A low-temperature curing photosensitive resin composition, a preparation method and applications thereof
A photosensitive resin composition copolymerized with alkali-soluble resin and organosilane in a specific ratio solves the problems of poor adhesion, poor chemical resistance and poor coating performance in flexible display panels, and achieves uniform film thickness and flexibility under low temperature curing, making it suitable for flexible electronic devices.
Patent Information
- Application Number
- CN202211583648.7
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2022-12-10
- Publication Date
- 2026-01-23
- Estimated Expiration
- 2042-12-10
AI Technical Summary
Existing photosensitive resin compositions suffer from poor adhesion, poor chemical resistance, poor coating performance, and uneven display in flexible display panels, especially at low temperatures where they fail to meet the requirements of flexible electronic devices.
A specific ratio of alkali-soluble resin, photopolymerizable monomer, photoinitiator and solvent is used to mix the alkali-soluble resin, which is a copolymer of oligomers with aromatic ring main chains and organosilane oligomers. Leveling agents, defoamers and ultraviolet absorbers are added, and a photocurable pattern is formed through a low-temperature curing process.
Excellent adhesion, film thickness uniformity, and flexibility of the photosensitive resin composition to the substrate were achieved under low-temperature conditions, eliminating the mura phenomenon and ensuring the stability and chemical resistance of the flexible display panel.
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Abstract
Description
TECHNICAL FIELD
[0001] The present application belongs to the technical field of photosensitive resin, and relates to a low-temperature curing type photosensitive resin composition, a preparation method and application thereof. BACKGROUND
[0002] In the preparation process of electronic devices (such as display panels and touch panels), various photosensitive resin compositions such as positive or negative types are generally used as materials, and the photosensitive properties thereof are utilized to pattern and cure the resin compositions to form members such as passivation layers, protective layers or insulating layers.
[0003] In recent years, with the continuous development of flexible display panels, various materials for flexible panels are continuously developed. In the preparation process of flexible display panels, in order to enable the photosensitive resin composition to have better adhesion and chemical resistance, the photosensitive resin composition needs to be subjected to a post-baking procedure at high temperature. However, at high temperature, the stability of other materials in the flexible display panel cannot be guaranteed. Therefore, the photosensitive resin composition needs to have excellent adhesion to the substrate and excellent chemical resistance to chemical treatments used in subsequent processes even under mild conditions (150°C). In addition, in the current low-temperature curing photosensitive resin composition, the problem of poor flexibility often exists, and the photosensitive resin composition cannot be applied to flexible electronic devices. On the other hand, in the manufacture of flat panel displays in recent years, large-size panels such as 1100 mm x 1250 mm are used, and thus problems such as poor coating performance, mura and the like exist, resulting in the problem of display unevenness on the flexible display panel.
[0004] Patent application JP2016204585A discloses a photosensitive resin composition applied to a low-temperature process, but the photosensitive resin composition after curing has high hardness, and thus cannot meet the application in flexible electronic products.
[0005] Patent application CN108931885B discloses a low-temperature curing photosensitive resin composition. The film formed by the photosensitive resin in this patent has excellent adhesion, reliability and flexibility, and thus can be applied to flexible devices. However, the patent does not take into account the problems of poor coating performance, mura and the like when the photosensitive resin is applied to large-size display panels. SUMMARY
[0006] The present application aims to overcome the shortcomings of the prior art, and provides a low-temperature curing type photosensitive resin composition, a preparation method and application thereof. The adhesion of the photosensitive resin composition to the substrate under mild conditions is poor, the chemical resistance is not good, and the problems of display unevenness on the display panel due to poor coating performance, mura and the like are solved.
[0007] In order to achieve the above object, the present application adopts the following technical solutions:
[0008] A low-temperature curing type photosensitive resin composition, comprising an alkali-soluble resin, a photopolymerization monomer, a photoinitiator and a solvent; the mass ratio of the alkali-soluble resin, the photopolymerization monomer, the photoinitiator and the solvent is (5-15):(5-20):(1-10):(60-80).
[0009] Further, the alkali-soluble resin is copolymerized from an oligomer with an aromatic ring main chain and an organosilane type oligomer, and the molar ratio of the oligomer with an aromatic ring main chain and the organosilane type oligomer is 1:(0.5-1.5).
[0010] Further, the alkali-soluble resin is represented by formula 1:
[0011]
[0012] wherein p, q are each independently an integer of 0-20; X1, X2, X3, X4 are each independently any one of hydrogen, a substituted or unsubstituted C1-C20 alkyl, a substituted or unsubstituted C1-C20 alkoxy, a substituted or unsubstituted C3-C20 cycloalkyl, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C7-C30 aralkyl;
[0013] Ar1, Ar2 represent the same structural formula, which is any one of formula 2-formula 5, and the structural formula of formula 2-formula 5 is as follows:
[0014]
[0015] wherein * is a binding site;
[0016] L1-L9 are represented by formula 6:
[0017]
[0018] wherein * represents a binding site, Z1 is any one of a C1-C20 branched or straight chain alkylene substituted with a hydroxyl group or not, a substituted or unsubstituted C1-C20 branched or straight chain alkoxy; R1 is hydrogen or methyl.
[0019] Further, the structure of the alkali-soluble resin is any one of the following:
[0020]
[0021]
[0022] wherein p1-p4, q1-q4 are each independently an integer of 0-20.
[0023] The term "substituted" means that at least one hydrogen atom of a functional group is replaced by a halogen (F, Cl, Br, or I), a hydroxyl group, an imino group, a C1 to C20 alkyl group, a C6 to C30 aryl group.
[0024] The term "alkyl" means a monovalent group of an alkane, which is a saturated hydrocarbon. The alkyl group can be linear, branched, cyclic, or a combination thereof; the term "alkylene" means a divalent group of an alkane group. The alkylene group can be linear, branched, cyclic, or a combination thereof; the term "alkyleneoxy" can include all functional groups of one or more alkylene groups linked with at least one oxygen. For example, it can include -(alkylene-oxygen) n -alkylene-, -(alkylene-oxygen-alkylene) n -alkylene-, -alkylene-oxygen-, or -(oxygen-alkylene) n - wherein n is an integer from 1 to 10.
[0025] Further, the photopolymerization monomer is one or more of trimethylolpropane tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, propoxylated trimethylolpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, polydipentaerythritol penta(meth)acrylate, sorbitol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate.
[0026] The term "monofunctional" monomer means a monomer containing one photocurable functional group; "difunctional" monomer means a monomer containing two photocurable functional groups, and "polyfunctional" monomer means a monomer containing three or more photocurable functional groups.
[0027] Further, the photopolymerization monomer is one or more of trimethylolpropane tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, propoxylated trimethylolpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, polydipentaerythritol penta(meth)acrylate, sorbitol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate.
[0028] Further, the photoinitiator is one or more of an ethanone-based compound, a benzophenone-based compound, a triazine-based compound, a bisimidazole-based compound, a thioxanthone-based compound, and an oxime ester-based compound.
[0029] Further preferably, the photoinitiator is an oxime ester-based compound.
[0030] Further, the solvent is one or more of a fatty alcohol, ethyl lactate, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, ethylene glycol dimethyl ether, methyl isobutyl ketone, propylene glycol monomethyl ether, propylene glycol methyl ether acetate.
[0031] Further preferably, the solvent is propylene glycol methyl ether acetate and / or ethyl lactate.
[0032] Further, the low-temperature curing type photosensitive resin composition can further include an additive in an amount of 0.1 to 5% by mass based on the total mass of the low-temperature curing type photosensitive resin composition. Specifically, the additive can include at least one of a polymerization inhibitor, a leveling agent, a defoaming agent, and an ultraviolet absorber.
[0033] Further preferably, the additive is a mixture of a polymerization inhibitor, a leveling agent, a defoaming agent, and an ultraviolet absorber.
[0034] Specifically, the polymerization inhibitor includes one or a mixture of several of hydroquinone, 2-sec-butyl-4,6-dinitrophenol, p-tert-butyl hydroquinone, 2,5-di-tert-butyl hydroquinone; and the polymerization inhibitor is included in an amount of 0.01 to 1% by mass based on the total mass of the photosensitive resin composition.
[0035] Specifically, the leveling agent is a non-ionic siloxane copolymer, which can be purchased from Troysol S366.
[0036] Further, the leveling agent is included in an amount of 0.1 to 0.5% by mass based on the total mass of the photosensitive resin composition. The present application is advantageous in promoting the improvement of substrate wetting, surface flow, and leveling by adding the leveling agent of the non-ionic siloxane copolymer.
[0037] Specifically, the defoaming agent is a modified silicone polydimethylsiloxane and / or organosilicon, which can be purchased from BYK-019; and the defoaming agent is included in an amount of 0.01 to 1% by mass in the photosensitive resin composition.
[0038] Specifically, the ultraviolet absorber includes one or a mixture of several of benzotriazole-based, including 2-(2'-hydroxy-5'-methylphenyl) benzotriazole (UV-P), 2-(2'-hydroxy-5'-tert-octylphenyl) benzotriazole (UV-329), 2-phenylbenzimidazole-5-sulfonic acid (UV-T), 2-(2H-benzotriazol-2-yl)-4,6-di-tert-amylphenol (UV-328), 2-benzotriazol-2-yl-4,6-bis-tert-butylphenol (UV-320); and the ultraviolet absorber is included in an amount of 0.5 to 3% by mass based on the total mass of the photosensitive resin composition.
[0039] A method for preparing a low-temperature curing type photosensitive resin composition, the method being mixing an alkali-soluble resin, a photopolymerization monomer, a photoinitiator, a solvent, and an additive uniformly, filtering, and obtaining the low-temperature curing type photosensitive resin composition.
[0040] An application of a low-temperature curing type photosensitive resin composition, the low-temperature curing type photosensitive resin composition being applied to a low-temperature curing process, and the low-temperature curing process requiring a temperature of 70 to 100°C.
[0041] The prepared low-temperature curing type photosensitive resin composition of the present application can be used to form a photocured pattern; the photocured pattern can be prepared by coating the above-mentioned low-temperature curing type photosensitive resin composition on a substrate, and then exposing and developing; specifically: the low-temperature curing type photosensitive resin composition of the present application is coated on a substrate, and then heated and dried or heated and dried under reduced pressure to remove volatile components such as solvents, to obtain a smooth coating film, then the obtained coating film is irradiated with ultraviolet rays through a mask, and then developed with a developing solution, thereby forming a desired photocured pattern; the thickness of the photocured pattern is 1-8 μm.
[0042] Further, the ultraviolet rays can use g-rays (wavelength: 436 nm), h-rays (wavelength: 405 nm), i-rays (wavelength: 365 nm); preferably i-rays (wavelength: 365 nm).
[0043] Further, the developing solution is an aqueous solution of alkali or a mixed aqueous solution of alkali and a surfactant;
[0044] Specifically, the alkali can be inorganic alkali (sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, ammonia water, etc.), primary amine (ethylamine, n-propylamine, etc.), secondary amine (diethylamine, di-n-butylamine, etc.), tertiary amine (triethylamine, methyldiethylamine, etc.), alcohol amine (dimethyl ethanolamine, triethanolamine, etc.), quaternary ammonium salt (tetramethylammonium hydroxide, tetraethylammonium hydroxide, choline hydroxide, etc.), cyclic amine (pyrrole, piperidine, etc.).
[0045] Compared with the prior art, the present application has the following beneficial effects:
[0046] 1. The present application fully utilizes the functions of each functional group by using the alkali-soluble resin copolymerized from the oligomer with aromatic ring main chain and the organosilane oligomer with a molar ratio of 1:(0.5-1.5), so that the prepared low-temperature curing type photosensitive resin composition has excellent leveling property, the cured photosensitive resin composition film has good thickness uniformity, no mura and no bubbles, at the same time, has excellent adhesion when forming a coating film on a substrate, the adhesion can reach 5B, and has excellent chemical resistance to chemical treatment after development.
[0047] 2. The prepared photosensitive resin composition can be used in low-temperature curing process, which can be fully cured below 100℃, can effectively reduce the post-baking temperature in the photocured pattern preparation process, and the cured photosensitive resin composition film has excellent flexibility, which can be applied in flexible electronic products, and ensures the stability of other materials in the flexible display panel. DETAILED DESCRIPTION
[0048] The exemplary embodiments will be described in detail below with reference to the drawings. The embodiments described in the following exemplary embodiments do not represent all the embodiments consistent with the present application. Rather, they are merely examples of apparatuses consistent with some aspects of the present application as detailed in the appended claims.
[0049] In order for those skilled in the art to better understand the technical solutions of the present application, the present application will be described in further detail below with reference to the accompanying drawings and examples.
[0050] The base-soluble resin used in the following examples has the structure of Formula 1-1, with the difference being the difference between P1 and P2.
[0051] Preparation Example 1
[0052] The synthetic route of the base-soluble resin A1 is as follows:
[0053]
[0054] A 250 mL three-necked flask was charged with 25.00 g (10 mmol) of resin A (Hebei Ruiqi Technology Co., Ltd.), heated to 120°C, and then 7.8 g (10 mmol) of organosilane oligomer B (Dongguan Shin-Etsu Electronic Materials Co., Ltd.) was added under nitrogen protection. Subsequently, 0.125 g of dibutyltin dilaurate was added as a catalyst, and the flask was heated until all the resin was melted, and then reacted at 120°C for 2 hours. Then, the temperature was cooled to 70°C, 7.83 mL (100 mmol) of epichlorohydrin, 0.645 g (2 mmol) of tetra-t-butylammonium bromide, and 1.6 mL of NaOH aqueous solution (50 wt%) were added. The reaction mixture was stirred at 70°C for 4 hours, and then cooled to room temperature. The excess epichlorohydrin and solvent were evaporated, and the remaining material was washed with water to obtain a white solid substance. The obtained resin was recrystallized with ethanol and acetone to obtain resin C, and the epoxy equivalent weight of the epoxy resin was determined to be 184-195.
[0055] A 250 mL three-necked flask was charged with 25.00 g (10 mmol) of resin A (Hebei Ruiqi Technology Co., Ltd.), heated to 120°C, and then 7.8 g (10 mmol) of organosilane oligomer B (Dongguan Shin-Etsu Electronic Materials Co., Ltd.) was added under nitrogen protection. Subsequently, 0.125 g of dibutyltin dilaurate was added as a catalyst, and the flask was heated until all the resin was melted, and then reacted at 120°C for 2 hours. Then, the temperature was cooled to 70°C, 7.83 mL (100 mmol) of epichlorohydrin, 0.645 g (2 mmol) of tetra-t-butylammonium bromide, and 1.6 mL of NaOH aqueous solution (50 wt%) were added. The reaction mixture was stirred at 70°C for 4 hours, and then cooled to room temperature. The excess epichlorohydrin and solvent were evaporated, and the remaining material was washed with water to obtain a white solid substance. The obtained resin was recrystallized with ethanol and acetone to obtain resin C, and the epoxy equivalent weight of the epoxy resin was determined to be 184-195.
[0056] Preparation Example 2
[0057] Synthesis of base-soluble resin A2:
[0058] A (Hebei Ruiqi Technology Co., Ltd.) was charged into a 250 mL three-necked flask, then heated to 120°C, followed by adding 15.6 g (20 mmol) of organosilane oligomer B (Dongguan Shin-Etsu Electronic Materials Co., Ltd.) under nitrogen protection. Subsequently, 0.125 g of dibutyltin dilaurate was added as a catalyst into the flask, heated to all the resin was melted, and reacted at 120°C for 2 hours. Then cooled to 70°C, 7.83 mL (100 mmol) of epichlorohydrin, 0.645 g (2 mmol) of tetra-t-butyl ammonium bromide and 1.6 mL of NaOH aqueous solution (50 wt%) were added. The reaction mixture was stirred at 70°C for 4 hours, and cooled to room temperature. The excess epichlorohydrin and solvent were evaporated, and the remaining material was washed with water to obtain a white solid material. The obtained resin was recrystallized with ethanol and acetone to obtain resin C, and the epoxy equivalent weight of the epoxy resin was determined to be 184-195.
[0059] A 250 mL three-necked flask equipped with a magnetic stirrer, a condenser, a nitrogen protection device and a thermometer was charged with 25 g of resin C, 100 mL of toluene, followed by adding 0.05 g of 2,6-di-t-butyl-p-cresol and 0.05 g of triphenylphosphine catalyst, and then 9.71 g of acrylic acid was added dropwise. The reaction was carried out at 80-90°C until the acid value was less than 3 mgKOH / g, and then the reaction was stopped. The reaction liquid was cooled to 50°C, and then distilled under reduced pressure until no liquid dropped out. Then, the reaction liquid was distilled under reduced pressure at 60°C for more than 2 hours until no liquid dropped out, and a colorless transparent liquid was obtained, which was the alkali-soluble resin A1.
[0060] The details of the components used in the following test procedures for the examples and comparative examples are shown as follows:
[0061] (A) Alkali-soluble resin: A1 is the resin obtained in Preparation Example 1; A2 is the resin obtained in Preparation Example 2.
[0062] (B) Photopolymerization monomer: B1 is pentaerythritol triacrylate (PETA); B2 is
[0063] pentaerythritol tetraacrylate (PETTA);
[0064] (C) Photoinitiator: oxime ester photopolymerization initiator OXE-01 (BASF);
[0065] (D) Solvent: propylene glycol methyl ether acetate;
[0066] (E) Polymerization inhibitor: hydroquinone;
[0067] (F) Ultraviolet absorber: UV320 (BASF);
[0068] (G) Defoaming agent: BYK-019;
[0069] (H) Leveling agent: Troysol S366 by Troika
[0070] Example 1
[0071] The low temperature curing type photosensitive resin composition of this example is composed of 10 g of alkali-soluble resin, 10 g of pentaerythritol triacrylate, 5 g of pentaerythritol tetraacrylate, 2.5 g of oxime ester-based photopolymerization initiator OXE-01, 70 g of propylene glycol methyl ether acetate, 0.5 g of hydroquinone, 2 g of ultraviolet absorber UV320, 0.2 g of defoaming agent BYK-019, and 0.05 g of Troysol S366 by Troika; the alkali-soluble resin is the alkali-soluble resin Al obtained in Preparation Example 1.
[0072] The preparation method of the low temperature curing type photosensitive resin composition is to mix and dissolve the above components, and then filter through a filter core of 0.2 μm to obtain the low temperature curing type photosensitive resin composition.
[0073] Example 2
[0074] The low temperature curing type photosensitive resin composition of this example is composed of 15 g of alkali-soluble resin, 10 g of pentaerythritol triacrylate, 10 g of pentaerythritol tetraacrylate, 5 g of oxime ester-based photopolymerization initiator OXE-01, 80 g of propylene glycol methyl ether acetate, 1 g of hydroquinone, 2 g of ultraviolet absorber UV320, 0.3 g of defoaming agent BYK-019, and 0.04 g of Troysol S366 by Troika; the alkali-soluble resin Al is the resin obtained in Preparation Example 1.
[0075] The preparation method of the low temperature curing type photosensitive resin composition is to mix and dissolve the above components, and then filter through a filter core of 0.2 μm to obtain the low temperature curing type photosensitive resin composition.
[0076] Example 3
[0077] The low temperature curing type photosensitive resin composition of this example is composed of 5 g of alkali-soluble resin, 15 g of pentaerythritol tetraacrylate, 5 g of oxime ester-based photopolymerization initiator OXE-01, 60 g of propylene glycol methyl ether acetate, 1 g of hydroquinone, 2 g of ultraviolet absorber UV320, 0.2 g of defoaming agent BYK-019, and 0.02 g of Troysol S366 by Troika; the alkali-soluble resin is the alkali-soluble resin Al obtained in Preparation Example 1.
[0078] The preparation method of the low temperature curing type photosensitive resin composition is to mix and dissolve the above components, and then filter through a filter core of 0.2 μm to obtain the low temperature curing type photosensitive resin composition.
[0079] Comparative Example 1
[0080] The specific implementation method of Comparative Example 1 is the same as that of Example 1, except that the amount of alkali-soluble resin added in Comparative Example 1 is 70g.
[0081] Comparative Example 2
[0082] The specific implementation of Comparative Example 2 is the same as that of Example 1, except that: in Comparative Example 2, the alkali-soluble resin is resin A2 obtained in Preparation Example 2, wherein the molar ratio of oligomer with aromatic ring main chain to organosilanes oligomer is 1:2.
[0083] Performance testing:
[0084] Prepare a 10cm × 10cm × 0.7mm glass substrate, clean it with deionized water and acetone, and then spin-coat the photosensitive resin compositions obtained in the examples and comparative examples onto the glass substrate. Control the spin speed to achieve a thickness of 2μm for the photosensitive resin composition, and then bake it at 80℃ for 5 minutes. Using a mask with a line / gap pattern of 1–50μm, employ an i-line stepper (wavelength: 365nm) at an exposure dose of 70mJ / cm². 2 The photosensitive resin composition coated on the surface of the glass substrate was exposed, then developed with alkaline developer, and the residual developer was washed away with water. Finally, the developed glass was baked at 80°C for 60 minutes to obtain the sample.
[0085] (1) Adhesion test: The test was conducted according to GB9286-1998 "Cross-cut test for paint and varnish film". The coating was cut into 10*10 (100) small grids using a cross-cut tester. 3M transparent tape was attached to the cut grids and force was applied to ensure that the tape was firmly attached to the coating surface and the cut grid areas. Within 1 to 2 minutes, one end of the 3M tape was held and peeled off smoothly at a 60-degree angle within 0.5 to 1 second. The degree and extent of coating peeling on the substrate were visually observed to determine its ASTM rating.
[0086] Specifically, the ASTM grades are as follows: 5B - Smooth cut edges with no peeling at the grid edges; 4B - Peeling area within the grid area ≤ 5%; 3B - Peeling area within the grid area > 5% to 15%; 2B - Peeling area within the grid area > 15% to 35%; 1B - Peeling area within the grid area > 35% to 65%; 0B - Peeling area within the grid area > 65%.
[0087] (2) Thickness uniformity test: The thickness deviation of the cured photosensitive resin composition was tested using a film thickness gauge; U% = (maximum value - minimum value) / 2 times the average value.
[0088] (3) Chemical resistance: The sample obtained above was immersed in an organic stripping agent solution and treated at 60°C for 2 min. The thickness of the film was measured and the chemical resistance was evaluated based on the following criteria.
[0089] ○ indicates that the change in film thickness before and after peeling is less than 4%;
[0090] △ indicates that the film thickness changed by 4-8% before and after peeling;
[0091] × indicates that the film thickness changed by more than 8% before and after peeling.
[0092] (4) Mura test: Irradiate the coated surface with a sodium lamp to check for uneven brightness and bubbles.
[0093] ○ indicates uniform brightness and no bubbles;
[0094] ● Indicates uneven brightness, but no bubbles;
[0095] ▲ indicates uniform brightness with bubbles;
[0096] × indicates uneven brightness or the presence of air bubbles;
[0097] (5) Flexibility test: The film obtained by the cured low-temperature curing photosensitive resin composition is subjected to a bending test. The bending rate of the bending test is 180 degrees and the bending radius is 1 cm. Observe whether cracks are generated.
[0098] ○ indicates that there is no crack.
[0099] × indicates that there is a crack.
[0100] The performance test results of the photosensitive resin compositions in each embodiment and comparative example are shown in Table 1 below:
[0101] Table 1.
[0102]
[0103]
[0104] As shown in Table 1, the low-temperature curing photosensitive resin prepared by the present invention has excellent adhesion, film thickness uniformity, chemical resistance and flexibility, and eliminates mura, thereby ensuring the stability of other materials in the flexible display panel.
[0105] Conversely, Comparative Example 1 showed poorer overall performance compared to Example 1, demonstrating that when the mass ratio of alkali-soluble resin, photopolymerizable monomer, photoinitiator, and solvent is (5-15):(5-20):(1-10):(60-80), the performance of its low-temperature curable photosensitive resin is better.
[0106] Compared to Example 1, Comparative Example 2 showed poorer overall performance, demonstrating that when the molar ratio of oligomers with aromatic ring backbones to organosilanes is 1:(0.5-1.5), the performance of its low-temperature curable photosensitive resin is better.
[0107] The above description is merely a specific embodiment of the present invention, enabling those skilled in the art to understand or implement the invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the general principles defined herein may be implemented in other embodiments without departing from the spirit or scope of the invention.
[0108] It should be understood that the present invention is not limited to the content already described above, and various modifications and changes can be made without departing from its scope. The scope of the present invention is limited only by the appended claims.
Claims
1. A low-temperature curing photosensitive resin composition, characterized in that, It includes an alkali-soluble resin, a photopolymerizable monomer, a photoinitiator, and a solvent; the alkali-soluble resin is copolymerized from an oligomer with an aromatic ring backbone and an organosilane oligomer, wherein the molar ratio of the oligomer with the aromatic ring backbone to the organosilane oligomer is 1:(0.5~1.5). The alkali-soluble resin is represented by Formula 1: Formula 1 Wherein, p and q are each independently an integer from 0 to 20; X1, X2, X3, and X4 are each independently hydrogen, any one of substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C7-C30 aralkyl. Ar1 and Ar2 represent the same structural formula, which is any one of Equations 2-5. The structural formulas of Equations 2-5 are as follows: Formula 2 Formula 3 Formula 4 Formula 5 Where * represents a binding site; L1 - L9 is represented by Equation 6: Formula 6 Wherein, * indicates the binding position, and Z1 is a C1-C20 branched or straight chain that is hydroxylated or unsubstituted. R1 is any one of alkylene, substituted or unsubstituted C1-C20 branched or straight-chain alkene; R1 is hydrogen or methyl.
2. The low-temperature curing photosensitive resin composition according to claim 1, characterized in that, The structure of the alkali-soluble resin is any one of the following: Equation 1-1 Formula 1-2 Formula 1-3 Formula 1-4 Among them, p1-p4 and q1-q4 are each independent integers from 0 to 20.
3. The low-temperature curing photosensitive resin composition according to claim 1, characterized in that, The mass ratio of the alkali-soluble resin, photopolymerizable monomer, photoinitiator and solvent is (5~15):(5~20):(1~10):(60~80).
4. The low-temperature curing photosensitive resin composition according to claim 1, characterized in that, The photopolymerizable monomer is a multifunctional (meth)acrylate.
5. The low-temperature curing photosensitive resin composition according to claim 1, characterized in that, The photoinitiator is one or more of the following: acetone compounds, benzophenone compounds, triazine compounds, biimidazole compounds, thioxanone compounds, and oxime ester compounds.
6. The low-temperature curing photosensitive resin composition according to claim 1, characterized in that, The solvent is one or more of the following: fatty alcohol, ethyl lactate, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, ethylene glycol dimethyl ether, methyl isobutyl ketone, propylene glycol monomethyl ether, and propylene glycol methyl ether acetate.
7. The low-temperature curing photosensitive resin composition according to claim 1, characterized in that, It also includes additives, which account for 0.1 to 5% of the total mass of the low-temperature curing photosensitive resin composition.
8. A method for preparing a low-temperature curable photosensitive resin composition according to any one of claims 1-7, characterized in that, The method involves mixing alkali-soluble resin, photopolymerizable monomer, photoinitiator, solvent, and additives evenly, and then filtering to obtain a low-temperature curing photosensitive resin composition.
9. The application of a low-temperature curing photosensitive resin composition according to any one of claims 1-7, characterized in that, The low-temperature curing photosensitive resin composition is used in a low-temperature curing process, wherein the required temperature in the low-temperature curing process is 70~100℃.
Citation Information
Patent Citations
Low-temperature curing photosensitive resin compositions and their uses
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Curable composition, cured film, organic el display device, liquid crystal display device, touch panel and touch panel display device
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Photosensitive resin composition, black matrix and display device
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