 and T+2 values. The structure of product C8 was further confirmed using NMR, with the following data:

[0146] 1H NMR(400MHz,DMSO-d6)9.00(d,1H),8.52(d,3H),8.13(s,2H),7.97(d,1H),7.85(d,2H),7.77(d,2 H),7.68(d,2H),7.56(t,2H),7.44(t,3H),7.29(d,2H),2.89-2.86(m,22H),2.31-2.28(m,4H)ppm.

[0147] 1.7 Preparation of product C7

[0148]

[0149] Following the synthesis method of product C1, the raw material a, i.e., 1-naphthoaldehyde, was replaced with methyl 4-formyl-1-naphthoic acid to obtain product C7 with a purity of 99.17%.

[0150] The structure of product C7 was confirmed using LCMS. Mass spectrometry analysis, using the instrument's accompanying software, yielded molecular fragment peaks at 737 and 738. The molecular weight of the product was 736, consistent with T+1 and T+2. NMR further confirmed the structure of product C7, with the following data: 9.00 (d, 3H), 8.92 (d, 1H), 8.70 (d, 1H), 8.46 (d, 2H), 8.13 (s, 2H), 8.02 (d, 1H), 7.86–7.82 (m, 7H), 7.69–7.52 (m, 3H), 3.90 (s, 9H), 2.89–2.86 (m, 4H), 2.31–2.28 (m, 4H) ppm.

[0151] 1.8 Preparation of product C8

[0152]

[0153] Following the synthesis method of product C1, the raw material a, i.e., 1-naphthaldehyde, was replaced with 2,6-dimethoxy-1-naphthaldehyde to obtain product C8 with a purity of 99.17%.

[0154] The structure of product C8 was confirmed using LCMS. Mass spectrometry analysis, using the instrument's accompanying software, yielded molecular fragment peaks at 771 and 772. The molecular weight of the product was 770, consistent with T+1 and T+2. NMR further confirmed the structure of product C8, with the following data: 1H NMR(400MHz,DMSO-d6)8.40(s,2H),7.97(d,1H),7.76-7.72(m,5H),7.20(s,3H),7.09(d,1 H),6.89-6.84(m,5H),3.90(s,6H),3.81(s,12H),3.15-3.12(m,4H),1.94-1.87(m,8H)ppm.

[0155] 1.9 Preparation of product C9

[0156]

[0157] Following the synthesis method of product C1, the raw material a, i.e., 1-naphthaldehyde, was replaced with 2-bromo-1-naphthaldehyde to obtain product C9 with a purity of 99.18%.

[0158] The structure of product C9 was confirmed using LCMS. Mass spectrometry analysis, aided by the instrument's software, yielded molecular fragment peaks at 827 and 828. The molecular weight of the product was 826, consistent with T+1 and T+2 values. NMR further confirmed the structure of product C9, with the following data:

[0159] 1 H NMR(400MHz,DMSO-d6)8.99(d,1H),8.42(s,2H),8.29(d,1H),8.27-8.05(m,1 2H),7.57(t,1H),7.40-7.33(m,3H),3.18-3.12(m,4H),1.94-1.79(m,8H)ppm.

[0160] 2. Preparation of photosensitive resin composition

[0161] Referring to the formulation shown in Table 1, the components were mixed evenly to obtain the photosensitive resin composition. Unless otherwise specified, all parts shown in Table 1 are parts by weight.

[0162] Table 1

[0163]

[0164]

[0165] Note: E6 is the solvent.

[0166] The meanings of the component codes in Table 1 are shown in Table 2 below.

[0167] Table 2

[0168]

[0169]

[0170] 3 Performance Evaluation

[0171] 3.1 Evaluation Method

[0172] <Dry film preparation>

[0173] The photosensitive resin composition was thoroughly stirred and uniformly coated onto the surface of a 25 μm thick polyethylene terephthalate film as a support using a rod coater. The film was then dried at 95°C for 5 minutes in a dryer to form a 40 μm thick photosensitive resin layer. A 15 μm thick polyethylene film was then laminated onto the surface of the unlaminated polyethylene terephthalate film as a protective layer to obtain a dry film.

[0174] <Substrate Surface Leveling>

[0175] As a substrate, a 1.2 mm thick copper-clad laminate with 35 μm thick rolled copper foil was used, and the surface was wet polished with a polishing roller [Scotch-Brite (registered trademark) HD#600 manufactured by 3M, twice].

[0176] Lamination

[0177] The polyethylene film protective layer is peeled off from the dry film and then laminated onto a copper-clad laminate preheated to 60°C using a hot roller laminator (Asahi Kasei AL-70) at a roller temperature of 105°C. The gas pressure is 0.35 MPa and the lamination speed is 1.5 m / min.

[0178] <Exposure>

[0179] The mask was placed on a polyethylene terephthalate film serving as a support, and then heated by an ultra-high pressure mercury lamp (HMW-201KB, manufactured by ORCMANU FACTURING CO., LTD.) at 60 mJ / cm². 2 The irradiation energy exposes the photosensitive layer.

[0180] <Development>

[0181] The polyethylene terephthalate film was peeled off, and a dry film developer (a dry film developer manufactured by Fuji Kiko Co., Ltd.) was used. A 1% by mass Na₂CO₃ aqueous solution at 30°C was sprayed onto the photosensitive resin layer, and the unexposed portions of the photosensitive resin layer were dissolved and removed in a time twice the minimum development time. The minimum development time is defined as the shortest time required for the complete dissolution of the unexposed portions of the photosensitive resin layer.

[0182] 3.2 Evaluation Content

[0183] (1) Sensitivity evaluation

[0184] The photosensitivity of the laminated substrate was evaluated by exposing it for 15 minutes using a 21-level staged exposure table manufactured by Stouffer, which features 21 levels of brightness variation from transparent to black. After exposure, development was performed for twice the minimum development time, based on an exposure level of 8 in the staged exposure table, ensuring complete retention of the resist film. Grading was performed as follows:

[0185] ○: Exposure is 20mJ / cm 2 the following;

[0186] ◎: Exposure is 20mJ / cm 2 -50mJ / cm 2 (excluding end values);

[0187] ●: Exposure intensity is 50mJ / cm 2 above.

[0188] (2) Resolution evaluation

[0189] The laminated substrate was exposed for 15 minutes using a linear pattern mask with a 1:1 width ratio between the exposed and unexposed portions. Development was then performed for twice the minimum development time, with the minimum mask linewidth required for normal formation of cured resist lines used as the resolution value. The following grading was performed:

[0190] ○: Resolution value is below 30μm;

[0191] ◎: Resolution value is 30μm-50μm (excluding end values);

[0192] ●: Resolution value is 50μm or higher.

[0193] (3) Adhesion evaluation

[0194] The laminated substrate is exposed for 15 minutes using a linear pattern mask with a width ratio of 1:100 between the exposed and unexposed portions. Then, it is developed using a development time twice the minimum development time, with the minimum mask linewidth for normal formation of cured resist lines used as the adhesion value.

[0195] ○: Adhesion value is below 30μm;

[0196] ◎: Adhesion value is 30μm-50μm (excluding end value);

[0197] ●: Adhesion value is above 50μm.

[0198] 3.3 Evaluation Results

[0199] The evaluation results are shown in Table 3.

[0200] Table 3

[0201]

[0202]

[0203] When the above-mentioned naphthylpyridine sensitizers of the present invention are applied to photosensitive resin compositions, the compositions exhibit high photosensitivity, high resolution, and high adhesion. These photosensitive resin compositions can be widely used in the manufacture of printed circuit boards, protective patterns, conductor patterns, lead frames, and semiconductor packaging in both dry and wet film forms.

[0204] The above embodiments are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above embodiments. Any changes, modifications, substitutions, combinations, or simplifications made without departing from the spirit and principle of the present invention shall be considered equivalent substitutions and shall be included within the protection scope of the present invention.

Claims

1. A naphthylvinylpyridine compound, characterized in that, The naphthylvinylpyridine compounds have the structure shown in general formula I: General Formula I In the general formula I, R 1 R 2 Each can be independently represented by a halogen, nitro, cyano, or C1~C group. 20 Alkyl, C1~C 10 alkoxy groups, C1~C 10 alkyl ester group, C1~C 20 Any one of the alkylamine groups, and the methylene group in each group may optionally be replaced by an oxygen, sulfur, or imine group; Let a represent any integer from 0 to 4, and b represent any integer from 0 to 3. Given that a is greater than or equal to 2, multiple existing R... 1 Each can be the same or different; when b is greater than or equal to 2, multiple existing R 2 They can be the same or different; m represents any integer from 2 to 3, and n represents any integer from 2 to 3. m and n can be the same or different.

2. The naphthylvinylpyridine compound according to claim 1, characterized in that, In the general formula I, R 1 The R 2 Each can be independently represented by a fluorine group, a chlorine group, a bromine group, a nitro group, a cyano group, or a C1~C1 group. 10 Alkyl groups, C1-C6 alkoxy groups, C1-C6 alkoxy groups 10 It can be any one of the alkylamine group or the alkyl ester group from C1 to C6.

3. The naphthalenevinylpyridine compound according to claim 2, characterized in that, a and b each independently represent any integer from 0 to 2.

4. The naphthalenevinylpyridine compound according to claim 2, characterized in that, In the general formula I, R 1 The R 2 Each of the following can be independently represented as methoxy, ethoxy, propoxy, chloro, bromo, methyl, ethyl, isopropyl, nitro, methyl ester, or cyano, wherein m and n are 2 or 3 respectively; and a and b are 0, 1, or 2 respectively.

5. The naphthalenevinylpyridine compound according to claim 4, characterized in that, The naphthylvinylpyridine compounds are selected from any one of the following compounds: 。 6. The naphthylvinylpyridine compound according to claim 4, characterized in that, In the general formula I, R 1 The R 2 Each can independently represent a chlorine group or a bromine group, where m and n are 2 or 3 respectively, and a and b are 0 or 1 respectively.

7. The naphthylvinylpyridine compound according to claim 6, characterized in that, The naphthylvinylpyridine compounds are selected from any one of the following compounds: 。 8. A photosensitive resin composition, characterized in that, The photosensitive resin composition comprises component A, component B, component C, and component D, wherein component A is an alkali-soluble polymer, component B is a compound having olefinic unsaturated double bonds, component C is a first sensitizer, and component D is a photoinitiator and / or a second sensitizer, wherein the first sensitizer comprises a naphthylvinylpyridine compound as described in any one of claims 1 to 7, and the second sensitizer is of a different type than the first sensitizer.

9. The photosensitive resin composition according to claim 8, characterized in that, In the photosensitive resin composition, the weight content of the first sensitizer is 0.001~10%.

10. The photosensitive resin composition according to claim 9, characterized in that, In the photosensitive resin composition, the weight content of the first sensitizer is 0.005~5%.

11. The photosensitive resin composition according to claim 8, characterized in that, The alkali-soluble polymer is selected from one or more of the group consisting of aliphatic polyurethane (meth)acrylate polymers and aromatic polyurethane (meth)acrylate polymers.

12. The photosensitive resin composition according to claim 11, characterized in that, In the photosensitive resin composition, the alkali-soluble polymer has a weight content of 20-70%.

13. The photosensitive resin composition according to claim 12, characterized in that, In the photosensitive resin composition, the alkali-soluble polymer has a weight content of 30-60%.

14. The photosensitive resin composition according to claim 11, characterized in that, The molecular weight distribution of the alkali-soluble polymer is 1.5 to 6.

0.

15. The photosensitive resin composition according to claim 14, characterized in that, The molecular weight distribution of the alkali-soluble polymer is 2.6~3.

8.

16. The photosensitive resin composition according to claim 8, characterized in that, The compounds having olefinic unsaturated double bonds include compounds obtained by reacting α,β-unsaturated carboxylic acids with polyols, compounds obtained by reacting α,β-unsaturated carboxylic acids with compounds containing glycidyl groups, (meth)acrylate compounds having intramolecular urethane bonds, nonylphenoxypolyethyleneoxyacrylates, γ-chloro-β-hydroxypropyl-β'-(meth)acryloyloxyethyl-phthalate, β-hydroxyethyl-β'-(meth)acryloyloxyethyl-phthalate, β-hydroxypropyl-β'-(meth)acryloyloxyethyl-phthalate, and one or more of the group consisting of alkyl (meth)acrylates.

17. The photosensitive resin composition according to claim 16, characterized in that, The compound having an olefinic unsaturated double bond is selected from (meth)acrylate compounds having an intramolecular urethane bond.

18. The photosensitive resin composition according to claim 16, characterized in that, In the photosensitive resin composition, the compound having olefinic unsaturated double bonds has a weight content of 20-50%.

19. The photosensitive resin composition according to claim 18, characterized in that, In the photosensitive resin composition, the compound having olefinic unsaturated double bonds has a weight content of 25-45%.

20. The photosensitive resin composition according to claim 8, characterized in that, In the photosensitive resin composition, the weight content of component D is 0.01~10%.

21. The photosensitive resin composition according to claim 8, characterized in that, The photosensitive resin composition further includes additives, which include one or more of hydrogen donors, dyes, photochromic agents, fillers, plasticizers, stabilizers, coating aids, and release accelerators.

22. The photosensitive resin composition according to claim 21, characterized in that, In the photosensitive resin composition, the weight content of the additive is 1-10%.

23. A photosensitive resin laminate, characterized in that, The photosensitive resin laminate comprises a photosensitive resin layer formed from the photosensitive resin composition according to any one of claims 8 to 22.

24. A graphical method, the graphical method comprising: A mask is obtained by patterning a photosensitive resin composition, characterized in that the photosensitive resin composition is any one of claims 8 to 22.

25. The graphical method according to claim 24, characterized in that, The graphical method is used in the patterning process of manufacturing printed circuit boards, protective patterns, conductor patterns, lead frames, or semiconductor packages.

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