Tetrazolyl silane coupling agent and preparation method therefor, photosensitive resin composition and preparation method therefor and use thereof

Abstract

The present invention relates to the technical field of photosensitive resins. The present invention provides a tetrazolyl silane coupling agent and a preparation method therefor, a photosensitive resin composition and a preparation method therefor and a use thereof. According to the tetrazolyl silane coupling agent of the present invention, a tetrazolyl compound containing more active N atoms is bonded to silane having excellent thermodynamic stability and interface bonding performance, and the tetrazolyl silane coupling agent is added to a photosensitive resin composition, so that the use amount of an additive can be reduced, the bonding force of PSPI and a copper surface is improved, the formation of pores and oxide layer particles at the joint of the PSPI and the copper surface is inhibited, and the bottle opening stability for optimizing the bonding force of the copper surface is improved.

Description

A tetrazolylsilane coupling agent and its preparation method, a photosensitive resin composition and its preparation method and application Technical Field

[0001] The present invention relates to the technical field of photosensitive resins, and in particular to a tetrazolyl silane coupling agent and a preparation method thereof, a photosensitive resin composition and a preparation method and application thereof. Background Art

[0002] Photosensitive polyimide (PSPI) material is widely used for surface passivation of integrated circuit chips and in surface redistribution layout (RDL) processes for wafer-level and panel-level packaging. It is an essential key material in wafer-level advanced packaging processes. In RDL processes, the interface between PSPI material and copper traces and pillars plays a critical role in the reliability of the package structure. During high-temperature and high-humidity aging tests of package structures, the following issues are commonly observed: 1. Delamination of the PSPI-copper interface; 2. Formation of voids at the PSPI-copper interface; 3. Formation of a thick oxide layer or oxide particles at the PSPI-copper interface; 4. Impact of bottle opening stability on the copper surface bond, thus affecting the reliability and stability of the package structure.

[0003] Prior art techniques enhance the adhesion of PSPI to the copper interface and protect the copper surface by adding purine and imidazole compounds to resin compositions. However, purine compounds have high molecular acidity, weak electron-donating ability, low boiling points, and poor thermal and chemical stability. Therefore, they are ineffective in inhibiting the formation of oxide layers or oxidized particles on the copper surface and improving the stability of the opening. Imidazole compounds, due to the low number of active nitrogen atoms per molecule, have a poor effect on improving the adhesion to the copper surface. Therefore, increasing the additive dosage can negatively impact the resolution of the photolithographic pattern and the stability of the opening.

[0004] Based on the existing defects of adding purine compounds and imidazole compounds to the resin composition to improve the bonding strength between PSPI and copper interface and protect the copper surface, it is necessary to improve this.

[0005] Summary of the Invention

[0006] In view of this, the present invention proposes a tetrazolyl silane coupling agent and a preparation method thereof, a photosensitive resin composition and a preparation method and application thereof, in order to solve the technical problems existing in the prior art.

[0007] In a first aspect, the present invention provides a tetrazolyl silane coupling agent, the structural formula of the tetrazolyl silane coupling agent is shown in the following formula (I) or (II);

[0008] wherein R1, R2, and R3 are each independently selected from any one of a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or an aromatic group;

[0009] R4 is selected from any one of a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, an amino group, an alkyl group having 1 to 10 carbon atoms, or an aromatic group;

[0010] R5 is selected from any one of a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, an amino group, an alkyl group having 1 to 10 carbon atoms, or an aromatic group;

[0011] n is a positive integer between 1 and 20.

[0012] Preferably, the tetrazolyl silane coupling agent has a structural formula including any one of the following formulae:

[0013] In a second aspect, the present invention further provides a method for preparing a tetrazolyl silane coupling agent, comprising the following steps:

[0014] The first compound and the third compound are subjected to an amidation reaction to obtain a tetrazolyl silane coupling agent represented by formula (I);

[0015] The second compound and the third compound are subjected to an imidization reaction to obtain a tetrazolyl silane coupling agent represented by formula (II);

[0016] Wherein, the structural formula of the first compound is:

[0017] The structural formula of the second compound is:

[0018] The structural formula of the third compound is:

[0019] Preferably, the preparation method of the tetrazolyl silane coupling agent comprises adding the first compound or the second compound to a first organic solvent, then adding the third compound, reacting at 45-55° C. for 2-3 hours, cooling to room temperature, adding pyridine, stirring, and then adding acetic anhydride, reacting at room temperature for 18-22 hours, and after completion of the amidation reaction, distilling under reduced pressure to obtain the tetrazolyl silane coupling agent.

[0020] Preferably, in the preparation method of the tetrazolyl silane coupling agent, the first compound is 1-aminotetrazolyl, the second compound is 5-aminotetrazolyl, and the third compound is 3-(triethoxysilyl)propyl succinic anhydride or [3-(trimethoxysilyl)propyl]succinic anhydride;

[0021] The first organic solvent includes one or more of N-methylpyrrolidone, dimethyl sulfoxide, and N,N-dimethylacetamide;

[0022] The molar ratio of the first compound or the second compound, the third compound, pyridine, and acetic anhydride is (0.05-0.15):(0.05-0.15):(0.1-0.3):(0.1-0.3);

[0023] The molar volume ratio of the first compound or the second compound to the first organic solvent is (0.05-0.15) mol: (200-300) mL.

[0024] In a third aspect, the present invention further provides a photosensitive resin composition comprising the tetrazolyl silane coupling agent, a polyimide precursor and a photopolymerization initiator.

[0025] Preferably, in the photosensitive resin composition, the structural formula of the polyimide precursor is:

[0026] wherein R6 is a tetravalent organic group having 6 to 50 carbon atoms;

[0027] R7 is a divalent organic group having 6 to 50 carbon atoms;

[0028] R8 and R9 are each independently selected from a hydrogen atom, an organic group having 2 to 30 carbon atoms and at least one free radical polymerizable unsaturated bond group, and a saturated aliphatic group having 1 to 10 carbon atoms;

[0029] n1 is a positive integer between 1 and 1000;

[0030] and / or, the photopolymerization initiator is an oxime ester photoinitiator;

[0031] And / or, the mass ratio of the polyimide precursor, the tetrazolylsilane coupling agent and the photopolymerization initiator is 100:(0.1-20):(0.5-50).

[0032] And / or, the quadrivalent organic group includes any one of 4,4'-oxydiphthalic anhydride and pyromellitic dianhydride;

[0033] And / or, the divalent organic group includes any one of 4,4'-diaminodiphenyl ether and p-phenylenediamine;

[0034] And / or, the organic group having at least one free radical polymerizable unsaturated bond group includes any one of a hydroxyl group, an acrylic group, and a methacrylic group.

[0035] In a fourth aspect, the present invention further provides a method for preparing the photosensitive resin composition, comprising the following steps:

[0036] A tetrazolylsilane coupling agent, a polyimide precursor and a photopolymerization initiator are added into the second solvent to obtain a photosensitive resin composition.

[0037] Preferably, the method for preparing the photosensitive resin composition comprises adding a tetrazolylsilane coupling agent, a polyimide precursor, a photopolymerization initiator, and a photocrosslinking agent to a second solvent, and adjusting the viscosity of the system to 25 to 35 poises to obtain the photosensitive resin composition;

[0038] The mass ratio of the polyimide precursor, tetrazolylsilane coupling agent, photopolymerization initiator, and photocrosslinking agent is 100:(0.1-20):(0.5-50):(5-15);

[0039] And / or, the preparation method of the polyimide precursor comprises the following steps:

[0040] Adding 4,4'-oxydiphthalic anhydride or pyromellitic dianhydride to a third solvent, and then adding hydroxyethyl methacrylate and pyridine, to obtain a first mixture through reaction;

[0041] adding dicyclohexylcarbodiimide to the first mixture and continuing the reaction to obtain a second mixture;

[0042] Adding 4,4'-diaminodiphenyl ether or p-phenylenediamine to the second mixture to obtain a polyimide precursor through reaction;

[0043] The mass ratio of the 4,4'-oxydiphthalic anhydride or pyromellitic dianhydride, hydroxyethyl methacrylate, pyridine, dicyclohexylcarbodiimide, 4,4'-diaminodiphenyl ether or p-phenylenediamine is (70-120):(70-100):(2-6):(120-150):(30-80).

[0044] In a fifth aspect, the present invention also provides an application of the photosensitive resin composition or the photosensitive resin composition prepared by the preparation method in wafer-level packaging rewiring process, circuit packaging of structural devices, insulation protection of semiconductor components, and insulation buffering of OLED components.

[0045] The tetrazolylsilane coupling agent and its preparation method, the photosensitive resin composition and its preparation method and application of the present invention have the following beneficial effects compared with the prior art:

[0046] The tetrazolylsilane coupling agent of the present invention introduces benzodiimidazole and benzotriazole imidazole compounds with higher thermal and chemical stability and containing more active nitrogen atoms. When added to a photosensitive resin composition, the amount of additives used can be reduced, the bonding strength between PSPI and a copper surface can be improved, the formation of pores and oxide layer particles at the interface between PSPI and copper can be suppressed, and the bottle opening stability can be improved to optimize the bonding strength to the copper surface. DETAILED DESCRIPTION

[0047] The following will be combined with the embodiments of the present invention to clearly and completely describe the technical solutions in the embodiments of the present invention. Obviously, the embodiments described are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without making creative efforts are within the scope of protection of the present invention.

[0048] For a better understanding of the present invention and not to limit the scope of the present invention, all numbers used in this application to express amounts, percentages, and other numerical values ​​should be understood as modified by the word "about" in all cases. Therefore, unless otherwise specified, the numerical parameters listed in the specification and the appended claims are approximate values, which may vary depending on the desired properties to be obtained. Each numerical parameter should at least be regarded as obtained based on the reported significant figures and by conventional rounding methods.

[0049] It should be noted that the order of description of the following embodiments is not intended to limit the preferred order of the embodiments. In addition, in the description of this application, the term "including" means "including but not limited to". Various embodiments of the present invention may be presented in the form of a range; it should be understood that the description in the form of a range is merely for convenience and brevity and should not be understood as a rigid limitation on the scope of the invention; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single numerical values ​​within the range. For example, the range description from 1 to 6 should be considered to have specifically disclosed sub-ranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as single numbers within the range, such as 1, 2, 3, 4, 5 and 6, regardless of the range. In addition, whenever a numerical range is indicated herein, it is meant to include any cited number (fractional or integer) within the indicated range.

[0050] The embodiment of the present invention provides a tetrazolyl silane coupling agent, the structural formula of which is shown in the following formula (I) or (II);

[0051] wherein R1, R2, and R3 are each independently selected from any one of a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or an aromatic group;

[0052] R4 is selected from any one of a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, an amino group, an alkyl group having 1 to 10 carbon atoms, or an aromatic group;

[0053] R5 is selected from any one of a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, an amino group, an alkyl group having 1 to 10 carbon atoms, or an aromatic group;

[0054] n is a positive integer between 1 and 20.

[0055] It should be noted that the tetrazolyl silane coupling agent of the present invention, by introducing benzodiimidazole and benzotriazole imidazole compounds with higher thermal and chemical stability and containing more active nitrogen atoms, can reduce the amount of additives used in the photosensitive resin composition, improve the bonding strength between PSPI and the copper surface, inhibit the formation of pores and oxide layer particles at the interface between PSPI and copper, and improve the opening stability of the bottle, which optimizes the bonding strength to the copper surface.

[0056] Preferably, the structural formula of the tetrazolyl silane coupling agent includes any one of the following formulae:

[0057] Based on the same inventive concept, the present invention also provides a method for preparing a tetrazolyl silane coupling agent, comprising the following steps:

[0058] S1, subjecting the first compound to an amidation reaction with the third compound to obtain a tetrazolyl silane coupling agent represented by formula (I);

[0059] S2, performing an imidization reaction on the second compound and the third compound to obtain a tetrazolyl silane coupling agent represented by formula (II);

[0060] Wherein, the structural formula of the first compound is:

[0061] The structural formula of the second compound is:

[0062] The structural formula of the third compound is:

[0063] In some embodiments, the first compound or the second compound is added to a first organic solvent, and then the third compound is added, and the mixture is reacted at 45-55° C. to obtain a tetrazolyl silane coupling agent.

[0064] In some embodiments, the first compound or the second compound is added to a first organic solvent, and then the third compound is added. The mixture is reacted at 45-55°C for 2-3 hours and then cooled to room temperature (25°C). Pyridine is then added, and acetic anhydride is added after stirring. The mixture is reacted at room temperature for 18-22 hours. After the amidation reaction is completed, the mixture is distilled under reduced pressure to obtain a tetrazolyl silane coupling agent.

[0065] In some embodiments, the molar ratio of the first compound or the second compound, the third compound, pyridine, and acetic anhydride is (0.05-0.15):(0.05-0.15):(0.1-0.3):(0.1-0.3).

[0066] In some embodiments, the molar volume ratio of the first compound or the second compound to the first organic solvent is (0.05-0.15) mol: (200-300) mL.

[0067] In some embodiments, the first compound is 1-aminotetrazolyl, the second compound is 5-aminotetrazolyl, and the third compound is 3-(triethoxysilyl)propyl succinic anhydride or [3-(trimethoxysilyl)propyl]succinic anhydride.

[0068] In some embodiments, the first organic solvent includes one or more of N-methylpyrrolidone, dimethyl sulfoxide, and N,N-dimethylacetamide.

[0069] In some embodiments, the preparation method of the tetrazolyl silane coupling agent comprises the following steps:

[0070] 1-aminotetrazole or 5-aminotetrazole is added to a first organic solvent, nitrogen is introduced at 45-55° C. and stirred to dissolve the 1-aminotetrazole or 5-aminotetrazole, and then 3-(triethoxysilyl)propyl succinic anhydride or [3-(trimethoxysilyl)propyl] succinic anhydride is added. After the addition is completed, the reaction is continued at 45-55° C. for 2-3 hours and then cooled to room temperature. Pyridine (as a chemical imidization catalyst) is added, and after stirring, acetic anhydride (as a dehydrating agent) is added. The reaction is carried out at room temperature for 18-22 hours. After the amidation reaction is completed, the solvent, acetic anhydride, and generated acetic acid and pyridine in the system are removed by reduced pressure distillation to obtain a purified tetrazolyl silane coupling agent.

[0071] Specifically, in the above embodiment, the molar ratio of 1-aminotetrazole or 5-aminotetrazole, 3-(triethoxysilyl)propyl succinic anhydride (or [3-(trimethoxysilyl)propyl] succinic anhydride), pyridine, and acetic anhydride is (0.05-0.15):(0.05-0.15):(0.1-0.3):(0.1-0.3); the molar volume ratio of 1-aminotetrazole to the first organic solvent is (0.05-0.15) mol:(200-300) mL.

[0072] Based on the same inventive concept, the present invention further provides a photosensitive resin composition comprising the above-mentioned tetrazolyl silane coupling agent, a polyimide precursor and a photopolymerization initiator.

[0073] The photosensitive resin composition of the present invention contains a tetrazolylsilane coupling agent, which can improve the bonding strength between PSPI and the copper surface, inhibit the formation of pores and oxide layer particles at the interface between PSPI and copper, and improve the bottle opening stability for optimizing the bonding strength to the copper surface.

[0074] In some embodiments, the polyimide precursor has the structural formula:

[0075] wherein R6 is a tetravalent organic group having 6 to 50 carbon atoms;

[0076] R7 is a divalent organic group having 6 to 50 carbon atoms;

[0077] R8 and R9 are each independently selected from a hydrogen atom, an organic group having 2 to 30 carbon atoms and at least one free radical polymerizable unsaturated bond group, and a saturated aliphatic group having 1 to 10 carbon atoms;

[0078] n1 is a positive integer between 1 and 1000.

[0079] In some embodiments, the photopolymerization initiator is an oxime ester photoinitiator, for example, BASF Irgacure OXE 01.

[0080] In some embodiments, the mass ratio of the polyimide precursor, the tetrazolyl silane coupling agent, and the photopolymerization initiator is 100:(0.1-20):(0.5-50).

[0081] In some embodiments, the photosensitive resin composition includes a tetrazolyl silane coupling agent, a polyimide precursor, a photopolymerization initiator and a photocrosslinker, and the mass ratio of the polyimide precursor, the tetrazolyl silane coupling agent, the photopolymerization initiator and the photocrosslinker is 100:(0.1~20):(0.5~50):(5~15).

[0082] In some embodiments, the tetravalent organic group includes, but is not limited to, any one or a combination of two or more of the following structures:

[0083] In some embodiments, the divalent organic group includes but is not limited to any one or a combination of two or more of the following structures:

[0084] In some embodiments, the organic group having at least one free-radically polymerizable unsaturated bond group includes any one of a hydroxyl group, an acrylic group, and a methacrylic group.

[0085] Based on the same inventive concept, the present invention also provides a method for preparing the above-mentioned photosensitive resin composition, comprising the following steps:

[0086] A tetrazolylsilane coupling agent, a polyimide precursor and a photopolymerization initiator are added into the second solvent to obtain a photosensitive resin composition.

[0087] In some embodiments, a tetrazolyl silane coupling agent, a polyimide precursor, a photopolymerization initiator, and a photocrosslinking agent are added to the second solvent, and the viscosity of the system is adjusted to 25-35 poise to obtain a photosensitive resin composition.

[0088] In the above embodiments, a photocrosslinking agent is used to promote the photopolymerization reaction, and the photocrosslinking agent used includes but is not limited to tetraethylene glycol dimethacrylate.

[0089] In some embodiments, the second solvent includes one or more of N-methylpyrrolidone, dimethyl sulfoxide, N,N-dimethylacetamide, and γ-butyrolactone.

[0090] Specifically, in the above embodiment, a negative photosensitive resin composition is obtained by adding a tetrazolylsilane coupling agent, a polyimide precursor, a photopolymerization initiator, and a photocrosslinker to a second solvent, and adjusting the amount of the second solvent to adjust the viscosity of the system to 25 to 35 poises.

[0091] In some embodiments, the method for preparing a polyimide precursor comprises the following steps:

[0092] S1. Adding 4,4'-oxydiphthalic anhydride or pyromellitic dianhydride to a third solvent, and then adding hydroxyethyl methacrylate and pyridine to obtain a first mixture through reaction;

[0093] S2, adding dicyclohexylcarbodiimide to the first mixture, and continuing the reaction to obtain a second mixture;

[0094] S3. Adding 4,4'-diaminodiphenyl ether or p-phenylenediamine to the second mixture to obtain a polyimide precursor through reaction.

[0095] Specifically, in step S2 of the above embodiment, adding dicyclohexylcarbodiimide to the first mixture is specifically as follows: first adding dicyclohexylcarbodiimide to the third solvent, and then adding the third solvent containing dicyclohexylcarbodiimide to the first mixture; in step S3, adding 4,4'-diaminodiphenyl ether or p-phenylenediamine to the second mixture is specifically as follows: first adding 4,4'-diaminodiphenyl ether or p-phenylenediamine to the third solvent, and then adding the third solvent containing 4,4'-diaminodiphenyl ether or p-phenylenediamine to the second mixture.

[0096] In some embodiments, the method for preparing a polyimide precursor comprises the following steps:

[0097] S1, adding 4,4'-oxydiphthalic anhydride or pyromellitic dianhydride to a third solvent, and then adding hydroxyethyl methacrylate and pyridine, and reacting at room temperature for 15 to 20 hours to obtain a first mixture;

[0098] S2, adding dicyclohexylcarbodiimide to the third solvent, mixing, and then adding dropwise to the first mixture, and continuing the reaction for 1 to 3 hours to obtain a second mixture;

[0099] S3, adding 4,4'-diaminodiphenyl ether or p-phenylenediamine to the third solvent under a nitrogen atmosphere, mixing, and then adding dropwise to the second mixture for 4 to 8 hours. After the reaction is completed, adding an alcohol or an amine (such as ethanol or ethylamine) as a quencher and reacting for 2 to 3 hours;

[0100] S4. Filter the quenched reaction liquid, and immediately add the filtrate into methanol to precipitate a blocky solid. Refrigerate for 12 hours, then dissolve it and dropwise add it into water. Filter and dry to obtain the corresponding polyimide precursor.

[0101] In some embodiments, the mass ratio of 4,4'-oxydiphthalic anhydride or pyromellitic dianhydride, hydroxyethyl methacrylate, pyridine, dicyclohexylcarbodiimide, 4,4'-diaminodiphenyl ether or p-phenylenediamine is (70-120):(70-100):(2-6):(120-150):(30-80).

[0102] In some embodiments, in the step of adding 4,4'-oxydiphthalic anhydride or pyromellitic dianhydride to the third solvent in S1, the mass volume ratio of 4,4'-oxydiphthalic anhydride or pyromellitic dianhydride to the third solvent is (70-120) g:(120-160) mL; in the step of adding dicyclohexylcarbodiimide to the third solvent in S2, the mass volume ratio of dicyclohexylcarbodiimide to the third solvent is (120-150) g:(140-180) mL; in the step of adding 4,4'-diaminodiphenyl ether or p-phenylenediamine to the third solvent under a nitrogen atmosphere in S3, the mass volume ratio of 4,4'-diaminodiphenyl ether or p-phenylenediamine to the third solvent is (30-80) g:(80-100) mL.

[0103] Based on the same inventive concept, the present invention also provides an application of the above-mentioned photosensitive resin composition or the photosensitive resin composition prepared by the above-mentioned preparation method in circuit packaging; specifically, the application of the above-mentioned photosensitive resin composition in the surface passivation of integrated circuit chips, wafer-level packaging rewiring (RDL) process, circuit packaging of structural devices, insulation protection of semiconductor components, insulation buffering of OLED components, etc.

[0104] The following further illustrates the tetrazolylsilane coupling agent and its preparation method, the photosensitive resin composition and its preparation method and application of the present application with specific examples. This section further illustrates the present invention with reference to specific examples, but should not be construed as limiting the present invention. Unless otherwise specified, the technical means used in the examples are conventional means well known to those skilled in the art. Unless otherwise specified, the reagents, methods, and equipment used in the present invention are conventional reagents, methods, and equipment in the art.

[0105] Example 1

[0106] This embodiment provides a tetrazolyl silane coupling agent, the structural formula of which is:

[0107] The preparation method of the tetrazolyl silane coupling agent comprises the following steps:

[0108] 0.1 mol of 1-aminotetrazole was added to 250 mL of N-methylpyrrolidone solvent, and nitrogen was introduced at 50°C with stirring to dissolve the 1-aminotetrazole. Then, 0.1 mol of [3-(trimethoxysilyl)propyl]succinic anhydride was added. After the addition was completed, the reaction was continued at 50°C for 2 hours, and then cooled to room temperature. 0.2 mol of pyridine was added, and after stirring, 0.2 mol of acetic anhydride was added. The reaction was continued at room temperature for 20 hours. After the reaction was completed, the solvent, acetic anhydride, and generated acetic acid and pyridine in the system were removed by distillation under reduced pressure to obtain purified tetrazolyl silane coupling agent C1.

[0109] Example 2

[0110] This embodiment provides a tetrazolyl silane coupling agent, the structural formula of which is:

[0111] The preparation method of the tetrazolyl silane coupling agent comprises the following steps:

[0112] 0.1 mol of 5-aminotetrazole was added to 250 mL of N-methylpyrrolidone solvent, and nitrogen was introduced at 50° C. with stirring to dissolve the 5-aminotetrazole. Then, 0.1 mol of 3-(triethoxysilyl)propyl succinic anhydride (Silane GF20, WACKER CHEMIE AG, Munich) was added. After the addition was completed, the reaction was continued at 50° C. for 2 h, and then cooled to room temperature. 0.2 mol of pyridine was added, and after stirring evenly, 0.2 mol of acetic anhydride was added. The reaction was continued at room temperature for 20 h. After the reaction was completed, the solvent, acetic anhydride, and generated acetic acid and pyridine in the system were removed by distillation under reduced pressure to obtain purified tetrazolyl silane coupling agent C2.

[0113] Example 3

[0114] The present invention provides a method for preparing a polyimide precursor, comprising the following steps:

[0115] S1. Add 103 g of 4,4'-oxydiphthalic anhydride (ODPA) to 200 mL of γ-butyrolactone (GBL), then add 87 g of hydroxyethyl methacrylate (HEMA), and then dropwise add 3 g of pyridine, and react at room temperature for 16 h to obtain a first mixture;

[0116] S2. Add 137 g of dicyclohexylcarbodiimide (DCC) to 100 mL of γ-butyrolactone (GBL) to obtain a first mixture, and then add the first mixture to the first mixture and stir for 2 h to obtain a second mixture;

[0117] S3. Add 67 g of 4,4'-diaminodiphenyl ether (ODA) to 300 mL of γ-butyrolactone (GBL) under a nitrogen atmosphere to obtain a second mixture, and then add the second mixture to the second mixture and react for 6 h. After the reaction is completed, add 20 mL of ethanol as a quencher and react for 2 h.

[0118] S4. Filter the quenched reaction liquid in S3, collect the filtrate, add methanol to the filtrate to precipitate block solids, collect the block solids and refrigerate for 12 hours, then add 800 mL of GBL and stir, after it is completely dissolved, add dropwise into water to precipitate white flocculent material, filter and dry to obtain the corresponding polyimide precursor A1.

[0119] Example 4

[0120] This embodiment of the present application provides a method for preparing a polyimide precursor, which is the same as that of Example 3, except that 72.7 g of pyromellitic dianhydride (PMDA) is used in step S1 instead of 103 g of 4,4'-oxydiphthalic anhydride (ODPA) in Example 3. The remaining process steps are the same as those of Example 3, and a polyimide precursor A2 is finally prepared.

[0121] Example 5

[0122] This embodiment of the present application provides a method for preparing a polyimide precursor, which is the same as that of Example 3, except that 36 g of p-phenylenediamine (PPDA) is used in step S3 instead of 67 g of 4,4'-diaminodiphenyl ether (ODA) in Example 3. The remaining process steps are the same as those of Example 3, and a polyimide precursor A3 is finally prepared.

[0123] Example 6

[0124] The embodiment of the present application provides a photosensitive resin composition, including: 20g of polyimide precursor A1, 0.8g of photopolymerization initiator BASF Irgacure OXE 01 (No. B1), 0.02g of tetrazolyl silane coupling agent C1, and 2.0g of tetraethylene glycol dimethacrylate.

[0125] The preparation method of the photosensitive resin composition comprises the following steps:

[0126] Under a constant temperature and humidity environment (24°C, 50% RH), 20 g of polyimide precursor resin A1, 35 g of N-methylpyrrolidone (NMP) solvent, 0.8 g of photopolymerization initiator BASF Irgacure OXE 01 (No. B1), 0.02 g of tetrazolyl silane coupling agent C1, and 2.0 g of tetraethylene glycol dimethacrylate were added to a 100 mL brown plastic bottle in sequence. After shaking on a shaker for 24 hours, 2 g of N-methylpyrrolidone (NMP) solvent was added to adjust the viscosity of the resulting solution to approximately 30 poise to prepare a negative photosensitive resin composition.

[0127] Example 7

[0128] The photosensitive resin composition provided in the embodiment of the present application is the same as that in Example 6, except that 0.02 g of tetrazolyl silane coupling agent C1 in Example 6 is replaced by 0.02 g of tetrazolyl silane coupling agent C2.

[0129] The preparation method of the photosensitive resin composition is the same as that of Example 6, except that 0.02 g of tetrazolyl silane coupling agent C1 in Example 6 is replaced by 0.02 g of tetrazolyl silane coupling agent C2.

[0130] Example 8

[0131] The photosensitive resin composition provided in the embodiment of the present application is the same as that in Example 6, except that 0.02 g of tetrazolyl silane coupling agent C1 in Example 6 is replaced with 0.01 g of tetrazolyl silane coupling agent C1.

[0132] The preparation method of the above-mentioned photosensitive resin composition is the same as that of Example 6, except that 0.02 g of tetrazolyl silane coupling agent C1 in Example 6 is replaced by 0.01 g of tetrazolyl silane coupling agent C1.

[0133] Example 9

[0134] The photosensitive resin composition provided in the embodiment of the present application is the same as that in Example 6, except that 0.02 g of tetrazolyl silane coupling agent C1 in Example 6 is replaced by 0.01 g of tetrazolyl silane coupling agent C2.

[0135] The preparation method of the photosensitive resin composition is the same as that of Example 6, except that 0.02 g of tetrazolyl silane coupling agent C1 in Example 6 is replaced by 0.01 g of tetrazolyl silane coupling agent C2.

[0136] Example 10

[0137] The photosensitive resin composition provided in the embodiment of the present application is the same as that in Example 6, except that 20 g of the polyimide precursor A1 in Example 6 is replaced by 20 g of the polyimide precursor resin A2.

[0138] The preparation method of the above-mentioned photosensitive resin composition is the same as that of Example 6, except that 20 g of the polyimide precursor A1 in Example 6 is replaced by 20 g of the polyimide precursor resin A2.

[0139] Example 11

[0140] The photosensitive resin composition provided in the embodiment of the present application is the same as that in Example 6, except that 20 g of polyimide precursor A1 in Example 6 is replaced by 20 g of polyimide precursor resin A2, and 0.02 g of tetrazolyl silane coupling agent C1 is replaced by 0.02 g of tetrazolyl silane coupling agent C2.

[0141] The preparation method of the above-mentioned photosensitive resin composition is the same as that of Example 6, except that 20g of polyimide precursor A1 in Example 6 is replaced by 20g of polyimide precursor resin A2, and 0.02g of tetrazolyl silane coupling agent C1 is replaced by 0.02g of tetrazolyl silane coupling agent C2.

[0142] Example 12

[0143] The photosensitive resin composition provided in the embodiment of the present application is the same as that in Example 6, except that 20 g of the polyimide precursor A1 in Example 6 is replaced by 20 g of the polyimide precursor resin A3.

[0144] The preparation method of the photosensitive resin composition is the same as that of Example 6, except that 20 g of the polyimide precursor A1 in Example 6 is replaced by 20 g of the polyimide precursor resin A3.

[0145] Example 13

[0146] The photosensitive resin composition provided in the embodiment of the present application is the same as that in Example 6, except that 20 g of polyimide precursor A1 in Example 6 is replaced by 20 g of polyimide precursor resin A3, and 0.02 g of tetrazolyl silane coupling agent C1 is replaced by 0.02 g of tetrazolyl silane coupling agent C2.

[0147] The preparation method of the above-mentioned photosensitive resin composition is the same as that of Example 6, except that 20g of polyimide precursor A1 in Example 6 is replaced by 20g of polyimide precursor resin A3, and 0.02g of tetrazolyl silane coupling agent C1 is replaced by 0.02g of tetrazolyl silane coupling agent C2.

[0148] Comparative Example 1

[0149] The photosensitive resin composition provided in this comparative example is the same as that in Example 6, except that it does not contain the tetrazolyl silane coupling agent C1.

[0150] The preparation method of the above-mentioned photosensitive resin composition is the same as that of Example 6, except that the tetrazolylsilane coupling agent C1 is not added during the preparation process.

[0151] Comparative Example 2

[0152] The photosensitive resin composition provided in this comparative example is the same as that in Example 6, except that 0.02 g of the tetrazolylsilane coupling agent C1 in Example 6 is replaced by 0.02 g of adenine.

[0153] The preparation method of the above-mentioned photosensitive resin composition is the same as that of Example 6, except that 0.02 g of tetrazolylsilane coupling agent C1 in Example 6 is replaced by 0.02 g of adenine.

[0154] Comparative Example 3

[0155] The photosensitive resin composition provided in this comparative example is the same as that in Example 6, except that 0.02 g of the tetrazolyl silane coupling agent C1 in Example 6 is replaced by 0.02 g of benzimidazole.

[0156] The preparation method of the above-mentioned photosensitive resin composition is the same as that of Example 6, except that 0.02 g of tetrazolyl silane coupling agent C1 in Example 6 is replaced by 0.02 g of benzimidazole.

[0157] Comparative Example 4

[0158] The photosensitive resin composition provided in this comparative example is the same as that in Example 6, except that 0.02 g of the tetrazolyl silane coupling agent C1 in Example 6 is replaced by 0.02 g of benzotriazole.

[0159] The preparation method of the above-mentioned photosensitive resin composition is the same as that of Example 6, except that 0.02 g of tetrazolyl silane coupling agent C1 in Example 6 is replaced by 0.02 g of benzotriazole.

[0160] Comparative Example 5

[0161] The photosensitive resin composition provided in this comparative example is the same as that in Example 6, except that 0.02 g of the tetrazolyl silane coupling agent C1 in Example 6 is replaced by 0.1 g of benzotriazole.

[0162] The preparation method of the above-mentioned photosensitive resin composition is the same as that of Example 6, except that 0.02 g of tetrazolyl silane coupling agent C1 in Example 6 is replaced by 0.1 g of benzotriazole.

[0163] Performance Testing

[0164] 1. Polyimide precursor weight average molecular weight test:

[0165] The weight-average molecular weights of the polyimide precursors involved in the present invention were all obtained by testing using an ultra-high performance polymer chromatography analyzer (ACQUITY APC). The relevant testing conditions were as follows: the chromatographic column model was ACQUITY APC XT200 2.5 μm, the column oven and detector temperatures were both 40° C., the mobile phase was THF, and the flow rate was 0.5 mL / min.

[0166] 2. Preparation and evaluation methods of photolithographic patterns:

[0167] The photosensitive resin compositions prepared in the above examples were spin-coated on an 8-inch silicon wafer using a spin coater (WS-650Mz-8NPPB, MYCRO) and pre-baked on a hot plate at 100°C for 240 seconds to form a coating film about 15 μm thick. The coating film was then irradiated with a GHI-Line stepper (Shanghai Microelectronics) using a mask with a test pattern at 400 mJ / cm 2energy. Next, the coating film was spray-developed using cyclopentanone as a developer using a developer (MST-EF1-DV, Shenzhen Kaierdi) and rinsed with propylene glycol methyl ether acetate to obtain a photoresist pattern. A temperature-programmed curing oven (HCM-500D, Shanghai Siwang Electronics) was used to heat treat the film at 350°C for 2 hours under a nitrogen atmosphere to obtain a cured photoresist pattern approximately 10 μm thick formed of resin.

[0168] The cured photoresist pattern obtained above was sliced ​​and analyzed using a focused ion beam electron microscope (FIB, Helios G4, Thermo Fisher) to evaluate its photoresist accuracy and cross-sectional morphology profile, and then the photoresist performance of the negative photosensitive resin composition was evaluated:

[0169] “Optimal”: The photolithography line resolution accuracy is less than 10μm.

[0170] “Excellent”: The photolithography line resolution accuracy is 10μm to 20μm.

[0171] “Excellent”: The photolithography line resolution accuracy is 20μm to 50μm.

[0172] “Poor”: The photolithography line resolution accuracy is above 50μm.

[0173] “Poor”: The photolithography line resolution accuracy is 100μm or none.

[0174] 3. Copper surface adhesion test:

[0175] The photosensitive resin compositions prepared in the above examples were spin-coated onto a copper substrate using a spin coater (WS-650Mz-8NPPB, MYCRO) and pre-baked on a hot plate at 100°C for 240 seconds to form a coating film approximately 15 μm thick. A temperature-programmed curing oven (HCM-500D, Shanghai Siwang Electronics) was used to heat the copper substrate at 350°C for 2 hours under a nitrogen atmosphere to obtain a cured resin film approximately 10 μm thick. The coated copper substrate was placed in a high-temperature, high-humidity accelerated aging test chamber (EHS-222MD, ESPEC) at 130°C and 85% RH for 264 hours. After the accelerated aging test, the adhesion properties of the cured resin film to the copper surface were evaluated using the crosscut method according to JIS K 5600-5-6:

[0176] "Optimal": The grid number is 100, 100% no shedding.

[0177] "Excellent": The number of grids is 90-99, and the grid shedding rate is within 10%.

[0178] “Excellent”: The number of grids is 80 to 89, and the grid shedding rate is 11% to 20%.

[0179] "Poor": The number of grids is 50 to 79, and the grid shedding rate is 21% to 50%.

[0180] "Poor": the number of grids is 50 or more, and the grid shedding rate is greater than 50%.

[0181] 4. Copper surface oxide layer test

[0182] The photosensitive resin compositions prepared in the above different embodiments were spin-coated onto a copper substrate using a sizing machine (WS-650Mz-8NPPB, MYCRO) and pre-baked on a hot plate at 100°C for 240 seconds to form a coating film of about 15 μm thick. A temperature-programmed curing furnace (HCM-500D, Shanghai Siwang Electronics) was used to heat the film at 350°C for 2 hours under a nitrogen atmosphere to obtain a cured resin film of about 10 μm thick. The coated copper substrate was placed in a high-temperature and high-humidity accelerated aging test chamber (EHS-222MD, ESPEC) under the test conditions of 130°C and 85% RH for 264 hours. After the accelerated aging test, a focused ion beam electron microscope (FIB, Helios G4, Thermo Fisher) was used to slice the joints between the cured resin film and the copper substrate and test the thickness of the copper oxide layer.

[0183] “Optimal”: The oxide layer thickness is less than 50nm, and there are no obvious particles or pores at the interface between the cured resin coating and the copper.

[0184] “Excellent”: The oxide layer thickness is 50-100 nm, and there are no obvious particles or pores at the interface between the cured resin coating and the copper.

[0185] “Excellent”: The oxide layer thickness is 100-500 nm, and there are no obvious particles or pores at the interface between the cured resin coating and the copper.

[0186] “Poor”: The thickness of the oxide layer is 10 to 500 nm, and there are obvious particles and pores at the interface between the cured resin coating and the copper.

[0187] “Poor”: The oxide layer thickness is greater than 500nm, and there are obvious particles and pores at the interface between the cured resin coating and the copper.

[0188] 5. Bottle opening copper surface sealing stability test

[0189] The resin compositions prepared in the above different embodiments were placed at room temperature in an air environment for 30 days, and the adhesion properties of the cured coating film to the copper surface were tested and evaluated again according to the copper surface adhesion test method 30 days after opening the bottle:

[0190] "Optimal": The grid number is 100, 100% no shedding.

[0191] "Excellent": The number of grids is 90-99, and the grid shedding rate is within 10%.

[0192] “Excellent”: The number of grids is 80 to 89, and the grid shedding rate is 11% to 20%.

[0193] "Poor": The number of grids is 50 to 79, and the grid shedding rate is 21% to 50%.

[0194] "Poor": the number of grids is less than 50, and the grid shedding rate is greater than 50%.

[0195] Test results

[0196] The molecular weight of the polyimide precursor A1 (polymer) prepared in Example 3 was measured using an ultra-high performance polymer chromatography (APC) instrument and was found to be: Mw (weight average molecular weight) ranging from 5000 to 30000, and PDI (polydispersity) ranging from 1.5 to 2.5.

[0197] The molecular weight of the polyimide precursor A2 (polymer) prepared in Example 4 was measured using an ultra-high performance polymer chromatography (APC) instrument and was found to be: Mw ranged from 5,000 to 30,000, and PDI ranged from 1.5 to 2.5.

[0198] The molecular weight of the polyimide precursor A3 (polymer) prepared in Example 5 was measured using an ultra-high performance polymer chromatography (APC) instrument and was found to be: Mw ranged from 5,000 to 30,000, and PDI ranged from 1.5 to 2.5.

[0199] The photosensitive resin composition of Example 6 was evaluated according to the above method, and the evaluation results were: "optimal" for photolithography evaluation, "optimal" for copper surface adhesion, "optimal" for copper surface oxidation and porosity, and "excellent" for copper surface open bottle adhesion stability.

[0200] The photosensitive resin composition of Example 7 was evaluated according to the above method, and the evaluation results were: "optimal" for photolithography evaluation, "optimal" for copper surface adhesion, "optimal" for copper surface oxidation and porosity, and "optimal" for copper surface open bottle adhesion stability.

[0201] The photosensitive resin composition of Example 8 was evaluated according to the above method, and the evaluation results were: "optimal" for photolithography evaluation, "optimal" for copper surface adhesion, "excellent" for copper surface oxidation and porosity, and "excellent" for copper surface open bottle adhesion stability.

[0202] The photosensitive resin composition of Example 9 was evaluated according to the above method, and the evaluation results were: "optimal" for photolithography evaluation, "optimal" for copper surface adhesion, "optimal" for copper surface oxidation and porosity, and "optimal" for copper surface open bottle adhesion stability.

[0203] The photosensitive resin composition of Example 10 was evaluated according to the above method, and the evaluation results were: "excellent" in photolithography evaluation, "optimal" in copper surface adhesion performance, "optimal" in copper surface oxidation and porosity, and "excellent" in copper surface open bottle adhesion stability.

[0204] The photosensitive resin composition of Example 11 was evaluated according to the above method, and the evaluation results were: "excellent" in photolithography evaluation, "optimal" in copper surface adhesion performance, "optimal" in copper surface oxidation and porosity, and "optimal" in copper surface open bottle adhesion stability.

[0205] The photosensitive resin composition of Example 12 was evaluated according to the above method, and the evaluation results were: "excellent" in photolithography evaluation, "optimal" in copper surface adhesion performance, "excellent" in copper surface oxidation and porosity, and "excellent" in copper surface open bottle adhesion stability.

[0206] The photosensitive resin composition in Example 13 was evaluated according to the above method, and the evaluation results were: "excellent" in photolithography evaluation, "optimal" in copper surface adhesion performance, "optimal" in copper surface oxidation and porosity, and "optimal" in copper surface open bottle adhesion stability.

[0207] The photosensitive resin composition in Comparative Example 1 was evaluated according to the above method, and the evaluation results were: "excellent" in photolithography evaluation, "poor" in copper surface adhesion, "poor" in copper surface oxidation and porosity, and "poor" in copper surface open bottle adhesion stability.

[0208] The photosensitive resin composition in Comparative Example 2 was evaluated according to the above method, and the evaluation results were: "optimal" in photolithography evaluation, "optimal" in copper surface adhesion performance, "relatively good" in copper surface oxidation and porosity, and "relatively poor" in copper surface bottle opening adhesion stability.

[0209] The photosensitive resin composition in Comparative Example 3 was evaluated according to the above method, and the evaluation results were: "excellent" in photolithography evaluation, "poor" in copper surface adhesion, "poor" in copper surface oxidation and porosity, and "poor" in copper surface open bottle adhesion stability.

[0210] The photosensitive resin composition in Comparative Example 4 was evaluated according to the above method, and the evaluation results were: "optimal" in photolithography evaluation, "poor" in copper surface adhesion, "poor" in copper surface oxidation and porosity, and "poor" in copper surface open bottle adhesion stability.

[0211] The photosensitive resin composition in Comparative Example 5 was evaluated according to the above method, and the evaluation results were: "optimal" in photolithography evaluation, "good" in copper surface adhesion, "poor" in copper surface oxidation and porosity, and "poor" in copper surface bottle opening adhesion stability.

[0212] The evaluation results of the photosensitive resin compositions in Examples 6 to 13 and Comparative Examples 1 to 5 are shown in Table 1 below.

[0213] Table 1 - Evaluation results of the photosensitive resin compositions in Examples 6 to 13 and Comparative Examples 1 to 5

[0214] As can be seen from Table 1, the photosensitive resin composition prepared in the examples of the present application can improve the bonding strength between PSPI and the copper surface, inhibit the formation of pores and oxide layer particles at the interface between PSPI and copper, and at the same time improve the bottle opening stability that optimizes the bonding strength to the copper surface.

[0215] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention should be included in the scope of protection of the present invention.

Claims

1. A tetrazolyl silane coupling agent, characterized in that: The structural formula of the tetrazolyl silane coupling agent is as shown in the following formula (Ⅰ) or (Ⅱ); Wherein, R1, R2, and R3 are each independently selected from any one of a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or an aromatic group; R4 is selected from any one of a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, an amino group, an alkyl group having 1 to 10 carbon atoms, or an aromatic group; R5 is selected from any one of a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, an amino group, an alkyl group having 1 to 10 carbon atoms, or an aromatic group; n is a positive integer between 1 and 20.

2. The tetrazolyl silane coupling agent according to claim 1, characterized in that: The structural formula of the tetrazolyl silane coupling agent includes any one of the following formulas; 3. A method for preparing a tetrazolyl silane coupling agent as claimed in claim 1, characterized in that: The following steps are involved: The first compound and the third compound are subjected to an amidation reaction to obtain a tetrazolyl silane coupling agent represented by formula (I); The second compound and the third compound are subjected to an imidization reaction to obtain a tetrazolyl silane coupling agent represented by formula (II); Wherein, the structural formula of the first compound is: The structural formula of the second compound is: The structural formula of the third compound is:

4. The method for preparing a tetrazolyl silane coupling agent according to claim 3, wherein: The first compound or the second compound is added to the first organic solvent, and then the third compound is added, reacted at 45-55°C for 2-3 hours, cooled to room temperature, and then pyridine is added. After stirring, acetic anhydride is added, and the reaction is carried out at room temperature for 18-22 hours. After the amidation reaction is completed, the tetrazolyl silane coupling agent is obtained by vacuum distillation.

5. The method for preparing a tetrazolyl silane coupling agent according to claim 4, wherein: The first compound is 1-aminotetrazolyl, the second compound is 5-aminotetrazolyl, and the third compound is 3-(triethoxysilyl)propyl succinic anhydride or [3-(trimethoxysilyl)propyl]succinic anhydride; The first organic solvent includes one or more of N-methylpyrrolidone, dimethyl sulfoxide, and N,N-dimethylacetamide; The molar ratio of the first compound or the second compound, the third compound, pyridine and acetic anhydride is (0.05-0.15):(0.05-0.15):(0.1-0.3):(0.1-0.3); The molar volume ratio of the first compound or the second compound to the first organic solvent is (0.05-0.15) mol: (200-300) mL.

6. A photosensitive resin composition, characterized in that: The invention comprises the tetrazolyl silane coupling agent as claimed in any one of claims 1 to 2, a polyimide precursor and a photopolymerization initiator.

7. A photosensitive resin composition according to claim 6, characterized in that: The structural formula of the polyimide precursor is: Wherein, R6 is a tetravalent organic group having 6 to 50 carbon atoms; R7 is a divalent organic group having 6 to 50 carbon atoms; R8 and R9 are each independently selected from any one of a hydrogen atom, an organic group having 2 to 30 carbon atoms and at least one free radical polymerizable unsaturated bond group, and a saturated aliphatic group having 1 to 10 carbon atoms; n1 is a positive integer between 1 and 1000; And / or, the photopolymerization initiator is an oxime ester photoinitiator; And / or, the mass ratio of the polyimide precursor, tetrazolyl silane coupling agent and photopolymerization initiator is It is 100:(0.1~20):(0.5~50). And / or, the quaternary organic group includes any one of 4,4'-oxydiphthalic anhydride and pyromellitic dianhydride; And / or, the divalent organic group includes any one of 4,4'-diaminodiphenyl ether and p-phenylenediamine; And / or, the organic group having at least one free radical polymerizable unsaturated bond group includes any one of a hydroxyl group, an acrylic group, and a methacrylic group.

8. A method for preparing a photosensitive resin composition according to any one of claims 6 to 7, characterized in that: The following steps are involved: A tetrazolyl silane coupling agent, a polyimide precursor and a photopolymerization initiator are added into the second solvent to obtain a photosensitive resin composition.

9. The method for preparing the photosensitive resin composition according to claim 8, wherein: Adding a tetrazolyl silane coupling agent, a polyimide precursor, a photopolymerization initiator, and a photocrosslinking agent into the second solvent, and adjusting the viscosity of the system to 25 to 35 poise, to obtain a photosensitive resin composition; The second solvent includes one or more of N-methylpyrrolidone, dimethyl sulfoxide, N,N-dimethylacetamide, and γ-butyrolactone; The mass ratio of the polyimide precursor, tetrazolyl silane coupling agent, photopolymerization initiator and photocrosslinking agent is 100:(0.1-20):(0.5-50):(5-15); And / or, the preparation method of the polyimide precursor comprises the following steps: Adding 4,4'-oxydiphthalic anhydride or pyromellitic dianhydride to the third solvent, and then adding hydroxyethyl methacrylate and pyridine, and reacting to obtain a first mixture; adding dicyclohexylcarbodiimide to the first mixture and continuing the reaction to obtain a second mixture; Adding 4,4'-diaminodiphenyl ether or p-phenylenediamine to the second mixture to obtain a polyimide precursor through reaction; The mass ratio of the 4,4'-oxydiphthalic anhydride or pyromellitic anhydride, hydroxyethyl methacrylate, pyridine, dicyclohexylcarbodiimide, 4,4'-diaminodiphenyl ether or p-phenylenediamine is (70-120):(70-100):(2-6):(120-150):(30-80).

10. Use of the photosensitive resin composition according to any one of claims 6 to 7 or the photosensitive resin composition prepared by the preparation method according to any one of claims 8 to 9 in wafer-level packaging rewiring process, circuit packaging of structural devices, insulation protection of semiconductor components, and insulation buffering of OLED components.

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