A silane coupling agent, use thereof, and a photosensitive resin composition comprising the same

Abstract

The application provides a silane coupling agent and application thereof, a photosensitive resin composition containing the same, the silane coupling agent has a structure as shown in formula I, through special design of the molecular structure, on one hand, the silane coupling agent can form stable adhesion with a substrate, on the other hand, the silane coupling agent has excellent heat resistance, good compatibility with resin, strong action, and can form a stable chemical crosslinking network in the resin system in the high-temperature curing process, thereby significantly improving the adhesion, adhesion and close contact of the photosensitive resin composition / photoresist film containing the same and the substrate, and the heat and moisture resistance is excellent, and the reliability of the device is effectively improved. After the photosensitive resin composition containing the silane coupling agent of the application is cured at high temperature, the adhesion of the formed film and the substrate is 5B level, the adhesion of the photoresist film and the substrate is strong, the stability is good, the adhesion is still 5B level after PCT treatment, the heat and moisture resistance is excellent, thereby significantly improving the reliability of the product.

Description

Technical Field

[0001] This invention belongs to the field of photosensitive materials technology, specifically relating to a silane coupling agent and its application, and a photosensitive resin composition containing the same. Background Technology

[0002] With the advancement of electronic communication technology, semiconductor devices and display panels are gradually becoming smaller, thinner, and more flexible, which places increasingly higher demands on product packaging technology and processes. Generally, resin materials such as polyimide and polybenzoxazole are widely used in the packaging of semiconductor and other electronic devices due to their excellent heat resistance, high strength, and other physicochemical properties. Specifically, they are used in redistribution layers (RDL) and bump layers in IC devices, as well as for radiation protection and insulating layers, and in pixel confinement layers (PDL) and planarization layers (PLN) in OLED devices. However, to achieve good performance, resins such as polyimide and polybenzoxazole need to have a high ring-closure rate (close to 100%) to reduce performance defects caused by uncyclic sites (such as uncyclic sites being prone to degradation, leading to molecular bond breakage and resulting in decreased material stability and tensile strength). Furthermore, to improve the adhesion between the film and the substrate, components that enhance adhesion, such as silane coupling agents, are often introduced into the formulation. To achieve a high ring-closure rate, polyimide resins require the resin precursor to be cured at high temperatures (200-500℃), which can easily lead to the decomposition of silane coupling agents and weaken their effectiveness. At the same time, existing silane coupling agents also have the problem of weak interaction with the resin, resulting in insufficient adhesion between the film and the substrate, and the performance cannot be improved.

[0003] To improve the adhesion between the resin and the substrate, developing coupling agents with good heat resistance and strong interaction with the resin film is a key focus of the industry and an urgent problem to be solved. Summary of the Invention

[0004] To address the shortcomings of existing technologies, the present invention aims to provide a silane coupling agent and its application, as well as a photosensitive resin composition containing the same. Through molecular structure design, the silane coupling agent can form a stable bond with the substrate on the one hand, and has good compatibility and strong interaction with the resin matrix on the other hand. It can form a stable chemical crosslinking network in the resin system during high-temperature curing, thereby significantly improving the adhesion between the photosensitive resin composition containing the same and the substrate, and effectively improving the reliability of the device.

[0005] To achieve this objective, the present invention adopts the following technical solution:

[0006] In a first aspect, the present invention provides a silane coupling agent having a structure as shown in Formula I:

[0007]

[0008] In Formula I, R1, R2, and R3 each independently represent a monovalent organic group of C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9).

[0009] In Equation I, R4 is * Represents the linking site of a functional group.

[0010] L represents a divalent organic group of C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.).

[0011] R5 is selected from any one of C1-C8 (e.g., C2, C3, C4, C5, C6 or C7, etc.) straight-chain or branched alkyl groups.

[0012] R6 is -CH2- or phenylene oxide.

[0013] j is 0 or 1; when j is 0, it means that the Si atom in formula I is directly connected to the benzyl ether ring in R4 through a single bond; when j is 1, it means that the Si atom in formula I is connected to R6 in R4.

[0014] h represents the number of *-CH2-O-R5, an integer selected from 1 to 5, for example, 1, 2, 3, 4 or 5; when h≥2, multiple (at least 2) R5s are the same or different groups.

[0015] The silane coupling agent provided by this invention has the structure shown in Formula I, and its molecular structure contains a benzyl ether group R4. During high-temperature curing, it can react with the resin and other additives in the photoresist film (cured from a photosensitive resin composition) to form stable covalent bonds. Simultaneously, the structure contains an alkoxysilane group, which can react with the hydroxyl groups on the substrate surface to form stable Si-O-Si bonds, resulting in excellent adhesion between the photoresist film and the substrate after high-temperature curing. In the silane coupling agent, R4 is... When the structure is the former, there is a flexible chain segment between Si in the molecule and the benzyl ether group, which helps to further improve the adhesion between the resin and the substrate; when the structure is the latter, Si is directly bonded to the aromatic ring, which has better heat resistance. Even when the photoresist film is cured at a relatively high temperature (>300°C), it can maintain a stable structure, and the coupling performance will not decrease due to high-temperature curing (imidization), so that the formed photoresist film has excellent adhesion to the substrate after high-temperature curing. Therefore, through molecular structure design, the silane coupling agent provided by the present invention can form stable adhesion to the substrate on the one hand, and has good compatibility with the resin matrix and strong interaction on the other hand, and can form a stable covalent cross-linking network with components in the resin system during high-temperature curing, thereby significantly improving the adhesion of the photosensitive resin composition / photoresist film containing the same to the substrate, and has excellent heat resistance, effectively improving the comprehensive properties such as reliability of the device.

[0016] In the present invention, unless otherwise specified, the expression of a chemical element includes the concept of isotopes with the same chemical properties. For example, hydrogen (H) includes 1 H (protium), 2 H (deuterium, D), 3 H (tritium, T) and the like; carbon (C) includes 12 C, 13 C and the like.

[0017] In the present invention, the expression "Ca-Cb" means that the number of carbon atoms of the group is a to b; unless otherwise specified, generally the number of carbon atoms does not include the number of carbon atoms of substituents.

[0018] In the present invention, "each independently" means that when there are multiple subjects, they may be the same or different from each other.

[0019] In the present invention, the terms "monovalent organic group", "divalent organic group" and "tetravalent organic group" include any organic group that satisfies the chemical environment.

[0020] In the present invention, the expression of a ring structure crossed by "—" means that the connection site is located at any bondable position on the ring structure.

[0021] Preferably, R1, R2 and R3 are each independently selected from any one of C1-C10 (such as C2, C3, C4, C5, C6, C7, C8 or C9, etc.) linear or branched alkyl groups, more preferably any one of C1-C6 linear or branched alkyl groups, exemplary examples include, but are not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl and the like.

[0022] Preferably, the L is selected from C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, or C18, etc.) straight-chain or branched alkylene groups, or one or at least two (e.g., 2, 3, or 4, etc.) of the C1-C20 straight-chain or branched alkylene groups -CH2- with -O-, -S-, -NR. N1 Any one of the following groups: -, -CO-, C6-C20 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) arylene-substituted groups.

[0023] R N1 It is selected from hydrogen, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8 or C9, etc.) straight-chain or branched alkyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) aryl, and is further preferably hydrogen.

[0024] Preferably, the L is selected from C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8 or C9, etc.) straight-chain alkylene groups, or any one or at least two (e.g., 2, 3 or 4, etc.) of the C1-C10 straight-chain alkylene groups that are replaced by -O-, -NH-, -CO-, or phenylene groups.

[0025] Preferably, R4 is selected from any one of the following structures:

[0026] In this context, * represents the linking site of a functional group.

[0027] i and x represent the number of -CH2-, where i is an integer from 1 to 7, for example, 1, 2, 3, 4, 5, 6 or 7; x is an integer from 0 to 7, for example, 1, 2, 3, 4, 5, 6 or 7.

[0028] Preferably, R5 is selected from any one of C1-C6 (e.g., C1, C2, C3, C4, C5 or C6) straight-chain or branched alkyl groups, and more preferably methyl.

[0029] Preferably, h is an integer from 1 to 3.

[0030] Preferably, R4 is selected from... Any of the above, * represents the linking site of the group.

[0031] In a second aspect, the present invention provides the application of the silane coupling agent as described in the first aspect in photosensitive materials.

[0032] Thirdly, the present invention provides a photosensitive resin composition comprising a combination of an alkali-soluble resin, a photosensitive compound, and a silane coupling agent as described in the first aspect.

[0033] Preferably, the alkali-soluble resin includes any one or a combination of at least two of the following: polyimide precursor resin, polyamic acid-polyimide copolymer, polyisoimide-polyamic acid copolymer, polyisoimide, or polyimide.

[0034] Preferably, the alkali-soluble resin comprises at least one of the structural units shown in Formula II, Formula III, or Formula IV:

[0035]

[0036] Among them, R 10 R 12 R 14 R 16 Each can independently represent a tetravalent organic group of C4-C60 (e.g., C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C35, C36, C38, C40, C42, C45, C48, C50, C52, C55, or C58, etc.).

[0037] R 11 R 13 R 15 R 17 Each can independently represent a divalent organic group of C3-C60 (e.g., 4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C35, C36, C38, C40, C42, C45, C48, C50, C52, C55, or C58, etc.).

[0038] R 18 R 19 Each is independently selected from any one of the straight-chain or branched alkyl groups of C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8 or C9, etc.).

[0039] The photosensitive resin composition provided by the present invention includes a combination of an alkali-soluble resin, a photosensitive compound, and a silane coupling agent as described in the first aspect; wherein the silane coupling agent has good compatibility and strong interaction with the alkali-soluble resin, and has excellent heat resistance. On the one hand, it can react with the hydroxyl groups on the substrate surface to form stable siloxane bonds; on the other hand, it can react with other components such as the alkali-soluble resin during high-temperature curing (curing and / or imidization) to generate a stable covalent cross-linked network. As a result, the photoresist film formed by the photosensitive resin composition has excellent adhesion and bonding to the substrate, effectively improving the reliability of the device.

[0040] As a preferred embodiment of the present invention, the alkali-soluble resin includes any one or a combination of at least two of the following: polyimide precursor resin (polyamic acid and / or polyamic ester, preferably containing the structural unit shown in Formula II), polyamic acid-polyimide copolymer (preferably containing the structural unit shown in Formula III), or polyimide (preferably containing the structural unit shown in Formula IV).

[0041] Preferably, the number of structural units shown in Formula II in the alkali-soluble resin is f, and the number of structural units shown in Formula IV is g, wherein f and g are each an independent integer from 2 to 200, such as 3, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 60, 70, 80, 90, 100, 110, 130, 150, 170 or 190, etc.

[0042] Preferably, the structural unit of formula III in the alkali-soluble resin includes a polyimide segment. and polyamic acid (polyamic acid ester) fragments The two fragments are connected by chemical bonds, and their number is an independent integer from 2 to 200, such as 3, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 60, 70, 80, 90, 100, 110, 130, 150, 170 or 190, etc.

[0043] Preferably, the R 10 R 12 R 14 R 16 Each group is independently selected from any one of the following: substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) tetravalent aromatic groups, or substituted or unsubstituted C4-C20 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) tetravalent alicyclic groups.

[0044] R 10 R12 R 14 R 16 The substituents described herein are each independently selected from at least one of halogen, hydroxyl, unsubstituted or halogenated C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) straight-chain or branched alkyl, and unsubstituted or halogenated C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) alkoxy.

[0045] Preferably, the "substituted or unsubstituted" group can replace one substituent or multiple substituents. When there are multiple substituents (at least two), they can be the same or different substituents. The same expression used below has the same meaning, and the selection range of substituents is as shown above, and will not be repeated hereafter.

[0046] In this invention, the C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) tetravalent aromatic groups include C6-C30 aryl groups (e.g., phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, anthracene, phenanthrene, triphenylene, tetraphenyl, etc.) or aryl groups linked by bridging bonds (single bonds, O, S, sulfoxide, sulfone, substituted or unsubstituted alkylene, etc.). Similar examples exist for "C6-C30 divalent aromatic groups" as described below.

[0047] The C4-C20 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) tetravalent alicyclic groups, where "alicyclic group" refers to a non-aromatic saturated or unsaturated cyclic structure, including monocyclic, bridged, spirocyclic, or fused rings, exemplarily including but not limited to: cyclobutyl, cyclopentyl, cyclohexyl, bicyclooctyl, etc. Similar examples are given for "C4-C20 divalent alicyclic groups" mentioned below.

[0048] The C1-C20 straight-chain or branched alkyl groups can be straight-chain or branched alkyl groups of C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.; exemplary, including but not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, n-heptyl, n-nonyl or n-decyl, etc.

[0049] Specific examples of the C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) alkoxy groups can be exemplified by the monovalent groups obtained by attaching the above-mentioned straight-chain or branched alkyl groups to O.

[0050] In this invention, the halogen includes fluorine, chlorine, bromine or iodine; the term "halogen substitution" means that at least one hydrogen atom in the group is substituted by a halogen (fluorine, chlorine, bromine or iodine), preferably fluorine substitution.

[0051] Preferably, the R 10 R 12 R 14 R 16 Each group is independently selected from any one of the following groups:

[0052] In this context, * represents the linking site of a functional group.

[0053] R 21 R 22 R 23 R 24 R 25 R 26 Each is independently selected from hydrogen, halogen, hydroxyl, unsubstituted or halogenated C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) straight-chain or branched alkyl, unsubstituted or halogenated C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) alkoxy, and more preferably hydrogen, fluorine, methyl, methoxy, perfluoromethyl or perfluoromethoxy.

[0054] L 21 Selected from single bonds, -O-, -S-, and sulfone groups sulfoxide Unsubstituted or R'-substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9, etc.) straight-chain or branched alkylene groups; unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C16, or C18, etc.) arylene groups; *-L 22 -Ar 21 -L 23 Any one of -*.

[0055] L 22 L 23Each is independently selected from any one of the following: -O-, -S-, sulfone, sulfoxide, unsubstituted or R'-substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8 or C9, etc.) straight-chain or branched alkylene groups.

[0056] Ar 21 It is selected from any one of the unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C16, or C18, etc.) arylene groups.

[0057] R' is selected from at least one of halogen, hydroxyl, unsubstituted or halogenated C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) straight-chain or branched alkyl, and unsubstituted or halogenated C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) alkoxy.

[0058] Preferably, the L 21 Selected from single bond, -O-, -CH2-、 Any one of them.

[0059] Preferably, the R 10 R 12 R 14 R 16 Each group is independently selected from any one of the following groups:

[0060]

[0061] In this context, * represents the linking site of a functional group.

[0062] Preferably, the R 11 R 13 R 15 R 17 Each group is independently selected from any one of the groups shown in Formula V, substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) divalent aromatic groups, or substituted or unsubstituted C4-C20 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) divalent alicyclic groups.

[0063] R 11 R13 R 15 R 17 The substituents described herein are each independently selected from at least one of halogen, hydroxyl, unsubstituted or halogenated C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) straight-chain or branched alkyl, and unsubstituted or halogenated C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) alkoxy.

[0064]

[0065] * Represents the linking site of a functional group.

[0066] A is selected from any one of the following: single bond, -O-, -S-, sulfone, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8 or C9, etc.) divalent aliphatic hydrocarbon group, substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C7, C8, C9, C10, C12, C14, C15, C17 or C18, etc.) divalent alicyclic group, and substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) divalent aromatic group.

[0067] The substituents described in A are each independently selected from at least one of the following: halogen, unsubstituted or halogenated C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9, etc.) straight-chain or branched alkyl, unsubstituted or halogenated C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) aryl, and unsubstituted or halogenated C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) phenolic groups.

[0068] R 31 R 32Each group is independently selected from any one of the following: halogen, nitro, cyano, carboxyl, unsubstituted or halogenated C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9, etc.) straight-chain or branched alkyl, unsubstituted or halogenated C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9, etc.) alkoxy, unsubstituted or halogenated C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) aryl, amide, benzyl ether, or benzyl alcohol.

[0069] R 33 R 34 Each is independently selected from any one of the following: C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9, etc.) straight-chain or branched alkylene groups; C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9, etc.) alkeneoxy groups; and C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9, etc.) containing a divalent Si group.

[0070] R 35 R 36 Each is independently selected from *-CH2-OC m H 2m+1 m is an integer from 0 to 8, for example, it can be 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0071] R 37 R 38 Each group is independently selected from any one of the following: halogen, hydroxyl, nitro, cyano, carboxyl, unsubstituted or halogenated C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9, etc.) straight-chain or branched alkyl, unsubstituted or halogenated C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9, etc.) alkoxy, unsubstituted or halogenated C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) aryl, and C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9, etc.) ester or amide.

[0072] k1, k2, s1, s2, p1, p2, q1, and q2 are each independently selected from integers between 0 and 4, for example, they can be 0, 1, 2, 3, and 4.

[0073] n1 and n2 are each independently 0 or 1; when n1 and n2 are 0, it means that the benzene ring is directly connected to -CO- through a single bond.

[0074] Preferably, A in Formula V is selected from any one of sulfone, substituted or unsubstituted C1-C6 (e.g., C1, C2, C3, C4, C5 or C6) straight-chain or branched alkylene groups; the substituents in A are each independently selected from at least one of halogen, phenol, unsubstituted or halogenated C1-C6 (e.g., C1, C2, C3, C4, C5 or C6) straight-chain or branched alkyl, and unsubstituted or halogenated C1-C6 (e.g., C1, C2, C3, C4, C5 or C6) alkoxy groups.

[0075] More preferably, A in formula V is selected from sulfone groups,

[0076] Preferably, R in formula V 33 R 34 Each is independently selected from any one of C1-C6 (e.g., C1, C2, C3, C4, C5 or C6) straight-chain or branched alkylene groups, and C1-C6 (e.g., C1, C2, C3, C4, C5 or C6) alkoxides, and more preferably *-CH2-*, *-CH2-O-* or *-O-CH2-*.

[0077] Preferably, R in formula V 35 R 36 Each can be independently represented as *-CH2-OH or *-CH2-O-CH3.

[0078] Preferably, p1, p2, q1, and q2 in formula V are each independently selected from integers from 1 to 3, and more preferably 1 or 2.

[0079] Preferably, the group represented by formula V has any one of the following structures:

[0080]

[0081]

[0082] In this context, * represents the linking site of a functional group.

[0083] Preferably, the R 11 R 13 R 15 R 17 Each is independently selected from the groups shown in Formula V. Any one of them;

[0084] In this context, * represents the linking site of a functional group.

[0085] R 41 R 42Each is independently selected from any one of halogen, hydroxyl, unsubstituted or halogenated C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C12, C15, C17 or C19, etc.) straight-chain or branched alkyl, unsubstituted or halogenated C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C12, C15, C17 or C19, etc.) alkoxy, and more preferably hydroxyl, fluorine, methyl, methoxy, perfluoromethyl or perfluoromethoxy.

[0086] L 41 Selected from single bonds, -O-, -S-, sulfones, sulfoxides, unsubstituted or halogenated C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9, etc.) straight-chain or branched alkylene groups, unsubstituted or halogenated C6-C20 (e.g., C6, C9, C10, C12, C14, C16, or C18, etc.) arylene groups, *-L 42 -Ar 41 -L 43 Any one of -*.

[0087] L 42 L 43 Each is independently selected from any one of the following: -O-, -S-, sulfone, sulfoxide, unsubstituted or halogenated C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8 or C9, etc.) straight-chain or branched alkylene groups.

[0088] Ar 41 Selected from any one of the unsubstituted or R”-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C16 or C18, etc.) arylene groups.

[0089] "R" is selected from any one of halogen, hydroxyl, unsubstituted or halogenated C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8 or C9) straight-chain or branched alkyl, and unsubstituted or halogenated C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8 or C9) alkoxy.

[0090] u1 and u2 are each independently selected from integers from 0 to 4, for example, they can be 0, 1, 2, 3 or 4.

[0091] Preferably, the L 41 Selected from single bond, -O-, -CH2-、 Any one of them.

[0092] Preferably, the R 11 R 13R 15 R 17 Each is independently selected from the groups shown in Formula V.

[0093]

[0094] Any one of them;

[0095] * Represents the linking site of a functional group.

[0096] Preferably, the weight-average molecular weight of the alkali-soluble resin is 2,000-100,000, for example, it can be 3,000, 5,000, 8,000, 10,000, 15,000, 20,000, 25,000, 30,000, 35,000, 40,000, 45,000, 50,000, 55,000, 60,000, 70,000, 80,000, or 90,000, and more preferably 5,000-50,000.

[0097] Preferably, the alkali-soluble resin includes a polyimide precursor resin (polyamic acid and / or polyamic acid ester, preferably containing the structural unit shown in Formula II), which can be prepared in a manner known in the art, exemplarily including the following routes: (1) directly polymerizing a diamine with a dianhydride to obtain polyamic acid, and then esterifying it to generate polyamic acid ester; (2) reacting a dianhydride with an alcohol to generate a dicarboxylic acid diester, and then reacting it with thionyl chloride to generate a diacyl chloride diester, and then polymerizing it with a diamine compound to obtain polyamic acid ester; (3) reacting a dianhydride with an alcohol to generate a dicarboxylic acid diester, and then reacting it with a diamine compound in the presence of a dehydrating agent such as cyclohexylcarbodiimide to obtain polyamic acid ester.

[0098] Preferably, the preparation method of the polyimide precursor resin includes: firstly, reacting a diamine monomer (NH2-R) with a diamine monomer (NH2-R) 11 -NH2) and dianhydride monomers Polymerization yields polyamic acid; the polyamic acid is then subjected to esterification to obtain the polyimide precursor resin.

[0099] Preferably, the reagents for the esterification reaction include N,N-dimethylformamide dimethyl acetal.

[0100] Preferably, the polyimide precursor resin may have end-capping agents introduced into its end groups. In order to further improve performance, the end-capping agents may have alkenyl, alkynyl, benzyl ether, benzyl alcohol, and other groups introduced into them. In the subsequent curing process, the strength and other properties of the film are improved through cross-linking reaction.

[0101] Preferably, the capping agent includes, but is not limited to:

[0102] Preferably, the photosensitive compound is a compound containing a diazonoquinone group.

[0103] Preferably, the structure of the diazonoquinone group is as follows: * Represents the linking site of a functional group.

[0104] Preferably, the photosensitive resin composition further includes a crosslinking agent.

[0105] Preferably, the photosensitive resin composition further includes solvents and / or other additives.

[0106] Preferably, the solvent is a solvent commonly used in the art, including but not limited to any one or a combination of at least two of γ-butyrolactone, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monomethyl ether formate, propylene glycol monoethyl ether formate, ethyl lactate, butyl lactate, N-methylpyrrolidone, N,N-dimethylformamide or N,N-dimethylacetamide.

[0107] Preferably, the other additives include other silane coupling agents and / or surfactants.

[0108] In this invention, "other silane coupling agents" refers to silane coupling agents other than the silane coupling agents with the structure shown in Formula I provided by this invention.

[0109] The other silane coupling agents, in addition to containing alkoxysilyl groups, also contain at least one active functional group; preferably, the other silane coupling agents contain at least one of vinyl, allyl, oxocyclic, styryl, acyloxy, acryloyloxy, urea, amino, imidazole, tertiary amine, secondary amine, mercapto, or isocyanate groups.

[0110] Preferably, the surfactant includes any one or a combination of at least two of the following: fluorinated surfactants, polyethylene glycol surfactants, or surfactants with a siloxane structure.

[0111] Preferably, the other additives help to improve the flatness of the film, further improve the adhesion between the photoresist film and the substrate, and reduce residual film after development.

[0112] Preferably, the other additives also include photoacid-generating agents, thermal acid-generating agents, photoalkali-generating agents, thermal alkali-generating agents, etc., which can promote the crosslinking reaction between the resin and the crosslinking agent and / or the ring-closing reaction of the resin during the curing process.

[0113] Preferably, the photosensitive resin composition comprises the following components in weight percentage:

[0114]

[0115] The alkali-soluble resin has a mass percentage content of 4-30%, for example, it can be 5%, 6%, 8%, 10%, 12%, 15%, 18%, 20%, 22%, 25% or 28%, and is more preferably 5-20%.

[0116] The mass percentage of the photosensitive compound is 0.4-8%, for example, it can be 0.5%, 0.8%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, 5%, 5.5%, 6%, 6.5%, 7% or 7.5%, etc.

[0117] The silane coupling agent having the structure shown in Formula I has a mass percentage content of 0.001-0.5%, for example, it can be 0.003%, 0.005%, 0.008%, 0.01%, 0.03%, 0.05%, 0.08%, 0.1%, 0.15%, 0.2%, 0.25%, 0.3%, 0.35%, 0.4%, or 0.45%, etc.

[0118] The mass percentage of the crosslinking agent is 0.4-10%, for example, it can be 0.5%, 0.8%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, 5%, 5.5%, 6%, 6.5%, 7%, 7.5%, 8%, 8.5%, 9% or 9.5%, etc.

[0119] The other additives have a mass percentage content of 0.001-0.5%, for example, 0.005%, 0.008%, 0.01%, 0.03%, 0.05%, 0.08%, 0.1%, 0.15%, 0.2%, 0.25%, 0.3%, 0.35%, 0.4%, or 0.45%, etc.

[0120] The solvent has a mass percentage content of 55-95%, for example, it can be 58%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or 93%, etc.

[0121] Preferably, the solid content of the photosensitive resin composition is 5-45%, more preferably 8-30%. Too low a solid content is not conducive to forming a continuous film with a certain thickness, while too high a solid content may lead to excessive viscosity, which in turn leads to problems such as bubbles and poor smoothness during the coating process.

[0122] Fourthly, the present invention provides the application of the photosensitive resin composition as described in the third aspect in a flat panel display device or a semiconductor device.

[0123] Preferably, the photosensitive resin composition is used as a stress buffer material for semiconductor devices, a passivation layer, a pixel defining layer in display devices, a planarization layer, etc.

[0124] Preferably, the photosensitive resin composition can form a cured film after coating, pre-baking, photolithography, development and curing, which is permanently retained in semiconductor devices or flat panel display devices (display panels). The cured film has excellent substrate adhesion and can be used in the packaging process of flexible semiconductors, flat panel displays and other devices.

[0125] Compared with the prior art, the present invention has the following beneficial effects:

[0126] (1) The silane coupling agent provided by the present invention has the structure shown in Formula I. Through the special design of the molecular structure, it can form a stable bond with the substrate on the one hand, and has excellent heat resistance on the other hand. It has good compatibility with resin and strong interaction force. It can form a stable chemical cross-linking network in the resin system during high temperature curing, thereby significantly improving the adhesion, bonding force and adhesion between the photosensitive resin composition / photoresist film containing it and the substrate. Moreover, it has excellent heat and moisture resistance, effectively improving the reliability of the device.

[0127] (2) After the photosensitive resin composition containing the silane coupling agent is cured at high temperature, the adhesion between the film formed and the substrate is 5B level. The photoresist film has strong adhesion to the substrate and good stability. It still maintains excellent adhesion at 5B level after PCT high temperature steam treatment and has excellent resistance to damp heat, thereby significantly improving the reliability of the product. Detailed Implementation

[0128] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention in any way.

[0129] In one specific embodiment, the silane coupling agent having the structure shown in Formula I can be prepared using the following synthetic route A, synthetic route B, or synthetic route C:

[0130] Synthetic route A: R4 is The specific method is as follows:

[0131] Synthesis Route B: R4 is The specific method is as follows:

[0132] Synthetic route C: R4 is Y is either O or NH, and the specific method is as follows:

[0133]

[0134] In the aforementioned synthetic route, U1 and U2 are each independently selected from halogens, preferably chlorine, bromine or iodine; R1, R2, R3, R5, and h have the same limited range as in Formula I; i is selected from integers from 1 to 7.

[0135] The preparation method of the silane coupling agent shown in Formula I of this invention includes, but is not limited to, the above synthesis method. Those skilled in the art can also make conventional adjustments to the preparation method according to actual needs. Silane coupling agents with the structure shown in Formula I obtained by other methods are also within the protection scope of this invention.

[0136] The present invention provides exemplary synthetic methods for representative silane coupling agents through the following synthetic examples. The solvents and reagents used in the synthetic examples can be purchased from the chemical product market or custom-made. The product structures in the synthetic examples were tested using a ZAB-HS mass spectrometer (manufactured by Micromass, UK).

[0137] Synthesis example 1

[0138] A silane coupling agent A1, with the following structure: The specific synthesis method is as follows:

[0139] Under nitrogen protection, 164 g of methyl orthosilicate and 0.5 mol of metallic sodium were added to a three-necked flask. The sodium was heated and stirred to break it into sodium sand. Then, a mixed solution of 0.5 mol of 1-chloro-4-(methoxymethyl)benzene and 0.6 mol of trimethoxychlorosilane was added dropwise to the three-necked flask at 105 °C. After the addition was complete, the reaction was continued for 1.5 h. The crude product was obtained by vacuum distillation. The crude product was purified by column chromatography to obtain the silane coupling agent A1. Mass spectrometry results: m / z value (M+1): 243.

[0140] Synthesis example 2

[0141] A silane coupling agent A2, with the following structure: The specific synthesis method differs from that of Synthesis Example 1 only in that 1-chloro-4-(methoxymethyl)benzene is replaced with an equimolar amount of 4-chloro-1,2-bis(methoxymethyl)benzene. All other raw materials and process parameters are the same as those in Synthesis Example 1, and the silane coupling agent A2 is obtained. Mass spectrometry test results: m / z value (M+1): 287.

[0142] Synthesis example 3

[0143] A silane coupling agent A3, with the following structure: The specific synthesis method is as follows:

[0144] Palladium acetate (0.004 mol), 2-(di-tert-butylphosphine)biphenyl (0.01 mol), sodium tert-butoxide (0.2 mol), anhydrous toluene (75 mL), and γ-aminopropyltrimethoxysilane (0.1 mol) were added to a 250 mL three-necked glass flask. After deoxygenation, a nitrogen gas flow was purged for protection. An anhydrous toluene solution (75 mL) of 0.08 mol of 1-bromo-4-(methoxymethyl)benzene was added dropwise to the reaction system. The reaction mixture was heated to 80 °C, and the content of 1-bromo-4-(methoxymethyl)benzene in the reaction system was monitored by gas chromatography-mass spectrometry (GC-MS). The reaction was stopped after the reaction was complete and allowed to cool naturally to room temperature. The reaction solution was diluted with dichloromethane, and the solid components were removed by diatomaceous earth filtration. The solvent was removed by rotary evaporation. The crude product was purified by column chromatography to obtain the silane coupling agent A3. Mass spectrometry results: m / z value (M+1): 300.

[0145] Synthesis example 4

[0146] A silane coupling agent A4, with the following structure: The specific synthesis method differs from that of Synthesis Example 3 only in that 1-bromo-4-(methoxymethyl)benzene is replaced with an equimolar amount of 4-bromo-1,2-bis(methoxymethyl)benzene. All other raw materials and process parameters are the same as those in Synthesis Example 3, and the silane coupling agent A4 is obtained. Mass spectrometry test results: m / z value (M+1): 344.

[0147] Synthesis example 5

[0148] A silane coupling agent A5, with the following structure: The specific synthesis method is as follows:

[0149] Anhydrous toluene (75 mL) and γ-aminopropyltrimethoxysilane (0.1 mol) were added to a 250 mL three-necked glass flask, and after deoxygenation, a nitrogen gas flow was purged for protection. Anhydrous toluene solution (75 mL) of 0.95 mol of 1-isocyanate-4-(methoxymethyl)benzene was added dropwise to the reaction system. The reaction mixture was heated to 60 °C and reacted for 24 h, then naturally cooled to room temperature. The reaction solution was diluted with dichloromethane, filtered through diatomaceous earth, and the solvent was removed by rotary evaporation. The crude product was purified by column chromatography to obtain the silane coupling agent A5; mass spectrometry results: m / z value (M+1): 343.

[0150] Synthesis example 6

[0151] A silane coupling agent A6, with the following structure: The specific synthesis method is as follows:

[0152] Anhydrous toluene (75 mL) and γ-hydroxypropyltrimethoxysilane (0.1 mol) were added to a 250 mL three-necked glass flask, and the mixture was deoxygenated and protected with a nitrogen stream. Anhydrous toluene solution (75 mL) of 0.95 mol of 1-isocyanate-4-(methoxymethyl)benzene was added dropwise to the reaction system. The reaction mixture was heated to 60 °C and reacted for 24 h, then naturally cooled to room temperature. The reaction solution was diluted with dichloromethane, filtered through diatomaceous earth, and the solvent was removed by rotary evaporation. The crude product was purified by column chromatography to obtain the silane coupling agent A6. Mass spectrometry results: m / z value (M+1): 344.

[0153] Synthesis Example 7

[0154] A silane coupling agent A7, with the following structure: The specific synthesis method is as follows:

[0155] Anhydrous toluene (75 mL) and 4-((trimethoxysilyl)propyl)phenol (0.1 mol) were added to a 250 mL three-necked glass flask. After deoxygenation, a nitrogen gas flow was purged for protection. Anhydrous toluene solution (75 mL) of 0.95 mol of 1-isocyanate-4-(methoxymethyl)benzene was added dropwise to the reaction system. The reaction mixture was heated to 60 °C and reacted for 24 h, then naturally cooled to room temperature. The reaction solution was diluted with dichloromethane, filtered through diatomaceous earth, and the solvent was removed by rotary evaporation. The crude product was purified by column chromatography to obtain the silane coupling agent A7. Mass spectrometry results: m / z value (M+1): 420.

[0156] In the following specific embodiments of the present invention, the weight-average molecular weight of the alkali-soluble resin was obtained by gel permeation chromatography (GPC) using a Viscotek gel permeation chromatograph from Malvern Corporation with a D6000M column.

[0157] Preparation Example 1

[0158] An alkali-soluble resin B1, specifically a polyimide precursor resin, is prepared as follows:

[0159] Under nitrogen protection, 6.04 g of diamine compound 1 was dissolved in 20 mL of N-methylpyrrolidone (NMP), and the mixture was cooled to 0 °C. A mixture of 3.87 g of 3,3,4,4-diphenyl ether tetracarboxylic anhydride and 12 g of anhydrous NMP was rapidly added to the reaction system, and the reaction was maintained at 0 °C for 5 h. The temperature was then raised to 60 °C, and 2.68 g of N,N-dimethylformamide dimethyl acetal was slowly added dropwise to the reaction system. The reaction was maintained at 60 °C for 2 h, and the mixture was cooled to room temperature. The reaction solution was poured into 300 mL of deionized water, filtered, and the precipitate was collected. The precipitate was then vacuum dried at 50 °C for 24 h to obtain the alkali-soluble resin B1, with a weight-average molecular weight of 8500.

[0160] Diamine compound 1:

[0161] Preparation Example 2

[0162] An alkali-soluble resin B2, specifically a polyimide precursor resin, is prepared in a method that differs from that of Preparation Example 1 only in that diamine compound 1 is replaced with an equimolar amount of diamine compound 2. All other raw materials and process parameters are the same as in Preparation Example 1, resulting in the alkali-soluble resin B2 with a weight-average molecular weight of 8300.

[0163] Diamine compound 2:

[0164] Preparation Example 3

[0165] An alkali-soluble resin B3, specifically a polyimide precursor resin, is prepared as follows:

[0166] Under nitrogen protection, 0.692 g of diamine compound 3 and 5.44 g of diamine compound 2 were dissolved in 20 mL of NMP. The mixture was cooled to 0 °C, and a mixture of 3.87 g of 3,3,4,4-diphenyl ether tetracarboxylic anhydride and 12 g of NMP was rapidly added to the reaction system. The reaction was maintained at 0 °C for 5 h. The temperature was then raised to 60 °C, and 2.68 g of N,N-dimethylformamide dimethyl acetal was slowly added dropwise to the reaction system. The reaction was maintained at 60 °C for 2 h. The mixture was cooled to room temperature, and the reaction solution was poured into 300 mL of deionized water. The precipitate was collected by filtration and dried under vacuum at 50 °C for 24 h to obtain the alkali-soluble resin B3 with a weight-average molecular weight of 8500.

[0167] Diamine compound 3:

[0168] Preparation Example 4

[0169] An alkali-soluble resin B4, specifically a polyimide precursor resin, is prepared as follows:

[0170] Under nitrogen protection, 1.10 g of 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane and 1.00 g of 4,4-diaminodiphenyl ether were dissolved in 15 mL of NMP. The mixture was cooled to 0 °C, and a mixture of 2.92 g of 3,3,4,4-diphenyl ether tetracarboxylic anhydride and 8 g of NMP was rapidly added to the reaction system. The reaction was maintained at 0 °C for 5 h. The temperature was then raised to 60 °C, and 2.68 g of N,N-dimethylformamide dimethyl acetal was slowly added dropwise to the reaction system. The reaction was maintained at 60 °C for 2 h, and the mixture was cooled to room temperature. The reaction solution was poured into 300 mL of deionized water, filtered, and the precipitate was collected. The precipitate was then vacuum dried at 50 °C for 24 h to obtain the alkali-soluble resin B4 with a weight-average molecular weight of 8400.

[0171] Preparation Example 5

[0172] An alkali-soluble resin B5, specifically a polyamic acid-polyimide copolymer resin, is prepared as follows:

[0173] Under nitrogen protection, 1.10 g of 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane and 1.00 g of 4,4-diaminodiphenyl ether were dissolved in 15 mL of NMP. The mixture was cooled to 0 °C, and a mixture of 2.92 g of 3,3,4,4-diphenyl ether tetrahydric anhydride and 8 g of NMP was rapidly added to the reaction system. The reaction was maintained at 0 °C for 5 h. While maintaining 0 °C, 0.7 g of N,N'-diisopropylcarbodiimide and 0.01 g of 4-dimethylaminopyridine were added to the reaction system. After reacting for 10 h, the reaction solution was poured into 300 mL of deionized water, filtered, and the precipitate was collected. The precipitate was then vacuum dried at 50 °C for 24 h to obtain the alkali-soluble resin B5, with a weight-average molecular weight of 8300.

[0174] Example 1

[0175] A photosensitive resin composition comprising the following components: 10g of alkali-soluble resin B1 provided in Preparation Example 1, 2g of photosensitive compound, 1.5g of crosslinking agent, 0.1g of fluorinated surfactant, 0.08g of silane coupling agent A1 provided in Synthesis Example 1, and 85g of γ-butyrolactone.

[0176] Among them, photosensitive compounds are Q is * Represents the linkage site of a functional group; the crosslinking agent is...

[0177] The photosensitive resin composition is prepared as follows: all components are mixed and fully dissolved according to the formula to obtain the photosensitive resin composition.

[0178] Examples 2-25, Comparative Examples 1-3

[0179] A photosensitive resin composition differs from Example 1 only in the type of alkali-soluble resin and / or the amount of other components; the types and amounts of other components are the same as in Example 1, and the specific components are shown in Table 1.

[0180] Table 1

[0181]

[0182]

[0183] In Table 1, "--" indicates that the component was not added; KBM-573 and KBM-503 are silane coupling agents purchased from Shin-Etsu Chemical.

[0184] The performance of the photosensitive resin compositions provided in Examples 1-25 and Comparative Examples 1-3 was tested, and the specific methods are as follows:

[0185] (1) Adhesion test

[0186] Adhesion Test 1: The photosensitive resin compositions provided in Examples 1-6 and Comparative Examples 1-3 were applied to a 4-inch square ITO glass substrate using a spin coating method (250 rpm). The substrate was pre-baked at 120°C for 180 seconds to remove most of the solvent. It was then exposed without a mask in a UV exposure machine to promote the decomposition of the photosensitive compound. After that, the coated glass substrate was placed in a clean oven at 320°C under nitrogen protection (oxygen concentration <20 ppm) for 60 minutes for curing. After removal, the substrate was tested according to ASTM D3359. An adhesion of 5B was considered excellent, 4B was considered acceptable, and 3B or below was considered unacceptable.

[0187] Adhesion Test 2: The photosensitive resin compositions provided in Examples 7-25 and Comparative Examples 1-3 were applied to a 4-inch square ITO glass substrate using a spin coating method (250 rpm). The substrate was pre-baked at 120°C for 180 seconds to remove most of the solvent. It was then exposed without a mask in a UV exposure machine to promote the decomposition of the photosensitive compound. After that, the coated glass substrate was placed in a clean oven at 270°C under nitrogen protection (oxygen concentration <20 ppm) for 60 minutes for curing. After removal, the prepared glass substrate was tested according to the method of ASTM D3359. An adhesion of 5B is considered excellent, 4B is considered acceptable, and 3B or below is considered unacceptable.

[0188] (2) Reliability Testing

[0189] The samples prepared according to the adhesion test method in (1) (Examples 1-6 were tested according to the method of "Adhesion Test 1", Examples 7-25 were tested according to the method of "Adhesion Test 2", and Comparative Examples 1-3 were tested under both methods) were marked with a grid according to the method of ASTM D3359. The samples were then placed in a high-pressure steam sterilizer at 121°C and 2 atm for 100 hours (PCT treatment). After cooling to room temperature, the samples were taken out and the adhesion was tested according to the method of ASTM D3359. An adhesion of 5B is considered excellent, 4B is considered acceptable, and 3B or below is considered unacceptable.

[0190] The test results of Examples 1-6 and Comparative Examples 1-3 (sample preparation method is the method in "Adhesion Test 1") are shown in Table 2, and the test results of Examples 7-25 and Comparative Examples 1-3 (sample preparation method is the method in "Adhesion Test 2") are shown in Table 3.

[0191] Table 2

[0192] Example 1 excellent excellent Example 2 excellent excellent Example 3 excellent excellent Example 4 excellent excellent Example 5 excellent excellent Example 6 excellent excellent Comparative Example 1 Unqualified Unqualified Comparative Example 2 Unqualified Unqualified Comparative Example 3 Unqualified Unqualified

[0193] Table 3

[0194] Example 7 excellent excellent Example 8 excellent excellent Example 9 excellent excellent Example 10 excellent excellent Example 11 excellent excellent Example 12 excellent excellent Example 13 excellent excellent Example 14 excellent excellent Example 15 excellent excellent Example 16 excellent excellent Example 17 excellent excellent Example 18 excellent excellent Example 19 excellent excellent Example 20 excellent excellent Example 21 excellent excellent Example 22 excellent excellent Example 23 excellent excellent Example 24 excellent excellent Example 25 excellent excellent Comparative Example 1 qualified Unqualified Comparative Example 2 Unqualified Unqualified Comparative Example 3 qualified Unqualified

[0195] Based on the above performance data, it can be seen that compared with existing silane coupling agents (such as Comparative Examples 1-3, KBM-503), the silane coupling agent provided by this invention, after being used in photosensitive resin compositions and cured into films, significantly improves the adhesion to the substrate, forming a clear technical advantage. The reason for this is that the silane coupling agent of this invention introduces a benzene ring-containing structure, which effectively improves the heat resistance of the coupling agent. Simultaneously, due to the introduction of benzyl ether groups in the structure, during high-temperature curing, the benzyl ether groups can react with the components in the photoresist film to form strong covalent bonds, enhancing the interaction force between the photoresist film and the substrate, thereby improving the adhesion of the film to the substrate. For Examples 1-6, the two silane coupling agents A1 and A2, after curing, are mainly composed of heat-resistant aromatic rings and siloxane bonds, exhibiting higher heat resistance temperatures. Even after high-temperature curing above 300°C, they still demonstrate excellent adhesion-enhancing performance. In contrast, the silane coupling agents used in Comparative Examples 1-3 are easily decomposed during high-temperature curing, essentially losing their adhesion-enhancing effect. Compared with Examples 7-25, Comparative Examples 1-3 exhibited some thermal decomposition during the curing process. Although this partially enhanced adhesion, the adhesion decreased after PCT treatment due to the inability to withstand the erosion of high-temperature steam. In contrast, the silane coupling agent provided by this invention showed excellent adhesion enhancement under the humid and hot environment of PCT high-temperature steam, resulting in excellent reliability of the photoresist film containing it.

[0196] The applicant declares that the present invention is illustrated by the above embodiments to provide a silane coupling agent and its application, as well as a photosensitive resin composition containing the same. However, the present invention is not limited to the above embodiments, i.e., it does not mean that the present invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, and selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A photosensitive resin composition, characterized in that, The photosensitive resin composition includes an alkali-soluble resin, a photosensitive compound, and a silane coupling agent; The alkali-soluble resin includes any one or a combination of at least two of the following: polyimide precursor resin, polyamic acid-polyimide copolymer, polyisoimide-polyamic acid copolymer, polyisoimide, or polyimide; The photosensitive compound is a compound containing a diazonoquinone group; The silane coupling agent has the structure shown in Formula I: Equation I; R1, R2, and R3 are each independently selected from any one of C1-C10 straight-chain or branched alkyl groups; R4 is selected from any of the following structures: ； In this context, * represents the linking site of a functional group.

2. The photosensitive resin composition according to claim 1, characterized in that, R1, R2, and R3 are each independently selected from any one of C1-C6 straight-chain or branched alkyl groups.

3. The photosensitive resin composition according to claim 1, characterized in that, The alkali-soluble resin comprises at least one of the structural units shown in Formula II, Formula III, or Formula IV: Formula II; Formula III; Formula IV; Among them, R 10 R 12 R 14 R 16 Each can independently represent a C4-C60 tetravalent organic group; R 11 R 13 R 15 R 17 Each independently represents a C3-C60 divalent organic group; R 18 R 19 Each is independently selected from any one of C1-C10 straight-chain or branched alkyl groups.

4. The photosensitive resin composition according to claim 3, characterized in that, The R 10 R 12 R 14 R 16 Each is independently selected from any one of substituted or unsubstituted C6-C30 tetravalent aromatic groups or substituted or unsubstituted C4-C20 tetravalent alicyclic groups; R 10 R 12 R 14 R 16 The substituents described herein are each independently selected from at least one of halogen, hydroxyl, unsubstituted or halogenated C1-C20 straight-chain or branched alkyl, and unsubstituted or halogenated C1-C20 alkoxy.

5. The photosensitive resin composition according to claim 4, characterized in that, The R 10 R 12 R 14 R 16 Each group is independently selected from any one of the following groups: in, The linking site of the representative group; R 21 R 22 R 23 R 24 R 25 R 26 Each is independently selected from any one of hydrogen, halogen, hydroxyl, unsubstituted or halogenated C1-C20 straight-chain or branched alkyl, unsubstituted or halogenated C1-C20 alkoxy; L 21 Selected from single bonds, -O-, -S-, sulfones, sulfones, unsubstituted or R'-substituted C1-C10 straight-chain or branched alkylene groups, unsubstituted or R'-substituted C6-C20 arylenes, Any one of them; L 22 L 23 Each is independently selected from any one of -O-, -S-, sulfone, sulfoxide, unsubstituted or R'-substituted C1-C10 straight-chain or branched alkylene groups; Ar 21 Selected from any one of the unsubstituted or R'-substituted C6-C20 arylene groups; R' is selected from at least one of halogen, hydroxyl, unsubstituted or halogenated C1-C20 straight-chain or branched alkyl, and unsubstituted or halogenated C1-C20 alkoxy.

6. The photosensitive resin composition according to claim 5, characterized in that, The R 10 R 12 R 14 R 16 Each group is independently selected from any one of the following groups: in, The linking site of the representative group.

7. The photosensitive resin composition according to claim 3, characterized in that, The R 11 R 13 R 15 R 17 Each group is independently selected from any one of the groups shown in Formula V, substituted or unsubstituted C6-C30 divalent aromatic groups, or substituted or unsubstituted C4-C20 divalent alicyclic groups; R 11 R 13 R 15 R 17 The substituents described herein are each independently selected from at least one of halogen, hydroxyl, unsubstituted or halogenated C1-C20 straight-chain or branched alkyl, and unsubstituted or halogenated C1-C20 alkoxy. Formula V; The linking site of the representative group; A is selected from any one of the following: single bond, -O-, -S-, sulfone group, substituted or unsubstituted C1-C10 divalent aliphatic hydrocarbon group, substituted or unsubstituted C3-C20 divalent alicyclic group, and substituted or unsubstituted C6-C30 divalent aromatic group; The substituents described in A are each independently selected from at least one of halogens, unsubstituted or halogenated C1-C10 straight-chain or branched alkyl groups, unsubstituted or halogenated C6-C30 aryl groups, and unsubstituted or halogenated C6-C30 phenolic groups. R 31 R 32 Each is independently selected from any one of halogen, nitro, cyano, carboxyl, unsubstituted or halogenated C1-C10 straight-chain or branched alkyl, unsubstituted or halogenated C1-C10 alkoxy, unsubstituted or halogenated C6-C30 aryl, amide, benzyl ether or benzyl alcohol. R 33 R 34 Each is independently selected from any one of C1-C10 straight-chain or branched alkylene groups, C1-C10 alkeneoxy groups, and C1-C10 groups containing divalent Si groups; R 35 R 36 Each independently selected m is an integer between 0 and 8; R 37 R 38 Each group is independently selected from any one of halogen, hydroxyl, nitro, cyano, carboxyl, unsubstituted or halogenated C1-C10 straight-chain or branched alkyl, unsubstituted or halogenated C1-C10 alkoxy, unsubstituted or halogenated C6-C30 aryl, C1-C10 ester or amide groups; k1, k2, s1, s2, p1, p2, q1, and q2 are each independently selected from integers between 0 and 4; n1 and n2 are each independently 0 or 1.

8. The photosensitive resin composition according to claim 7, characterized in that, In Formula V, A is selected from any one of sulfone, substituted or unsubstituted C1-C6 straight-chain or branched alkylene groups; The substituents described in A are each independently selected from at least one of halogens, phenolic groups, unsubstituted or halogenated C1-C6 straight-chain or branched alkyl groups.

9. The photosensitive resin composition according to claim 7, characterized in that, R in formula V 33 R 34 Each is independently selected from any one of C1-C6 straight-chain or branched alkylene groups and C1-C6 alkene oxides.

10. The photosensitive resin composition according to claim 7, characterized in that, R in formula V 35 R 36 Each independently or .

11. The photosensitive resin composition according to claim 7, characterized in that, In Equation V, p1, p2, q1, and q2 are each independently selected from integers from 1 to 3.

12. The photosensitive resin composition according to claim 7, characterized in that, The group represented by formula V has any one of the following structures: ； in, The linking site of the representative group.

13. The photosensitive resin composition according to claim 7, characterized in that, The R 11 R 13 R 15 R 17 Each is independently selected from the groups shown in Formula V. , or Any one of them; in, The linking site of the representative group; R 41 R 42 Each is independently selected from any one of halogen, hydroxyl, unsubstituted or halogenated C1-C20 straight-chain or branched alkyl, unsubstituted or halogenated C1-C20 alkoxy; L 41 Selected from single bonds, -O-, -S-, sulfones, sulfoxides, unsubstituted or halogenated C1-C10 straight-chain or branched alkylene groups, and unsubstituted or halogenated C6-C20 arylenes. Any one of them; L 42 L 43 Each is independently selected from any one of -O-, -S-, sulfone, sulfoxide, unsubstituted or halogenated C1-C10 straight-chain or branched alkylene groups; Ar 41 Selected from any one of the unsubstituted or R''-substituted C6-C20 arylene groups; R'' is selected from any one of halogen, hydroxyl, unsubstituted or halogen-substituted C1-C10 straight-chain or branched alkyl, and unsubstituted or halogen-substituted C1-C10 alkoxy. u1 and u2 are each independently selected from integers between 0 and 4.

14. The photosensitive resin composition according to claim 13, characterized in that, The R 11 R 13 R 15 R 17 Each is independently selected from the groups shown in Formula V. , or Any one of them; The linking site of the representative group.

15. The photosensitive resin composition according to claim 1, characterized in that, The weight-average molecular weight of the alkali-soluble resin is 2000-100000.

16. The photosensitive resin composition according to claim 15, characterized in that, The weight-average molecular weight of the alkali-soluble resin is 5000-50000.

17. The photosensitive resin composition according to claim 1, characterized in that, The photosensitive resin composition also includes a crosslinking agent.

18. The photosensitive resin composition according to claim 1, characterized in that, The photosensitive resin composition also includes solvents and / or other additives.

19. The photosensitive resin composition according to claim 18, characterized in that, The other additives include other silane coupling agents and / or surfactants.

20. The photosensitive resin composition according to claim 19, characterized in that, The other silane coupling agents include at least one of vinyl, allyl, oxocyclic, styryl, acyloxy, acryloyloxy, urea, amino, imidazole, tertiary amine, secondary amine, mercapto, or isocyanate groups.

21. The photosensitive resin composition according to claim 1, characterized in that, The photosensitive resin composition comprises the following components in weight percentage: Alkali-soluble resin 4-30%, Photosensitive compound 0.4-8%, The silane coupling agent is 0.001-0.5%. Crosslinking agent 0.4-10%, Other additives: 0.001-0.5% Solvent 55-95%.

22. The use of the photosensitive resin composition as described in claim 1 in a flat panel display device or a semiconductor device.

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