Photosensitive resin composition and application thereof

Abstract

The invention provides a photosensitive resin composition and application thereof. The photosensitive resin composition comprises alkali-soluble resin, a photosensitive compound, a first cross-linking agent and a second cross-linking agent. Through the design of the first cross-linking agent and the mutual compounding of the first cross-linking agent, the second cross-linking agent, the alkali-soluble resin and other components, aromatic formate groups in the first cross-linking agent react with hydroxyl groups in a resin system, so that a rich cross-linked network structure can be formed after high-temperature curing, the hydroxyl group content is reduced, and the curing time is shortened; the moisture absorption rate of the obtained photoresist curing film is remarkably reduced, the heat resistance, chemical corrosion resistance, water vapor corrosion resistance, mechanical strength and other properties of the photoresist curing film are effectively improved, and then the reliability of a device is improved.

Description

Technical Field

[0001] The present invention belongs to the field of lithography technology, and particularly relates to a photosensitive resin composition and its application. Background Art

[0002] With the continuous progress of electronic information technology, devices such as semiconductors and display panels are developing towards miniaturization, thinning, flexibility, and precision. Improving the reliability of devices is an urgent task in the current industrial community. The reliability of packaging is a key factor affecting the reliability of devices. Therefore, higher and higher requirements are put forward for the packaging technology and process of products. Generally speaking, due to its good heat resistance and high strength, polyimide materials are one of the mainstream material systems for advanced packaging at present and are widely used in the packaging field of electronic devices such as semiconductors. Specifically, for example, the RDL (redistribution layer), Bump layer, anti-radiation protection of devices, and insulating layer in IC devices, and the pixel definition layer (PDL), planarization layer (PLN), etc. in OLED devices. In order to obtain a high exposure sensitivity, that is, a high dissolution rate in an alkaline developer, alkali-soluble groups such as phenolic hydroxyl groups are usually introduced into the molecular repeating units of polyimide. However, this will result in a high hydroxyl residue in the photoresist cured film, which is likely to cause a high moisture absorption rate of the photoresist cured film, and thus pixel shrinkage, stress cracking, etc. will occur due to the release of water vapor during the manufacturing process and subsequent long-term use, affecting the long-term reliability of the product. In addition, the existing polyimide materials still have deficiencies in heat resistance and chemical resistance, which limits the application of photoresist cured films in electronic devices with high packaging technology levels.

[0003] Therefore, there is an urgent need in the art to develop a photoresist material with a low moisture absorption rate, good heat resistance and chemical resistance to improve the packaging reliability of devices. Summary of the Invention

[0004] Aiming at the deficiencies of the prior art, the purpose of the present invention is to provide a photosensitive resin composition and its application. Through the design of a first cross-linking agent with a specific structure and its mutual compounding with other components, the photosensitive resin composition can form a cured film with high mechanical strength, high barrier property, low moisture absorption rate, excellent heat resistance and chemical resistance after curing, effectively improving the reliability of devices.

[0005] To achieve this purpose, the present invention adopts the following technical solutions:

[0006] In the first aspect, the present invention provides a photosensitive resin composition, which includes a combination of an alkali-soluble resin, a photosensitive compound, a first cross-linking agent, and a second cross-linking agent; the first cross-linking agent has a structure shown in Formula I, and the second cross-linking agent has a structure shown in Formula II;

[0007]

[0008] Among them, X and Y each independently represent a C6-C60 aromatic group.

[0009] R1 is selected from any one of C1-C20 linear or branched alkyl groups and C6-C20 aryl groups.

[0010] R2 is selected from any one of H and C1-C8 linear or branched alkyl groups.

[0011] In formula I, m represents the number of -COOR1, which is an integer ≥ 1, that is, from 1 to the maximum number of substituents, for example, it can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, etc.; when m ≥ 2, multiple -COOR1 are the same or different groups. k represents the number of hydroxyl groups, which is an integer ≥ 0, that is, from 0 to the maximum number of substituents, for example, it can be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, etc.; n represents the number of carboxyl groups, n is an integer ≥ 0, that is, from 0 to the maximum number of substituents, for example, it can be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, etc.

[0012] In formula II, p represents the number of -CH2-OR2, which is an integer ≥ 1, that is, from 1 to the maximum number of substituents, for example, it can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, etc.; when m ≥ 2, multiple R2 are the same or different groups. q represents the number of hydroxyl groups, which is an integer ≥ 1, that is, from 1 to the maximum number of substituents, for example, it can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, etc.

[0013] In formula I, -COOR1 and optionally -COOH are both directly connected to the aromatic ring by a single bond; that is, -COOR1 is directly connected to the aromatic ring by a single bond, and when -COOH (n ≥ 1) exists in formula I, it is directly connected to the aromatic ring by a single bond.

[0014] The photosensitive resin composition provided by the present invention contains a combination of a first crosslinking agent and a second crosslinking agent. The first crosslinking agent contains an aromatic carboxylate group (-COOR1, which is directly connected to the aromatic ring by a single bond, i.e., an aromatic carboxylate group; when the aromatic ring is a benzene ring, it is a benzoate group). During the high-temperature curing process, the aromatic carboxylate group reacts with the hydroxyl groups in the photosensitive resin composition (such as alkali-soluble resin, second crosslinking agent, etc.). At the same time, the first crosslinking agent contains optionally hydroxyl groups and / or carboxyl groups, making it have good alkali solubility and capable of undergoing crosslinking reactions with reactive groups (such as aromatic carboxylate groups, carboxyl groups, hydroxyl groups) in the resin system. Based on the foregoing reactions, on the one hand, the photosensitive resin composition is cured to form a crosslinked structure, improving the heat resistance, chemical corrosion resistance, water vapor corrosion resistance, mechanical strength and other properties of the photoresist cured film. On the other hand, the hydroxyl group content in the composition is reduced, significantly reducing the moisture absorption rate of the obtained photoresist cured film, thereby improving the reliability of the device. The second crosslinking agent contains a benzyl ether / benzyl alcohol group (-CH2-OR2) and a hydroxyl group, has good alkali solubility, and is capable of undergoing crosslinking reactions with other components in the composition system during the high-temperature curing process, forming a crosslinked structure with acid and alkali resistance and high temperature resistance, thereby improving the corrosion resistance, high temperature stability, mechanical strength and other performance indicators of the photoresist / photoresist cured film. Through the design of the first crosslinking agent and its mutual compounding with components such as the second crosslinking agent and alkali-soluble resin, the present invention enables the photosensitive resin composition to form a rich crosslinked network structure after high-temperature curing, reduces the hydroxyl group content, forms a hydrophobic structure, significantly reduces the moisture absorption rate of the obtained photoresist cured film, effectively improves the heat resistance, chemical corrosion resistance, water vapor corrosion resistance, mechanical strength and other properties of the photoresist cured film, and has a high adhesion between the film and the substrate, thereby enhancing the reliability of the device.

[0015] The following are the preferred technical solutions of the present invention, but do not limit the technical solutions provided by the present invention. Through the following preferred technical solutions, the objectives and beneficial effects of the present invention can be better achieved and realized.

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

[0017] In the present invention, the expression "Ca-Cb" represents that the group has a carbon atom number of a - b; generally, unless otherwise specified, the carbon atom number does not include the carbon atom number of the substituent.

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

[0019] In the present invention, the expression of the ring structure crossed by "-" indicates that the bonding site is at any position on the ring structure where bonding can occur.

[0020] In the present invention, both "-*" and "*" represent the bonding sites of groups.

[0021] In the present invention, the term "C6-C60 aromatic group" may be an aromatic group such as C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56 or C58, etc., including aryl groups (such as phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, anthracenyl, phenanthryl, triphenylene, tetraphenyl, etc.) or aryl groups connected by bridging bonds (single bonds, O, S, sulfoxide groups, sulfone groups, substituted or unsubstituted alkylene groups, etc.).

[0022] The C1-C20 straight-chain or branched-chain alkyl group may be a straight-chain or branched-chain alkyl group such as C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc., and is exemplarily including but not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, 2-methylbutyl, n-pentyl, isopentyl, neopentyl, n-hexyl, neohexyl, 2-ethylhexyl, n-octyl, n-heptyl, n-nonyl, n-decyl, etc.

[0023] The C6-C20 aryl group may be an aryl group such as C6, C9, C10, C12, C14, C16, C18, etc., including monocyclic aryl groups and polycyclic aryl groups, and is exemplarily including but not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, indenyl, fluoranthenyl, fluorenyl and its derivatives, etc.

[0024] The C1-C8 straight-chain or branched-chain alkyl group may be a straight-chain or branched-chain alkyl group such as C2, C3, C4, C5, C6, C7, etc.

[0025] Preferably, m is an integer ≥2, and more preferably an integer ≥4.

[0026] Preferably, in formula I, n + k ≥ 1, that is, the first crosslinking agent contains at least 1 -COOR1 and also contains at least one of a hydroxyl group and a carboxyl group.

[0027] Preferably, n and k are each independently an integer from 0 to 4, and n + k ≥ 1.

[0028] Preferably, n is an integer from 1 to 4, and / or k is an integer from 0 to 4.

[0029] Preferably, 0 < m / (n + m) ≤ 1, and m / (n + m) is 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, or 1, etc. More preferably, 0.5 < m / (n + m) ≤ 0.95, and even more preferably, 0.6 < m / (n + m) ≤ 0.9.

[0030] Preferably, the first crosslinking agent has a structure shown in Formula IA:

[0031]

[0032] In Formula I and Formula IA, each R1 is independently selected from any one of C1-C20 linear or branched alkyl groups and C6-C20 aryl groups, preferably any one of C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkyl groups, and more preferably any one of C1-C6 linear or branched alkyl groups, and even more preferably methyl.

[0033] In Formula IA, X1 and X2 are each independently selected from a single bond, -O-, -S-, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkylene groups, substituted or unsubstituted silylene groups, or any one of the groups in which one or at least two non-connected -CH2- in the C1-C10 linear or branched alkylene groups are replaced by -O-, -S-, C6-C20 (such as C6, C9, C10, C12, C14, C16, C18, etc.) arylene groups.

[0034] The substituents of the substituted X1 and X2, R X1 are each independently selected from a hydroxyl group, a carboxyl group, -COOR A1 , unsubstituted or R'-substituted C6-C20 (such as C6, C9, C10, C12, C14, C16, C18, etc.) aryl groups, unsubstituted or R'-substituted C6-C20 (such as C6, C9, C10, C12, C14, C16, C18, etc.) aryloxy groups, or any one or at least two combinations thereof.

[0035] Each R' is independently selected from a hydroxyl group, a carboxyl group, or -COOR A2 or any one or at least two combinations thereof.

[0036] R A1 、R A2each independently selected from C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkyl groups;

[0037] In formula IA, m1 and m2 respectively represent the number of -COOR1, each independently selected from integers of 0-5, for example, they can be 0, 1, 2, 3, 4, or 5; n1 and n2 respectively represent the number of carboxyl groups, each independently selected from integers of 0-5, for example, they can be 0, 1, 2, 3, 4, or 5; k1 and k2 respectively represent the number of hydroxyl groups, each independently selected from integers of 0-5, for example, they can be 0, 1, 2, 3, 4, or 5.

[0038] In formula IA, m1 + m2 ≥ 1, so that the molecular structure contains at least 1 benzoate group; n1 + n2 + k1 + k2 ≥ 1, so that the molecular structure contains at least 1 hydroxyl group and / or carboxyl group.

[0039] In formula IA, s1 represents the number of, which is an integer of 0-4, for example, it can be 0, 1, 2, 3, or 4; when s1 ≥ 2, multiple X2 are the same or different, and multiple are the same or different.

[0040] In formula IA, s2 represents the number of substituent R X1 , which is an integer of 0-4, for example, it can be 0, 1, 2, 3, or 4; when s2 ≥ 2, multiple R X1 are the same or different groups.

[0041] Preferably, in formula IA, X1 and X2 each independently selected from a single bond, a substituted or unsubstituted C1-C10 linear or branched alkylene group, a substituted or unsubstituted silylene group, or any one of the groups in which one or at least two non-connected -CH2- in the C1-C10 linear or branched alkylene group are replaced by -O-.

[0042] Preferably, the substituents of X1 and X2 each independently selected from a hydroxyl group, a carboxyl group, -COOR A1 , an unsubstituted or R'-substituted phenyl group, an unsubstituted or R'-substituted phenoxy group, or any one or a combination of at least two of them; R' each independently selected from a hydroxyl group, a carboxyl group, or -COOR A2 or any one or a combination of at least two of them.

[0043] Preferably, X1 and X2 each independently selected from a single bond,

[0044]

[0045]

[0046] Represents the connection site of the group.

[0047] Preferably, the R X1 are each independently selected from any one or a combination of at least two of hydroxyl, carboxyl, -COOR A1 , unsubstituted or R'-substituted phenyl, and unsubstituted or R'-substituted phenoxy. More preferably, they are hydroxyl, carboxyl, -COOR A1 ,

[0048] any one of; Represents the connection site of the group.

[0049] Preferably, the first crosslinking agent is selected from any one or a combination of at least two of the following compounds:

[0050] wherein, R B are each independently selected from hydrogen or methyl, and at least one R B in a compound is methyl.

[0051] More preferably, the first crosslinking agent is selected from any one or a combination of at least two of the following compounds:

[0052]

[0053]

[0054] Preferably, the molecular weight of the first crosslinking agent is 200 - 2000, for example, it can be 300, 400, 500, 600, 700, 800, 900, 1000, 1100, 1200, 1300, 1400, 1500, 1600, 1700, 1800 or 1900, etc. More preferably, it is 300 - 1000.

[0055] Preferably, based on 100 parts by mass of the alkali-soluble resin, the mass of the first crosslinking agent is 0.1 - 40 parts, for example, it can be 0.2 parts, 0.5 parts, 0.8 parts, 1 part, 3 parts, 5 parts, 8 parts, 10 parts, 12 parts, 15 parts, 18 parts, 20 parts, 22 parts, 25 parts, 28 parts, 30 parts, 32 parts, 35 parts or 38 parts, etc. More preferably, it is 0.5 - 30 parts, and even more preferably, it is 1 - 25 parts.

[0056] Preferably, the first crosslinking agent comprises a combination of a compound with k = 0 and a compound with k > 0.

[0057] As a preferred technical solution of the present invention, from the perspectives of improving the resolution of the photosensitive resin composition and the photoresist cured film, no residue remaining during pattern formation, and a relatively high hydroxyl reaction rate, the compound with k = 0 and the compound with k > 0 are compounded and used in combination.

[0058] Preferably, the second crosslinking agent has a structure shown in any one of Formula IIA, Formula IIB, and Formula IIC:

[0059]

[0060] In Formula II, Formula IIA, Formula IIB, and Formula IIC, R2 is selected from any one of H, C1-C8 (such as C1, C2, C3, C4, C5, C6, C7, C8) linear or branched alkyl groups, more preferably any one of H, C1-C4 linear or branched alkyl groups, and even more preferably methyl or ethyl.

[0061] In Formula IIA and Formula IIC, Y1 and Y3 are each independently selected from any one of a single bond, -O-, -S-, -CO-, and unsubstituted or halogen-substituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkylene groups.

[0062] In Formula IIB and Formula IIC, Y2 is selected from any one of unsubstituted or halogen-substituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkylene groups.

[0063] In the present invention, the halogen includes fluorine, chlorine, bromine, or iodine; the "halogen substitution" means that at least one hydrogen in the group is substituted by a halogen (fluorine, chlorine, bromine, or iodine), preferably fluorine substitution.

[0064] In Formula IIA, Formula IIB, and Formula IIC, p1, p2, p3, and p4 respectively represent the number of benzylic ether / benzylic alcohol groups (-CH2-OR2), and q1, q2, q3, and q4 respectively represent the number of hydroxyl groups.

[0065] p1, p2, p3, q1, q2, and q3 are each independently selected from integers from 0 to 5, for example, they can be 0, 1, 2, 3, 4, or 5.

[0066] In Formula IIC, p4 and q4 are each independently selected from integers from 0 to 4, for example, they can be 0, 1, 2, 3, or 4.

[0067] In Formula IIA, p1 + p2 ≥ 1, and q1 + q2 ≥ 1.

[0068] In Formula IIB, p1 + p2 + p3 ≥ 1, q1 + q2 + q3 ≥ 1.

[0069] In Formula IIC, p1 + p2 + p3 + p4 ≥ 1, q1 + q2 + q3 + q4 ≥ 1.

[0070] Preferably, each of Y1 and Y3 is independently selected from any one of a single bond, an unsubstituted or halogen-substituted C1-C6 straight-chain or branched-chain alkylene group, preferably a single bond, representing the connection site of the group.

[0071] Preferably, Y2 is selected from any one of an unsubstituted or halogen-substituted C1-C6 straight-chain or branched-chain sub-alkylene group, more preferably

[0072] Preferably, the second crosslinking agent is selected from any one or a combination of at least two of the following compounds:

[0073]

[0074]

[0075] Preferably, based on 100 parts by mass of the alkali-soluble resin, the mass of the second crosslinking agent is 0.1 - 40 parts, such as 0.2 parts, 0.5 parts, 0.8 parts, 1 part, 3 parts, 5 parts, 8 parts, 10 parts, 12 parts, 15 parts, 18 parts, 20 parts, 22 parts, 25 parts, 28 parts, 30 parts, 32 parts, 35 parts or 38 parts, etc., more preferably 0.5 - 30 parts, and even more preferably 1 - 25 parts.

[0076] Preferably, the alkali-soluble resin includes any one or a combination of at least two of polyimide, polyimide precursor resin, polyamic acid-polyimide copolymer, polyamic acid ester-polyimide copolymer, polyisoimide-polyamic acid copolymer, and polyisoimide.

[0077] Preferably, the polyimide precursor resin includes polyamic acid ester and / or polyamic acid.

[0078] Preferably, the alkali-soluble resin contains at least one of the structural units represented by Formula III, Formula IV or Formula V:

[0079]

[0080]

[0081] Among them, R3, R6, R8, R 11Each independently represents a tetravalent organic group having 4 to 60 carbon atoms (such as 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.).

[0082] R4, R7, R9, R 12 Each independently represents a divalent organic group having 3 to 60 carbon atoms (such as C4, 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.).

[0083] R5, R 10 Each independently is selected from any one of linear or branched alkyl groups having 1 to 10 carbon atoms (such as C2, C3, C4, C5, C6, C7, C8, or C9, etc.).

[0084] As a preferred technical solution of the present invention, the alkali-soluble resin includes any one or a combination of at least two of a polyimide precursor resin (polyamic acid and / or polyamic acid ester, preferably including the structural unit shown in Formula III), a polyamic acid-polyimide copolymer and / or a polyamic acid ester-polyimide copolymer (preferably including the structural unit shown in Formula IV), and a polyimide (preferably including the structural unit shown in Formula V).

[0085] Preferably, the number of the structural units shown in Formula III in the alkali-soluble resin is f, and the number of the structural units shown in Formula V is g. The f and g are each independently an 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.

[0086] Preferably, the structural unit shown in Formula IV in the alkali-soluble resin includes a polyimide fragment and a polyamic acid (polyamic acid ester) fragment The two fragments are connected by chemical bonds, and their numbers are each independently an 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.

[0087] Preferably, the R3, R6, R8, R 11Each is independently selected from any one of a substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) tetravalent aromatic group, and a 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 group.

[0088] R3, R6, R8, R 11 The substituted substituents are each independently selected from at least one of halogen, hydroxyl, unsubstituted or halogen-substituted C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) straight or branched alkyl, and unsubstituted or halogen-substituted C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) alkoxy;

[0089] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or with multiple substituents. When there are multiple substituents (at least 2), they may be the same or different substituents. When the same expressions are mentioned below, they have the same meaning. The selection range of the substituents involved in the alkali-soluble resin is as shown above and will not be repeated one by one.

[0090] In the alkali-soluble resin of the present 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, anthracenyl, phenanthrenyl, triphenylene, naphthylene, etc.), and also include aryl groups connected by bridging bonds (single bonds, O, S, sulfoxide groups, sulfone groups, substituted or unsubstituted alkylene groups, etc.). The following "C6-C30 divalent aromatic groups" have similar examples.

[0091] The C4-C20 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) tetravalent alicyclic group, "alicyclic group" means a non-aromatic saturated or unsaturated cyclic structure, including a monocyclic, bridged, spiro or condensed ring, etc., illustratively including but not limited to: cyclobutane, cyclopentane, cyclohexane, bicyclooctane, etc. The following "C4-C20 divalent alicyclic group" has similar examples.

[0092] The C1-C20 linear or branched alkyl groups can all be linear or branched alkyl groups such as C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18; exemplary ones include but are 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.

[0093] Specific examples of the C1-C20 (such as C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) alkoxy groups can be monovalent groups obtained by connecting an O to the examples of the above-mentioned linear or branched alkyl groups.

[0094] In the present invention, the halogen includes fluorine, chlorine, bromine or iodine; the "halogen substitution" means that at least 1 hydrogen in the group is substituted by a halogen (fluorine, chlorine, bromine or iodine), preferably fluorine substitution.

[0095] Preferably, the R3, R6, R8, R 11 each independently selected from any one of the following groups:

[0096]

[0097] represents the connection site of the group.

[0098] R 21 、R 22 、R 23 、R 24 、R 25 、R 26 each independently selected from hydrogen, halogen, hydroxyl, unsubstituted or halogen-substituted C1-C20 (such as C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) linear or branched alkyl groups, unsubstituted or halogen-substituted C1-C20 (such as C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) alkoxy groups, and further preferably hydrogen, fluorine, methyl, methoxy, perfluoromethyl or perfluoromethoxy.

[0099] L 21 is selected from a single bond, -O-, -S-, carbonyl sulfonyl sulfinyl An unsubstituted or R”-substituted (such as C2, C3, C4, C5, C6, C7, C8 or C9, etc.) straight-chain or branched-chain alkylene group, an unsubstituted or R’-substituted C6-C20 (such as C6, C9, C10, C12, C14, C16 or C18, etc.) arylene group, any one of

[0100] L 22 and L 23 each independently selected from any one of a single bond, -O-, -S-, a carbonyl group, a sulfone group, a sulfoxide group, an unsubstituted or R”-substituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8 or C9, etc.) straight-chain or branched-chain alkylene group.

[0101] Ar 21 selected from any one of unsubstituted or R”-substituted C6-C20 (such as C6, C9, C10, C12, C14, C16 or C18, etc.) arylene groups.

[0102] R” is selected from at least one of a halogen, a hydroxyl group, an unsubstituted or halogen-substituted C1-C20 (such as C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) straight-chain or branched-chain alkyl group, an unsubstituted or halogen-substituted C1-C20 (such as C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) alkoxy group.

[0103] Preferably, the L 21 is selected from any one of a single bond, -O-, -CH2-, any one of

[0104] Preferably, the R3, R6, R8, R 11 each independently selected from any one of the following groups:

[0105]

[0106] wherein, represents the connection site of the group.

[0107] Preferably, the R4, R7, R9, R 12Each independently selected from the group represented by formula VI, a substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) divalent aromatic group, a substituted or unsubstituted C4-C20 (such as C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) divalent alicyclic group.

[0108] R4, R7, R9, R 12 The substituents of the substituted groups described in are each independently selected from at least one of halogen, hydroxy, unsubstituted or halogen-substituted C1-C20 (such as C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) straight-chain or branched-chain alkyl groups, unsubstituted or halogen-substituted C1-C20 (such as C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) alkoxy groups.

[0109]

[0110] Represents the connection site of the group.

[0111] A is selected from any one of a single bond, -O-, -S-, carbonyl, sulfone group, a substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8 or C9, etc.) divalent aliphatic hydrocarbon group, a substituted or unsubstituted C3-C20 (such as C4, C5, C6, C7, C8, C9, C10, C12, C14, C15, C17 or C18, etc.) divalent alicyclic group, a substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) divalent aromatic group.

[0112] The substituents of the substituted groups in A are each independently selected from at least one of halogen, unsubstituted or halogen-substituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8 or C9, etc.) straight-chain or branched-chain alkyl groups, unsubstituted or halogen-substituted C6-C30 (such as C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) aryl groups, unsubstituted or halogen-substituted C6-C30 (such as C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) phenol groups.

[0113] R 31 and R 32 are each independently selected from halogen, nitro, cyano, carboxyl, unsubstituted or halogen-substituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8 or C9, etc.) straight-chain or branched alkyl, unsubstituted or halogen-substituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8 or C9, etc.) alkoxy, unsubstituted or halogen-substituted C6-C30 (such as C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) aryl, amide group, benzyloxy group or benzyl alcohol group.

[0114] R 33 and R 34 are each independently selected from C1-C10 (such as C2, C3, C4, C5, C6, C7, C8 or C9, etc.) straight-chain or branched alkylene, C1-C10 (such as C2, C3, C4, C5, C6, C7, C8 or C9, etc.) alkyleneoxy, C1-C10 (such as C2, C3, C4, C5, C6, C7, C8 or C9, etc.) divalent Si-containing group.

[0115] R 35 and R 36 are each independently selected from R 51 selected from any one of H, C1-C8 (such as C2, C3, C4, C5, C6, C7, etc.) straight-chain or branched alkyl.

[0116] R 37 and R 38 are each independently selected from halogen, hydroxyl, nitro, cyano, carboxyl, unsubstituted or halogen-substituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8 or C9, etc.) straight-chain or branched alkyl, unsubstituted or halogen-substituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8 or C9, etc.) alkoxy, unsubstituted or halogen-substituted C6-C30 (such as C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) aryl, C1-C10 (such as C2, C3, C4, C5, C6, C7, C8 or C9, etc.) ester group or amide group.

[0117] a1, a2, b1, b2, c1, c2, d1, d2 are each independently selected from integers of 0-4, for example, they can be 0, 1, 2, 3, 4.

[0118] t1 and t2 are each independently 0 or 1; when t1 and t2 are 0, it means that the benzene ring is directly connected to -CO- by a single bond.

[0119] Preferably, in formula VI, A is selected from any one of a sulfone group, a substituted or unsubstituted C1-C6 (such as C1, C2, C3, C4, C5 or C6) straight-chain or branched-chain alkylene group; the substituents of the substituted A are each independently selected from at least one of a halogen, a phenol group, an unsubstituted or halogen-substituted C1-C6 (such as C1, C2, C3, C4, C5 or C6) straight-chain or branched-chain alkyl group, and an unsubstituted or halogen-substituted C1-C6 (such as C1, C2, C3, C4, C5 or C6) alkoxy group.

[0120] More preferably, in formula VI, A is selected from a sulfone group,

[0121] Preferably, in formula VI, R 33 , R 34 are each independently selected from any one of a C1-C6 (such as C1, C2, C3, C4, C5 or C6) straight-chain or branched-chain alkylene group and a C1-C6 (such as C1, C2, C3, C4, C5 or C6) alkylene oxide group, and more preferably or

[0122] Preferably, in formula VI, R 35 , R 36 are each independently or

[0123] Preferably, in formula VI, a1, a2, b1, and b2 are each independently selected from integers from 1 to 3, and more preferably 1 or 2.

[0124] Preferably, the group represented by formula VI has any one of the following structures:

[0125]

[0126]

[0127] Wherein, represents the connection site of the group. Preferably, R4, R7, R9, R 12 are each independently selected from any one of the groups represented by formula VI, ; represents the connection site of the group.

[0128] R 41 , R 42Each independently selected from halogen, hydroxy, unsubstituted or halogen-substituted C1-C20 (such as C2, C3, C4, C5, C6, C7, C8, C9, C10, C12, C15 or C18, etc.) linear or branched alkyl, unsubstituted or halogen-substituted C1-C20 (such as C2, C3, C4, C5, C6, C7, C8, C9, C10, C12, C15 or C18, etc.) alkoxy, and further preferably hydroxy, fluorine, methyl, methoxy, perfluoromethyl or perfluoromethoxy.

[0129] L 41 Selected from a single bond, -O-, -S-, carbonyl, sulfone, sulfoxide, unsubstituted or halogen-substituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8 or C9, etc.) linear or branched alkylene, unsubstituted or halogen-substituted C6-C20 (such as C6, C9, C10, C12, C14, C16 or C18, etc.) arylene, Any one of them.

[0130] L 42 L 43 Each independently selected from a single bond, -O-, -S-, carbonyl, sulfone, sulfoxide, unsubstituted or halogen-substituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8 or C9, etc.) linear or branched alkylene.

[0131] Ar 41 Selected from any one of unsubstituted or R”'-substituted C6-C20 (such as C6, C9, C10, C12, C14, C16 or C18, etc.) arylene.

[0132] R”' is selected from halogen, hydroxy, unsubstituted or halogen-substituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8 or C9, etc.) linear or branched alkyl, unsubstituted or halogen-substituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8 or C9, etc.) alkoxy.

[0133] u1 and u2 each independently selected from integers from 0 to 4, for example, can be 0, 1, 2, 3 or 4.

[0134] Preferably, the L 41 Selected from a single bond, -O-, -CH2-, Any one of them.

[0135] Preferably, the R4, R7, R9, R 12 Each independently selected from the groups shown in Formula VI,

[0136] Any one of .

[0137] Preferably, the weight average molecular weight of the alkali-soluble resin is 2000-100000, for example, 3000, 5000, 8000, 10000, 15000, 20000, 25000, 30000, 35000, 40000, 45000, 50000, 55000, 60000, 70000, 80000 or 90000, and more preferably 5000-50000.

[0138] Preferably, the alkali-soluble resin comprises a polyimide precursor resin (polyamic acid and / or polyamic acid ester, preferably comprising a structural unit represented by formula III), which can be prepared by a method known in the art, illustratively comprising any one of the following routes: route (1) directly polymerizing a diamine with a dianhydride to obtain a polyamic acid, and then esterifying the polyamic acid ester; route (2) reacting a dianhydride with an alcohol to obtain a dicarboxylic acid diester, and then reacting the dianhydride with thionyl chloride to obtain a diacyl chloride diester, and then polymerizing the diamine compound to obtain a polyamic acid ester; route (3) reacting a dianhydride with an alcohol to obtain a dicarboxylic acid diester, and then reacting the diamine compound in the presence of a dehydrating agent such as cyclohexylcarbodiimide to obtain a polyamic acid ester.

[0139] Preferably, the preparation method of the polyimide precursor resin comprises: firstly, a diamine monomer (NH2-R4-NH2) and a dianhydride monomer The polyamic acid is polymerized to obtain polyamic acid; and the polyamic acid is subjected to esterification reaction to obtain the polyimide precursor resin.

[0140] Preferably, the reagents for the esterification reaction include N,N-dimethylformamide dimethyl acetal and / or N,N-dimethylformamide diethyl acetal.

[0141] Preferably, the polyimide precursor resin may introduce a capping agent at the end group, and in order to further improve the performance, the capping agent may introduce alkenyl, alkynyl, benzyl ether, benzyl alcohol and other groups, and improve the strength and other properties of the film through cross-linking reaction during the subsequent curing process.

[0142] Preferably, the capping agent illustratively includes but is not limited to:

[0143] Preferably, the photosensitive compound is a compound containing a diazonaphthoquinone group.

[0144] Preferably, the structure of the diazonaphthoquinone group is Represents the connection site of the representative group.

[0145] Preferably, the photosensitive resin composition further includes an auxiliary agent.

[0146] Preferably, the auxiliary agent includes any one or a combination of at least two of a silane coupling agent, a surfactant, and a curing accelerator.

[0147] In order to improve the processing and application performance of the photosensitive resin composition, auxiliary agents such as a surfactant (leveling agent), a silane coupling agent, and a curing accelerator (catalyst) can be added to improve the film thickness uniformity during the coating process of the photosensitive resin composition, the adhesion to the substrate, and the conversion rate of the curing reaction, thereby improving the flatness of the film, enhancing the adhesion between the photoresist cured film and the substrate, and reducing the residual film after development.

[0148] Preferably, the silane coupling agent includes a silane coupling agent containing an oxygen-containing heterocycle; in the curing process, the oxygen-containing heterocycle group can form stable molecular bonds with the crosslinking agent and the resin through ring-opening reaction, thereby enhancing the adhesion between the photoresist cured film and the substrate.

[0149] Preferably, by compounding different types of silane coupling agents, the adaptability of the photoresist cured film between different types of substrates can be improved, and a cured film with good bonding strength on different types of substrates can be obtained. The silane coupling agent includes at least one of an amino group, an epoxy group, an isocyanate group, an alkenyl group, an acryloyloxy group, a ureido group, and a mercapto group; exemplarily including but not limited to: 3-isocyanatopropyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 3-ureidopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, (3-glycidoxypropyl)triethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, N-(3-(trimethylsilyl)propyl)aniline, 3-(2,3-epoxypropoxy)propyltrimethoxysilane, and tridecafluorooctyltrimethoxysilane, any one or a combination of at least two of them.

[0150] Preferably, the surfactant includes any one or a combination of at least two of a fluorine-containing surfactant, a polyethylene glycol-containing surfactant, and a silicone-oxygen structure-containing surfactant, which can function as a leveling agent and can improve the flatness of the film and improve the film thickness deviation at the edge of the substrate.

[0151] Preferably, the curing accelerator includes any one or a combination of at least two of a photoacid generator, a thermal acid generator, a photobase generator, and a thermal base generator. Further preferably, it is a thermal acid generator and / or a thermal base generator, which can promote the curing crosslinking reaction between the alkali-soluble resin and the first crosslinking agent and the second crosslinking agent and / or the ring-closure reaction of the resin during the curing process.

[0152] From the perspective of environmental friendliness and improving the device manufacturing process, in order to reduce the manufacturing temperature of the device, the thermal acid generator and the thermal base generator should have a low thermal initial decomposition temperature; preferably, the thermal decomposition temperatures of the thermal acid generator and the thermal base generator are each independently 90 - 250 °C, more preferably 100 - 200 °C.

[0153] Preferably, the mass percentage content of the curing accelerator in the photosensitive resin composition is 0.005% - 10%, further preferably 0.02% - 3%, and more preferably 0.1% - 1%.

[0154] Preferably, the thermal acid generator includes compounds that generate strong acids, such as p-toluenesulfonic acid, benzenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, etc. Particularly preferably, the acid generator with a thermal decomposition temperature between 90 - 250 °C can be used in the form of salts (such as ammonium salts, sulfonium salts), or in the form of chemical bonds such as imide sulfonates.

[0155] Preferably, the thermal base generator includes substances that generate organic nitrogen-containing compounds as bases, specifically, it can be primary aliphatic amines, tertiary aliphatic amines, primary aromatic amines, tertiary aromatic amines, quaternary ammonium bases, imidazoles, amidines, quinolines, pyridines, piperidines, etc.; from the perspective of improving the device stability, compounds without halogens are preferred, and specific examples that can be cited include: guanidine p-toluenesulfonylacetate, guanidine benzenesulfonylacetate, guanidine phenylpropiolate, tert-butyl 9-anthrylmethyl piperidine-1-carboxylate, 9-anthrylmethyl N,N-diethylcarbamate, (E)-N-cyclohexyl-3-(2-hydroxyphenyl)acrylamide, (E)-1-piperidino-3-(2-hydroxyphenyl)-2-propen-1-one, methyl 9-anthrylmethyl N-cyclohexylcarbamate, guanidino 2-(3-benzoylphenyl)propionate, 1-(anthraquinon-2-yl)ethyl imidazole-1-carboxylate, tert-butyl (2-nitrophenyl)methyl-4-hydroxypiperidine-1-carboxylate, (2-nitrophenyl)methyl-4-(methacryloyloxy), 1-(anthraquinon-2-yl)ethyl N,N-dicyclohexylcarbamate, dicyclohexyl 2-(3-benzoylphenyl)propionate, cyclohexyl 2-(3-benzoylphenyl)propionate, 9-anthrylmethyl N,N-dicyclohexylcarbamate, 1-(anthraquinon-2-yl)ethyl N-cyclohexylcarbamate, etc.

[0156] Preferably, the photosensitive resin composition includes the following components by mass parts:

[0157]

[0158] Specifically, based on 100 parts by mass of the alkali-soluble resin, the mass of the photosensitive compound is 0.1 - 40 parts, for example, it can be 0.2 parts, 0.5 parts, 0.8 parts, 1 part, 3 parts, 5 parts, 8 parts, 10 parts, 12 parts, 15 parts, 18 parts, 20 parts, 22 parts, 25 parts, 28 parts, 30 parts, 32 parts, 35 parts or 38 parts, etc.

[0159] The mass of the first crosslinking agent is 0.1 - 40 parts, for example, it can be 0.2 parts, 0.5 parts, 0.8 parts, 1 part, 3 parts, 5 parts, 8 parts, 10 parts, 12 parts, 15 parts, 18 parts, 20 parts, 22 parts, 25 parts, 28 parts, 30 parts, 32 parts, 35 parts or 38 parts, etc.

[0160] The mass of the second crosslinking agent is 0.1 - 40 parts, for example, it can be 0.2 parts, 0.5 parts, 0.8 parts, 1 part, 3 parts, 5 parts, 8 parts, 10 parts, 12 parts, 15 parts, 18 parts, 20 parts, 22 parts, 25 parts, 28 parts, 30 parts, 32 parts, 35 parts or 38 parts, etc.

[0161] The mass of the additive is 0.001 - 10 parts, for example, it can be 0.002 parts, 0.005 parts, 0.008 parts, 0.01 parts, 0.03 parts, 0.05 parts, 0.08 parts, 0.1 parts, 0.3 parts, 0.5 parts, 0.8 parts, 1 part, 2 parts, 3 parts, 4 parts, 5 parts, 6 parts, 7 parts, 8 parts or 9 parts, etc.

[0162] Preferably, the photosensitive resin composition further includes a solvent.

[0163] Due to the requirements of storage stability and low volatility, the boiling point of the solvent under standard atmospheric pressure is usually higher than 90°C, and the baking temperature for removing the solvent in the lithography process is usually between 90 - 140°C.

[0164] Preferably, the solvent is a commonly used solvent 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, and N,N-dimethylacetamide.

[0165] Preferably, the amount of the solvent is such that the solid content of the photosensitive resin composition is 5 - 45 wt%, for example, it can be 8 wt%, 10 wt%, 12 wt%, 15 wt%, 18 wt%, 20 wt%, 22 wt%, 25 wt%, 28 wt%, 30 wt%, 32 wt%, 35 wt%, 38 wt%, 40 wt%, 42 wt% or 44 wt%, etc.

[0166] Preferably, the mass percentage content of the solvent in the photosensitive resin composition is 55-95%, so that the solid content is 5-45 wt%, more preferably 8-30 wt%. An excessively low solid content is not conducive to forming a continuous film with a certain thickness, while an excessively high solid content may lead to too high viscosity, and then cause problems such as air bubbles and poor flatness during the film coating process.

[0167] In a second aspect, the present invention provides a photo-resist cured film, which is prepared from the photosensitive resin composition as described in the first aspect.

[0168] In a third aspect, the present invention provides an application of the photosensitive resin composition as described in the first aspect and the photo-resist cured film as described in the second aspect in semiconductor devices or flat panel display devices.

[0169] Preferably, the photosensitive resin composition is used as a stress buffer material, a passivation layer, a pixel defining layer, a planarization layer, etc. in semiconductor devices.

[0170] Preferably, after the photosensitive resin composition is coated, pre-baked, lithographed, developed, and cured, a photo-resist cured film can be formed and permanently retained in semiconductor devices or flat panel display devices (display panels). The photo-resist cured film has excellent substrate adhesion and can be used in the encapsulation process of flexible semiconductors, flat panel displays and other devices.

[0171] Compared with the prior art, the present invention has the following beneficial effects:

[0172] In the photosensitive resin composition provided by the present invention, through the design of the first cross-linking agent and its mutual compounding with components such as the second cross-linking agent and the alkali-soluble resin, the aromatic formate group in the first cross-linking agent reacts with the hydroxyl group in the resin system, and a rich cross-linked network structure can be formed after high-temperature curing, reducing the hydroxyl group content, significantly reducing the moisture absorption rate of the obtained photo-resist cured film, with its water absorption rate < 0.5%, and effectively improving the heat resistance, chemical corrosion resistance, water vapor corrosion resistance, mechanical strength and other properties of the photo-resist cured film, thereby improving the reliability of the device. Detailed Embodiments

[0173] The technical solutions of the present invention will be further described below through specific embodiments. Those skilled in the art should understand that the embodiments are only for helping to understand the present invention and should not be regarded as specific limitations on the present invention.

[0174] In the present invention, the first cross-linking agent can be obtained through market channels or can be self-made by organic synthesis methods well-known in the art, such as hydrolyzing esters or esterifying carboxyl groups.

[0175] In a specific embodiment, the first cross-linking agent can be obtained from raw material A Obtained by the hydrolysis reaction of; the hydrolysis reaction is carried out under alkaline conditions.

[0176] In another specific embodiment, the first crosslinking agent can be obtained by the esterification reaction of raw material B Obtained by the esterification reaction of.

[0177] The following will take synthesis examples as an example to detail the specific preparation method of the first crosslinking agent of the present invention, but the preparation method of the first crosslinking agent is not limited to these synthesis examples.

[0178] Synthesis Example 1: Synthesis of Compound A1 R B Each independently selected from hydrogen or methyl, and at least one of the Rs B Is methyl.

[0179] Under nitrogen protection, 65.4 g of tetramethyl 5'-(3,5-bis(methoxycarbonyl)phenyl)-[1,1':3',1”-terphenyl]-3,3”,5,5”-tetracarboxylate (the structure is as follows, purchased from Puyang Huicheng Electronic Materials Co., Ltd.), 200 mL of toluene, and 0.5 g of anhydrous sodium hydroxide were put into a 500 mL three-necked flask, heated to 50 °C and stirred to completely dissolve the tetramethyl 5'-(3,5-bis(methoxycarbonyl)phenyl)-[1,1':3',1”-terphenyl]-3,3”,5,5”-tetracarboxylate; 1.2 g of deionized water was slowly added dropwise, and after reacting for 10 h under nitrogen protection, sodium hydroxide was filtered off, the filtrate was washed with a dilute hydrochloric acid solution with a pH of 5 until the pH value did not change, then washed with deionized water until neutral, the organic phase was separated, anhydrous magnesium sulfate was added and dried overnight, filtered and the filtrate was collected, distilled under reduced pressure and the solid was collected, and vacuum dried at 50 °C for 24 h to obtain Compound A1 (titrated with 0.1 mol / L sodium bicarbonate solution, the acid value was 55 mg KOH / g, indicating that part of the benzoate groups in the raw material were hydrolyzed to form carboxyl groups).

[0180]

[0181] Synthesis Example 2: Synthesis of Compound A2 R B Each independently selected from hydrogen or methyl, and at least one of the Rs B Is methyl.

[0182] Under nitrogen protection, 90.4 g of tetramethyl 5,5'-((2,2-bis((3,5-bis(methoxycarbonyl)phenoxy)methyl)propane-1,3-diyl)bis(oxo))diisophthalate (with the structure as follows, purchased from Puyang Huicheng Electronic Materials Co., Ltd.), 200 mL of toluene, and 0.5 g of anhydrous sodium hydroxide were added into a 500 mL three-necked flask. It was heated to 50 °C and stirred until tetramethyl 5,5'-((2,2-bis((3,5-bis(methoxycarbonyl)phenoxy)methyl)propane-1,3-diyl)bis(oxo))diisophthalate was completely dissolved; 1.5 g of deionized water was slowly added dropwise. After reacting for 10 h under nitrogen protection, sodium hydroxide was removed by filtration. The filtrate was washed with a dilute hydrochloric acid solution with a pH of 5 until the pH value did not change, and then washed with deionized water until neutral. The organic phase was separated, anhydrous magnesium sulfate was added and dried overnight, the filtrate was filtered and collected, and the solid was collected by vacuum distillation and vacuum dried at 50 °C for 24 h to obtain compound A2 (titrated with 0.1 mol / L sodium bicarbonate solution, acid value: 50 mg KOH / g).

[0183]

[0184] Synthesis Example 3: Synthesis of Compound A3 R B Each independently selected from hydrogen or methyl, and at least one of the Rs B is methyl.

[0185] Under nitrogen protection, 62.2 g of trimethyl 5,5',5”-(methylsilanetriyl)trimesate (with the structure as follows, purchased from Puyang Huicheng Electronic Materials Co., Ltd.), 200 mL of toluene, and 0.5 g of anhydrous sodium hydroxide were added into a 500 mL three-necked flask. It was heated to 50 °C and stirred until hexamethyl 5,5',5”-(methylsilanetriyl)triisophthalate was completely dissolved; 1 g of deionized water was slowly added dropwise. After reacting for 10 h under nitrogen protection, sodium hydroxide was removed by filtration. The filtrate was washed with a dilute hydrochloric acid solution with a pH of 5 until the pH value did not change, and then washed with deionized water until neutral. The organic phase was separated, anhydrous magnesium sulfate was added and dried overnight, the filtrate was filtered and collected, and the solid was collected by vacuum distillation and vacuum dried at 50 °C for 24 h to obtain compound A3 (titrated with 0.1 mol / L sodium bicarbonate solution, acid value: 51 mg KOH / g).

[0186]

[0187] Synthesis Example 4: Synthesis of Compound A4

[0188] Under nitrogen protection, 34.6 g of 4-hydroxy-[1,1'-biphenyl]-3,3',5,5'-tetracarboxylic acid (structure as follows) was put into a three-necked flask, and 150 mL of N-methylpyrrolidone was added. After stirring at room temperature until completely dissolved, the temperature was raised to 60 °C. 50 g of N,N-dimethylformamide dimethyl acetal was slowly added dropwise to the system. After reacting for 3 h, the temperature was lowered to room temperature. The reaction solution was poured into deionized water, and the precipitate was collected by filtration. After recrystallization with methanol, compound A4 was obtained.

[0189]

[0190] Synthesis Example 5: Synthesis of Compound A5 R B Each independently selected from hydrogen or methyl, and at least one of the Rs B is methyl.

[0191] Under nitrogen protection, 49.6 g of 4,4',4”,4”'-methanetetrayltetrabenzoic acid (structure as follows) was put into a three-necked flask, and 150 mL of N-methylpyrrolidone was added. After stirring at room temperature until completely dissolved, the temperature was raised to 60 °C. 40 g of N,N-dimethylformamide dimethyl acetal was slowly added dropwise to the system. After reacting for 3 h, the temperature was lowered to room temperature. The reaction solution was poured into deionized water, and the precipitate was collected by filtration. It was dried in vacuo at 50 °C for 24 h to obtain compound A5 (titrated with 0.1 mol / L sodium bicarbonate solution, acid value 112 mg KOH / g).

[0192]

[0193] In the following specific embodiments of the present invention, the weight-average molecular weight of the alkali-soluble resin was measured by gel permeation chromatography (GPC). The test instrument was a Viscotek gel permeation chromatograph from Malvern Instruments, with a D6000M chromatographic column.

[0194] Preparation Example 1: Preparation of Alkali-Soluble Resin 1

[0195] Alkali-soluble resin 1 (polyimide precursor resin), the preparation method is as follows: Under nitrogen protection, 6.04 g of diamine compound 1 was dissolved in 20 mL of N-methylpyrrolidone (NMP), and the temperature was lowered to 0 °C. A mixture of 3.87 g of 3,3,4,4-diphenylether tetracarboxylic dianhydride and 12 g of anhydrous NMP was quickly added to the reaction system, and the reaction was maintained at 0 °C for 5 h. The temperature was raised to 60 °C, and 2.68 g of N,N-dimethylformamide dimethyl acetal was slowly added dropwise to the reaction system, and the reaction was maintained at 60 °C for 2 h. The temperature was lowered to room temperature, and the reaction solution was poured into 300 mL of deionized water. The precipitate was collected by filtration, and the precipitate was dried in vacuo at 50 °C for 24 h to obtain alkali-soluble resin 1 (PI-1), with a weight-average molecular weight of 8500.

[0196]

[0197] Production Example 2: Preparation of alkali-soluble resin 2

[0198] Alkali-soluble resin 2 (polyimide precursor resin), the preparation method of which is only different from that of Production Example 1 in that diamine compound 1 is replaced with an equimolar amount of diamine compound 2, and other raw materials and process parameters are the same as those of Production Example 1, to obtain alkali-soluble resin 2 (PI-2) with a weight-average molecular weight of 8300.

[0199]

[0200] Production Example 3: Preparation of alkali-soluble resin 3

[0201] Alkali-soluble resin 3 (polyimide precursor resin), the preparation method is as follows: Dissolve 0.692 g of diamine compound 3 and 5.44 g of diamine compound 1 in 20 mL of NMP, cool down to 0 °C, and quickly add a mixture of 3.87 g of 3,3,4,4-diphenylether tetracarboxylic dianhydride and 12 g of NMP to the reaction system, and keep the reaction at 0 °C for 5 h. Heat up to 60 °C, slowly drop 2.68 g of N,N-dimethylformamide dimethyl acetal into the reaction system, and keep the reaction at 60 °C for 2 h. Cool down to room temperature, pour the reaction solution into 300 mL of deionized water, filter and collect the precipitate, and vacuum dry the precipitate at 50 °C for 24 h to obtain alkali-soluble resin 3 (PI-3) with a weight-average molecular weight of 8500.

[0202]

[0203] Production Example 4: Preparation of alkali-soluble resin 4

[0204] Alkali-soluble resin 4 (polyimide-polyamide acid ester copolymer), the preparation method is as follows: Under nitrogen protection, dissolve 6.04 g of diamine compound 1 in 20 mL of NMP, cool down to 0 °C, and quickly add a mixture of 3.87 g of 3,3,4,4-diphenylether tetracarboxylic dianhydride and 12 g of anhydrous NMP to the reaction system, and keep the reaction at 0 °C for 5 h. Heat up to 60 °C, slowly drop 2.0 g of N,N-dimethylformamide dimethyl acetal into the reaction system, and keep the reaction at 60 °C for 2 h. Cool down to room temperature, pour the reaction solution into 300 mL of deionized water, filter and collect the precipitate, and vacuum dry the precipitate at 50 °C for 24 h. Then dissolve the resin intermediate product in 20 mL of NMP, add 0.255 g of acetic anhydride to the system and react at room temperature for 5 h. Pour the reaction solution into 300 mL of deionized water, filter and collect the precipitate, and vacuum dry the precipitate at 50 °C for 24 h to obtain an alkali-soluble resin (PI-4) copolymerized with polyimide-polyamide acid ester with a weight-average molecular weight of 8500.

[0205] Preparation Example 5: Preparation of alkali-soluble resin 5

[0206] Alkali-soluble resin 5 (polyimide precursor resin) was prepared as follows: Under nitrogen protection, 2.75 g of 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane and 2.5 g of 4,4'-diaminodiphenyl ether were dissolved in 20 mL of NMP. The temperature was lowered to 0 °C, and a mixture of 7.75 g of 3,3,4,4-diphenylethertetracarboxylic dianhydride and 22 g of anhydrous NMP was quickly added to the reaction system. The reaction was maintained at 0 °C for 5 h. The temperature was raised to 60 °C, and 6.6 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 temperature was lowered to room temperature, and the reaction solution was poured into 300 mL of deionized water. The precipitate was collected by filtration, and the precipitate was dried in vacuo at 50 °C for 24 h to obtain polyimide precursor 5 (PI-5) with a weight average molecular weight of 5500.

[0207] Preparation Example 6: Preparation of alkali-soluble resin 6

[0208] Alkali-soluble resin 6 (polyimide precursor resin) differed from Preparation Example 2 only in that 3,3,4,4-diphenylethertetracarboxylic dianhydride was replaced with an equimolar amount of 4,4'-(hexafluoroisopropylidene)diphthalic anhydride. All other raw materials and process parameters were the same as those in Preparation Example 2, and alkali-soluble resin 6 (PI-6) was obtained with a weight average molecular weight of 8800.

[0209] Example 1

[0210] A photosensitive resin composition, comprising the following components by mass: 100 parts of alkali-soluble resin 1 (Preparation Example 1, PI-1), 20 parts of a photosensitive compound, 5 parts of first crosslinking agent A1 (Synthesis Example 1), 5 parts of first crosslinking agent A4 (Synthesis Example 4), 10 parts of second crosslinking agent B, 1 part of thermal acid generator 4-nitrobenzyl-3-(trifluoromethyl)benzenesulfonate, 1 part of a fluorine-containing surfactant, 1 part of silane coupling agent 1 Shin-Etsu Chemical KBM403, and 850 parts of γ-butyrolactone.

[0211] Among them, the photosensitive compound is Q is The second crosslinking agent B is

[0212] The preparation method of the photosensitive resin composition is as follows: All components were mixed and dissolved uniformly according to the formulation amounts to obtain the photosensitive resin composition.

[0213] Examples 2 - 6

[0214] A photosensitive resin composition, which is different from Example 1 only in that the alkali-soluble resin is replaced with an equal mass of alkali-soluble resins PI-2 to PI-6, and other components and dosages (items not listed in Table 1) are the same as those in Example 1.

[0215] Examples 7-8

[0216] A photosensitive resin composition, which is different from Example 1 only in that the first crosslinking agent A1 is replaced with an equal mass of crosslinking agents A2 and A3, and other components and dosages (items not listed in Table 1) are the same as those in Example 1.

[0217] Example 9

[0218] A photosensitive resin composition includes the following components in parts by mass: 100 parts of alkali-soluble resin 1 (Preparation Example 1, PI-1), 20 parts of photosensitive compound, 10 parts of first crosslinking agent A1, 10 parts of second crosslinking agent B, 1 part of thermal acid generator 4-nitrobenzyl-3-(trifluoromethyl)benzenesulfonate, 1 part of fluorine-containing surfactant, 1 part of silane coupling agent KBM403, and 850 parts of γ-butyrolactone.

[0219] Examples 10-14

[0220] A photosensitive resin composition, which is different from Example 9 only in that the alkali-soluble resin is replaced with an equal mass of alkali-soluble resins PI-2 to PI-6, and other components and dosages (items not listed in Table 1) are the same as those in Example 9.

[0221] Example 15

[0222] A photosensitive resin composition includes the following components in parts by mass: 100 parts of alkali-soluble resin 1 (Preparation Example 1, PI-1), 20 parts of photosensitive compound, 2 parts of first crosslinking agent A5, 8 parts of first crosslinking agent A4, 10 parts of second crosslinking agent B, 1 part of thermal acid generator 4-nitrobenzyl 3-(trifluoromethyl)benzenesulfonate, 1 part of fluorine-containing surfactant, 1 part of silane coupling agent KBM403, and 850 parts of γ-butyrolactone.

[0223] Comparative Example 1

[0224] A photosensitive resin composition includes the following components in parts by mass: 100 parts of alkali-soluble resin 1 (Preparation Example 1, PI-1), 20 parts of photosensitive compound, 10 parts of second crosslinking agent B, 1 part of fluorine-containing surfactant, 1 part of silane coupling agent KBM403, and 850 parts of γ-butyrolactone.

[0225] Comparative Examples 2-6

[0226] A photosensitive resin composition, which is different from Comparative Example 1 only in that the alkali-soluble resin is replaced with an equal mass of alkali-soluble resins PI-2 to PI-6, and other components and dosages (items not listed in Table 1) are the same as those in Comparative Example 1.

[0227] Comparative Example 7

[0228] A photosensitive resin composition, which is different from Comparative Example 1 only in that the dosage of the second crosslinking agent B becomes 15 parts, and other components and dosages (items not listed in Table 1) are the same as those in Comparative Example 1.

[0229] Comparative Example 8

[0230] A photosensitive resin composition, which is different from Comparative Example 1 only in that the dosage of the second crosslinking agent B becomes 20 parts, and other components and dosages (items not listed in Table 1) are the same as those in Comparative Example 1.

[0231] The specific components are shown in Table 1.

[0232] Table 1

[0233]

[0234] In Table 1, "--" represents that the component is not added; the first crosslinking agents A1, A2, A3, A4, and A5 are respectively from Synthesis Examples 1-5.

[0235] The performance tests of the aforementioned photosensitive resin composition are as follows:

[0236] (1) Water absorption test

[0237] The photosensitive resin composition to be tested is coated on a 4-inch square glass substrate by spin coating, pre-baked at 120 °C for 180 s to remove most of the solvent, and a film of about 10 μm is formed. It is exposed without a mask under an ultraviolet exposure machine to promote the decomposition of the photosensitive compound, and then the coated glass substrate is placed in a clean oven at 250 °C under nitrogen protection (oxygen concentration < 20 ppm) and cured for 60 min. The coated glass substrate is soaked in a 5% HF aqueous solution and the film is peeled off from the glass substrate. After the film is washed with deionized water, it is placed in a clean oven at 200 °C under nitrogen protection (oxygen concentration < 20 ppm) and cured for 30 min. After the cured film is treated in a constant temperature and humidity chamber at 80 °C and 80% relative humidity for 24 h, about 10 mg of the sample is accurately weighed, and the weight loss relative to the initial weight is measured by a thermogravimetric analyzer (TGA) under a nitrogen flow at 50 °C for 40 min, and the water absorption rate is calculated by dividing the weight loss by the initial weight. If the water absorption rate is lower than 0.5%, it is judged as excellent; between 0.5% and 1%, it is judged as good; between 1% and 2%, it is judged as qualified.

[0238] (2) Chemical resistance test

[0239] The photosensitive resin composition to be tested was coated on a 4-inch square glass substrate by spin coating (250 rpm), pre-baked at 120 °C for 180 s to remove most of the solvent, and the film thickness t was measured. Then, the coated glass substrate was placed in a clean oven at 250 °C and cured for 60 min under nitrogen protection (oxygen concentration < 20 ppm), and the film thickness (t1) was measured using an ellipsometer. The coated glass substrate was immersed in a stripping solution (GES-T01, Glinda Electronic Materials) at 40 °C for 130 s, or immersed in NMP at room temperature for 15 min, taken out and quickly rinsed with deionized water, and then dried in a clean oven at 100 °C under nitrogen protection (oxygen concentration < 20 ppm) for 20 min. The film thickness t2 was measured using an ellipsometer, and the change in film thickness before and after etching was calculated as Δt = ∣(t2 - t1) / t1∣ × 100%. If Δt is less than 1%, it is judged as excellent; between 1% and 2%, it is judged as good; between 2% and 5%, it is judged as qualified.

[0240] The test results are shown in Table 2:

[0241] Table 2

[0242]

[0243]

[0244] According to the performance test results in Table 2, in the photosensitive resin composition provided by the present invention, through the design of the first crosslinking agent and its mutual compounding with components such as the second crosslinking agent and the alkali-soluble resin, the photoresist cured film obtained by high-temperature curing has a low water absorption rate and high chemical corrosion resistance. The water absorption rate < 1%, especially it can be < 0.5%, and it has excellent stability in the stripping solution and NMP. The Δt after etching for 130 s in the stripping solution is < 2%, even < 1%, and the Δt after soaking in NMP for 15 min is < 1%. It can improve the reliability of the device and form an obvious technical advantage. In Comparative Examples 1-8, there is only crosslinking agent B, resulting in an increase in water absorption rate and insufficient chemical resistance; even if the amount of crosslinking agent B is increased (such as in Comparative Examples 7-8), its water absorption rate and chemical resistance cannot be improved.

[0245] The applicant declares that the present invention uses the above embodiments to illustrate the photosensitive resin composition and its application of the present invention, but the present invention is not limited to the above embodiments, that is, 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 improvement of the present invention, the equivalent replacement of each raw material of the product of the present invention, the addition of auxiliary components, and the selection of specific methods, etc., all fall within the protection scope and public scope of the present invention.

Claims

1. A photosensitive resin composition, characterized in that, The photosensitive resin composition comprises an alkali-soluble resin, a photosensitive compound, a combination of a first crosslinking agent and a second crosslinking agent; The first crosslinking agent has a structure shown in Formula I, and the second crosslinking agent has a structure shown in Formula II; Wherein, X and Y each independently represent a C6-C60 aromatic group; R1 is selected from any one of C1-C20 linear or branched alkyl groups and C6-C20 aryl groups; R2 is selected from any one of H and C1-C8 linear or branched alkyl groups; m, p, and q are each independently integers ≥ 1, and n and k are each independently integers ≥ 0; -COOR1 and optionally -COOH are both directly connected to the aromatic ring by a single bond.

2. The photosensitive resin composition according to claim 1, characterized in that, The m is an integer ≥ 2, preferably an integer ≥ 4; Preferably, n + k ≥ 1; Preferably, n and k are each independently integers from 0 to 4, and n + k ≥ 1; Preferably, n is an integer from 1 to 4, and / or k is an integer from 0 to 4; Preferably, 0 < m / (n + m) ≤ 1, more preferably 0.5 < m / (n + m) ≤ 0.

95.

3. The photosensitive resin composition according to claim 1, wherein The first crosslinking agent has a structure shown in Formula IA: Wherein, R1 is each independently selected from any one of C1-C20 linear or branched alkyl groups and C6-C20 aryl groups, preferably any one of C1-C10 linear or branched alkyl groups, more preferably any one of C1-C6 linear or branched alkyl groups; X1 and X2 are each independently selected from a single bond, -O-, -S-, a substituted or unsubstituted C1-C10 linear or branched alkylene group, a substituted or unsubstituted silylene group, or a group in which one or at least two non-connected -CH2- in the C1-C10 linear or branched alkylene group are replaced by -O-, -S-, or a C6-C20 arylene group; The substituents in X1 and X2, R X1 each independently selected from hydroxy, carboxyl, -COOR A1 , unsubstituted or R'-substituted C6-C20 aryl, unsubstituted or R'-substituted C6-C20 aryloxy, or any combination of at least two of them; Each R' is independently selected from a hydroxyl group, a carboxyl group, or -COOR A2 or a combination of any one or at least two of them; R A1 、R A2 Each independently selected from C1-C10 straight-chain or branched-chain alkyl groups; m1, m2, n1, n2, k1, and k2 are each independently selected from integers from 0 to 5, and m1 + m2 ≥ 1, n1 + n2 + k1 + k2 + ≥ 1; s1 and s2 are each independently integers from 0 to 4.

4. The photosensitive resin composition according to claim 3, wherein X1 and X2 are each independently selected from a single bond, a substituted or unsubstituted C1-C10 linear or branched alkylene group, a substituted or unsubstituted silylene group, or a group in which one or at least two non-connected -CH2- in the C1-C10 linear or branched alkylene group are replaced by -O-; Preferably, the substituents of X1 and X2 are each independently selected from any one or a combination of at least two of hydroxyl, carboxyl, -COOR A1 , phenyl which is unsubstituted or substituted with R', and phenoxy which is unsubstituted or substituted with R'. Preferably, each of X1 and X2 is independently selected from a single bond, - *Represents the attachment site of the group; Preferably, the R X1 are each independently selected from any one or a combination of at least two of a hydroxyl group, a carboxyl group, -COOR A1 , an unsubstituted or R'-substituted phenyl group, and an unsubstituted or R'-substituted phenoxy group, more preferably a hydroxyl group, a carboxyl group, -COOR A1 , ; -* represents the connection site of the group.

5. The photosensitive resin composition according to claim 1, wherein The first crosslinking agent is selected from any one or a combination of at least two of the following compounds: wherein R B is independently selected from hydrogen or methyl, and at least one R in a compound B is methyl.

6. The photosensitive resin composition according to claim 1, characterized in that, The molecular weight of the first crosslinking agent is 200-2000, preferably 300-1000; Preferably, based on 100 parts by mass of the alkali-soluble resin, the mass of the first crosslinking agent is 0.1-40 parts, more preferably 0.5-30 parts.

7. The photosensitive resin composition according to claim 1, wherein The second crosslinking agent has a structure shown in any one of Formula IIA, Formula IIB, and Formula IIC: Wherein, R2 is selected from any one of H and C1-C8 linear or branched alkyl groups, more preferably any one of H and C1-C4 linear or branched alkyl groups; Y1 and Y3 are each independently selected from any one of a single bond, -O-, -S-, -CO-, and an unsubstituted or halogen-substituted C1-C10 straight-chain or branched alkylene; Y2 is selected from any one of an unsubstituted or halogen-substituted C1-C10 straight-chain or branched sub-alkylene; p1, p2, p3, q1, q2, q3 are each independently selected from integers from 0 to 5; p4 and q4 are each independently selected from integers from 0 to 4; In formula IIA, p1 + p2 ≥ 1 and q1 + q2 ≥ 1; In formula IIB, p1 + p2 + p3 ≥ 1 and q1 + q2 + q3 ≥ 1; In formula IIC, p1 + p2 + p3 + p4 ≥ 1 and q1 + q2 + q3 + q4 ≥ 1.

8. The photosensitive resin composition according to claim 7, wherein Y1 and Y3 are each independently selected from any one of a single bond, an unsubstituted or halogen-substituted C1-C6 straight or branched alkylene group, preferably a single bond. -* represents the attachment site of the group. Preferably, Y2 is selected from any one of unsubstituted or halogen-substituted C1-C6 straight-chain or branched alkylenes, more preferably 9. The photosensitive resin composition according to claim 1, wherein The second cross-linking agent is selected from any one or a combination of at least two of the following compounds:

10. The photosensitive resin composition according to claim 1, wherein The alkali-soluble resin includes any one or a combination of at least two of polyimide, polyimide precursor resin, polyamic acid-polyimide copolymer, polyamic acid ester-polyimide copolymer, polyisoimide-polyamic acid copolymer, and polyisoimide; Preferably, the alkali-soluble resin contains at least one of the structural units represented by formula III, formula IV, or formula V: Among them, R3, R6, R8, R 11 each independently represents a tetravalent organic group having 4 to 60 carbon atoms; R4, R7, R9, R 12 each independently represents a divalent organic group having 3 to 60 carbon atoms; R5, R 10 Each independently selected from any one of C1-C10 linear or branched alkyl groups.

11. The photosensitive resin composition according to claim 10, wherein The R3, R6, R8, R 11 are each independently selected from any one of a substituted or unsubstituted C6-C30 tetravalent aromatic group and a substituted or unsubstituted C4-C20 tetravalent alicyclic group; R3, R6, R8, R 11 each of the substituents described in 11 is independently selected from at least one of halogen, hydroxyl, unsubstituted or halogen-substituted C1-C20 linear or branched alkyl, and unsubstituted or halogen-substituted C1-C20 alkoxy; Preferably, the R3, R6, R8, R 11 are each independently selected from any one of the following groups: -* represents the attachment site of the group; R 21 、R 22 、R 23 、R 24 、R 25 、R 26 each independently selected from any one of hydrogen, halogen, hydroxy, unsubstituted or halogen-substituted C1-C20 straight-chain or branched-chain alkyl, and unsubstituted or halogen-substituted C1-C20 alkoxy; L 21 Selected from a single bond, -O-, -S-, a carbonyl group, a sulfone group, a sulfoxide group, an unsubstituted or R''-substituted C1-C10 straight-chain or branched alkylene group, an unsubstituted or R''-substituted C6-C20 arylene group, *-L 22 -Ar 21 -L 23 -*; any one of them L 22 and L 23 each independently selected from any one of a single bond, -O-, -S-, a carbonyl group, a sulfone group, a sulfoxide group, an unsubstituted or R''-substituted C1-C10 straight-chain or branched-chain alkylene group; Ar 21 Any one selected from unsubstituted or R”-substituted C6-C20 arylene groups; R” is selected from at least one of halogen, hydroxyl, unsubstituted or halogen-substituted C1-C20 straight-chain or branched alkyl, and unsubstituted or halogen-substituted C1-C20 alkoxy; Preferably, the R3, R6, R8, R 11 are each independently selected from any one of the following groups: Wherein, -* represents the connection site of the group.

12. The photosensitive resin composition according to claim 10, wherein The R4, R7, R9, R 12 are each independently selected from any one of the groups represented by Formula VI, a substituted or unsubstituted C6-C30 divalent aromatic group, and a substituted or unsubstituted C4-C20 divalent alicyclic group; R4, R7, R9, R 12 each of the substituents described in 12 is independently selected from at least one of halogen, hydroxy, unsubstituted or halogen-substituted C1-C20 linear or branched alkyl, and unsubstituted or halogen-substituted C1-C20 alkoxy; -* represents the connection site of the group; A is selected from any one of a single bond, -O-, -S-, carbonyl, 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 in A are each independently selected from at least one of halogen, unsubstituted or halogen-substituted C1-C10 straight-chain or branched alkyl, unsubstituted or halogen-substituted C6-C30 aryl, and unsubstituted or halogen-substituted C6-C30 phenol group; R 31 、R 32 each independently selected from any one of halogen, nitro, cyano, carboxyl, unsubstituted or halogen-substituted C1-C10 straight-chain or branched alkyl, unsubstituted or halogen-substituted C1-C10 alkoxy, unsubstituted or halogen-substituted C6-C30 aryl, amido, benzyloxy or benzyl alcohol group; R 33 and R 34 each independently selected from any one of C1-C10 straight-chain or branched alkylene groups, C1-C10 alkyleneoxy groups, and C1-C10 divalent Si-containing groups; R 35 、R 36 are each independently selected from *-CH2-OR 51 ,wherein R 51 is selected from any one of H, C1-C8 linear or branched alkyl; R 37 、R 38 Each independently selected from any one of halogen, hydroxyl, nitro, cyano, carboxyl, unsubstituted or halogen-substituted C1-C10 straight-chain or branched-chain alkyl, unsubstituted or halogen-substituted C1-C10 alkoxy, unsubstituted or halogen-substituted C6-C30 aryl, C1-C10 ester group or amide group; a1, a2, b1, b2, c1, c2, d1, d2 are each independently selected from integers from 0 to 4; t1 and t2 are each independently 0 or 1; Preferably, the group represented by formula VI has any one of the following structures: Wherein, -* represents the connection site of the group.

13. The photosensitive resin composition according to claim 10, wherein The R4, R7, R9, R 12 are each independently selected from the groups represented by Formula VI, any one of; -* represents the connection site of the group; R 41 、R 42 each independently selected from any one of halogen, hydroxyl, unsubstituted or halogen-substituted C1-C20 straight-chain or branched-chain alkyl, and unsubstituted or halogen-substituted C1-C20 alkoxy; L 41 Selected from a single bond, -O-, -S-, a carbonyl group, a sulfone group, a sulfoxide group, an unsubstituted or halogen-substituted C1-C10 straight-chain or branched alkylene group, an unsubstituted or halogen-substituted C6-C20 arylene group, *-L 42 -Ar 41 -L 43 -*, any one of them; L 42 and L 43 each independently selected from any one of a single bond, -O-, -S-, a carbonyl group, a sulfone group, a sulfoxide group, an unsubstituted or halogen-substituted C1-C10 straight-chain or branched-chain alkylene group; Ar 41 Any one selected from 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 from 0 to 4; Preferably, the R4, R7, R9, R 12 are each independently selected from the groups represented by Formula VI, and any one of them.

14. The photosensitive resin composition according to claim 1, wherein The weight-average molecular weight of the alkali-soluble resin is 2000-100000, preferably 5000-50000; Preferably, the photosensitive compound is a compound containing a diazonaphthoquinone group; Preferably, the photosensitive resin composition further includes an additive; Preferably, the additive includes any one or a combination of at least two of a silane coupling agent, a surfactant, and a curing accelerator.

15. The photosensitive resin composition according to any one of claims 1 to 14, characterized in that The photosensitive resin composition includes the following components by mass parts:

16. The photosensitive resin composition according to claim 1, wherein The photosensitive resin composition further includes a solvent; Preferably, the amount of the solvent is such that the solid content of the photosensitive resin composition is 5-45 wt%.

17. A photoresist cured film, characterized in that, The photoresist cured film is prepared from the photosensitive resin composition according to any one of claims 1-16.

18. Use of the photosensitive resin composition according to any one of claims 1-16 and the photoresist cured film according to claim 17 in semiconductor devices or flat panel display devices.

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