A resin, a photosensitive resin composition, and applications thereof

Abstract

The present application provides a resin, a photosensitive resin composition and application thereof, the resin has a structure as shown in formula I, the resin structure of the present application is connected with a chalcone structure capable of playing a role of ultraviolet absorber, and is also connected with a hindered amine structure capable of playing a role of light stability, and the resin has a double bond and a carboxyl group, can be polymerized and developed, is applied to a photosensitive resin composition, and can be used to prepare an optical film capable of playing a role of anti-reflection, and the film layer has excellent reliability performance.

Description

TECHNICAL FIELD

[0001] The present application belongs to the technical field of photosensitive materials, and relates to a resin, a photosensitive resin composition and application thereof. BACKGROUND

[0002] An organic light emitting diode (OLED) display is different from a liquid crystal display device, does not need a backlight, adopts a very thin organic material coating and a glass substrate (or a flexible organic substrate), and forms electrodes or wiring made of metal in the area of a display surface of a self-luminous display device. The material is lighter and thinner, can be transparent and flexible, has excellent color saturation, contrast and response speed, can realize diversified design, and meets new requirements of consumers on display technology. However, the electrodes or wiring made of metal reflect light (that is, external light) from the outside of the display picture, causing a mixed reflection image and a display image, which can cause a decrease in display quality such as a decrease in contrast. Therefore, the OLED display device needs to be endowed with an anti-reflection function, and further requirements on reliability of the anti-reflection film are put forward to improve display quality.

[0003] In order to solve the above problems, a screen lamination technology (COE) is used to replace a traditional core material polarizing sheet to improve light transmittance, improve color reproduction, and reduce panel power consumption. The lamination structure is composed of a black matrix or a pixel definition layer and R, G and B color films. In order to further improve color reproduction, the color film often needs to be thickened and the color material needs to be highly concentrated, which causes problems such as deterioration of pixel shape and viewing angle characteristics, and thus the display quality is decreased. In addition, the lamination structure has a complex forming process, and has a problem of cost increase.

[0004] In order to reduce the cost, according to this structure, while the reflection of external light is inhibited and the visibility is improved, the color purity is also improved because the light in the wavelength band that particularly reduces the color purity of the light emitted from the display device is selectively absorbed. However, in the disclosed technology, there are problems of insufficient reflection inhibition of external light and coloring of reflected light. In addition, the reliability such as light resistance of the color material that absorbs light of a specific wavelength is insufficient, and practicalization is difficult (see Japanese Patent No. 5673713).

[0005] To further solve the above problems, CN116848441A and CN116997828A adopt a method of adding an ultraviolet absorbing layer and other functional layers on the device coloring layer, which has a complex process, involves many materials, and has high cost. CN117677870A provides an optical film with low reflection, brightness efficiency and reliability by using black organic pigments in the coloring layer. However, this method needs to strictly control the proportion between the color materials, otherwise it will cause a decrease in display quality.

[0006] Therefore, it is desirable to develop an optical material with high brightness efficiency, anti-reflection, and good reliability without additional preparation of an ultraviolet absorption functional layer. SUMMARY

[0007] In view of the deficiencies of the prior art, the purpose of the present application is to provide a resin, a photosensitive resin composition and applications thereof.

[0008] To achieve the above purpose, the present application adopts the following technical solutions:

[0009] In one aspect, the present application provides a resin having the following structure shown in Formula I:

[0010]

[0011] wherein R1 represents a substance containing a hindered amine structure; R2 is selected from an alkyl group of 1-5 carbon atoms; a1, a1, a2, b1 and b2 are independently integers from 1 to 30 (for example, 1, 3, 5, 8, 10, 12, 15, 18, 20, 23, 25, 28 or 30), and c is an integer from 5 to 50 (for example, 5, 8, 10, 12, 15, 18, 20, 23, 25, 28, 30, 35, 38, 40, 42, 45, 48 or 50).

[0012] The ultraviolet spectrum of chalcone compounds consists of two basic absorption bands, band I of chalcone usually appears at 220-270 nm, and band II appears at 340-390 nm. These absorption bands are generated from n→π* and π→π* electron transitions, which shows that compounds containing chalcone structure have potential application as ultraviolet absorbers. Hindered amine light stabilizers (HALS) are widely used because they do not stain, have very high light stabilizing effect and can improve heat resistance. In particular, HALS with N-OR structure can also continue to react with the peroxide radicals generated by light aging in the polymer system, consume the peroxide radicals, and at the same time regenerate active nitrogen oxide radicals and hindered amine structures, forming a benign cycle of HALS. HALS containing N-H structure is easily oxidized to a relatively stable nitrogen oxide radical structure by active species in the system, and then the nitrogen oxide radical captures the free radicals generated in the light aging process, blocking further harmful reactions in the system. By synthesis method, the present application introduces chalcone and hindered amine groups into acrylic resin, and through the absorption of chalcone structure to external ultraviolet light and the capture of free radicals generated in the light aging process by HALS structure, the acrylic resin is endowed with strong weather resistance, and the functionalized resin is applied to a photosensitive resin composition for preparing an optical film, so that the optical film has good performance.

[0013] Preferably, R1is preferably selected from hindered amine compounds containing N-OR structure, wherein R is C2-C7linear or branched hydroxylated alkyl group, and hindered amine groups containing 4-hydroxylated alkyl-2,2,6,6-tetramethylpiperidine structure.

[0014] Further preferably, R1is selected from wherein the wavy line represents the point of attachment of the group.

[0015] Preferably, R2is selected from methyl, ethyl, n-propyl, i-propyl or n-butyl.

[0016] In another aspect, the present application provides a method for preparing the resin as described above, the method comprising the steps of:

[0017] (1) a polymer of Formula III is obtained by polymerization of methyl methacrylate, acrylic acid and a chalcone compound of Formula II, as shown in the following reaction scheme:

[0018]

[0019] (2) a polymer of Formula I is obtained by reacting the polymer of Formula III with glycidyl methacrylate, as shown in the following reaction scheme:

[0020]

[0021] wherein a = a1+ a2, b = b1+ b2, a, b and c each independently represent an integer of 5-50 (e.g. 5, 8, 10, 12, 15, 18, 20, 23, 25, 28, 30, 35, 38, 40, 42, 45, 48 or 50), and a:b = 1:1-1:3 (e.g. 1:1, 1:1.3, 1:1.5, 1:2, 1:2.2, 1:2.5, 1:2.8 or 1:3); a:c = 1:1-1:5 (e.g. 1:1, 1:1.2, 1:1.5, 1:1.8, 1:2, 1:2.5, 1:2.8, 1:3, 1:3.5, 1:4, 1:4.5 or 1:5), a1, a2, b1and b2are independently an integer of 1-30 (e.g. 1, 3, 5, 8, 10, 12, 15, 18, 20, 23, 25, 28 or 30);

[0022] (3) a resin of Formula I is obtained by reacting the polymer of Formula IV with a hindered amine light stabilizer of R1-OH, as shown in the following reaction scheme:

[0023]

[0024] Preferably, the molar ratio of methacrylic acid to acrylic acid in step (1) is 1 : 1 to 1 : 3, for example 1 : 1, 1 : 1.3, 1 : 1.5, 1 : 1.8, 1 : 2, 1 : 2.3, 1 : 2.5, 1 : 2.8, or 1 : 3.

[0025] The molar ratio of methacrylic acid to chalcone compound of Formula II in step (1) is 1 : 1 to 1 : 5, for example 1 : 1, 1 : 1.3, 1 : 1.5, 1 : 1.8, 1 : 2, 1 : 2.3, 1 : 2.5, 1 : 2.8, 1 : 3, 1 : 3.5, 1 : 3.8, 1 : 4, 1 : 4.5, 1 : 4.8, or 1 : 5.

[0026] Preferably, the polymerization reaction in step (1) is carried out in the presence of a chain transfer agent.

[0027] Preferably, the chain transfer agent is selected from aliphatic mercaptans, preferably n-dodecanethiol.

[0028] Preferably, the molar ratio of the chain transfer agent to the total amount of methacrylic acid, acrylic acid, and chalcone compound of Formula II is 1 : 100 to 5 : 100, for example 1 : 100, 1.5 : 100, 2 : 100, 2.5 : 100, 3 : 100, 3.5 : 100, 4 : 100, 4.5 : 100, or 5 : 100.

[0029] Preferably, the polymerization reaction in step (1) is carried out under initiation of an initiator.

[0030] Preferably, the initiator is selected from one or a combination of at least two of azobisisobutyronitrile (AIBN), diacyl peroxide, or persulfate.

[0031] Preferably, the amount of initiator is 2% to 8% by weight of the chalcone compound of Formula II, for example 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, 5%, 5.5%, 6%, 6.5%, 7%, 7.5%, or 8%.

[0032] Preferably, the polymerization reaction in step (1) is carried out in an organic solvent.

[0033] Preferably, the organic solvent is selected from propylene glycol methyl ether acetate (PMA).

[0034] Preferably, the polymerization reaction in step (1) is carried out at 70-90°C (e.g. 70°C, 75°C, 78°C, 80°C, 85°C, 88°C or 90°C) for 1-3h (e.g. 1h, 1.5h, 2h, 2.5h or 3h), then gradually increased to a temperature of 100-110°C (e.g. 100°C, 105°C, 108°C or 110) for 1-3h (e.g. 1h, 1.5h, 2h, 2.5h or 3h), and then increased to 120-140°C (e.g. 120°C, 125°C, 128°C, 130°C, 135°C, 138°C or 140°C) for 0.5-1.5h (e.g. 0.5h, 0.8h, 1h, 1.3h or 1.5h) to remove the initiator.

[0035] In the present application, part of the solvent is added to the reaction device in the form of a bottom liquid, and then a solution of methyl methacrylate, acrylic acid, a chalcone compound represented by formula II and a chain transfer agent dissolved in a solvent and a solution of an initiator dissolved in a solvent are simultaneously dropped into the reaction device, and the dropping time is 2-2.5 times the half-life of the initiator.

[0036] In the present application, the chalcone compound represented by formula II can be prepared according to patent CN 115894939 A, which specifically includes the following steps:

[0037] Preparation of intermediate product I: anhydrous acetone, hydroxybenzaldehyde substitute and anhydrous potassium carbonate are mixed, heated and stirred to reflux, 3-bromopropene is added dropwise after reflux begins, heating and stirring are continued, the reaction is completed after cooling, and the filtrate is rotary evaporated to remove the solvent to obtain the intermediate product I, and the reaction formula is as follows:

[0038]

[0039] Chalcone preparation: intermediate product I is mixed with methoxy-substituted acetophenone and stirred to achieve complete dissolution and mixing, sodium hydroxide is added, and the target chalcone product is separated using filter paper after the reaction is completed, and the reaction formula is as follows:

[0040]

[0041] Preferably, the molar ratio of the polymer represented by formula III to glycidyl methacrylate in step (2) is 1:20-1:40, e.g. 1:20, 1:25, 1:28, 1:30, 1:33, 1:35, 1:38 or 1:40.

[0042] Preferably, the reaction in step (2) is carried out under the catalysis of a catalyst;

[0043] Preferably, the catalyst is selected from one or a combination of tetrabutylammonium bromide, tetraethylammonium bromide, triphenylphosphine, benzyltriethylammonium chloride or DBU.

[0044] Preferably, the catalyst is 0.2-1 %, for example 0.2 %, 0.4 %, 0.6 %, 0.8 % or 1 % of the sum of the moles of hydroxyl groups in the polymer of Formula III and the moles of epoxy groups in the glycidyl methacrylate.

[0045] Preferably, the reaction of step (2) is carried out in the presence of a polymerization inhibitor.

[0046] Preferably, the polymerization inhibitor is selected from a phenolic polymerization inhibitor,

[0047] Preferably, the polymerization inhibitor is selected from one or a combination of p-methoxyphenol (MEHQ), p-hydroxyanisole, 2,6-di-tert-butyl-p-cresol, 2,5-di-tert-butyl-hydroquinone or 2-tert-butyl-hydroquinone.

[0048] Preferably, the reaction of step (2) is carried out in the presence of an antioxidant.

[0049] Preferably, the antioxidant is selected from a phenolic antioxidant or a hindered phenolic antioxidant.

[0050] Preferably, the antioxidant is selected from one or a combination of BHT, ADK STAB AO-30, ADK STAB AO-40, ADK STAB AO-50 or ADK STAB AO-60.

[0051] Preferably, the reaction of step (2) is carried out at a temperature of 100 °C for 5-12 h, for example 5 h, 6 h, 7 h, 8 h, 9 h, 10 h, 11 h or 12 h.

[0052] Preferably, the molar ratio of the polymer of Formula IV to the hindered amine light stabilizer of the formula R1-OH in step (3) is 1 :20-1 :40, for example 1 :20, 1 :22, 1 :25, 1 :28, 1 :30, 1 :33, 1 :35, 1 :38, 1 :40.

[0053] Preferably, the reaction of step (3) is carried out in the presence of a catalyst.

[0054] Preferably, the catalyst is selected from any one or a combination of sulfuric acid, aluminum hydroxide, potassium hydroxide or sodium hydroxide.

[0055] Preferably, the reaction temperature in step (3) is 120-150℃, for example 120℃, 125℃, 130℃, 135℃, 140℃, 143℃, 145℃ or 150℃, and the reaction time is 2-7h, for example 2h, 3h, 4h, 5h, 6h, 7h or 8h.

[0056] On the other hand, the present invention provides a photosensitive resin composition comprising a matrix resin, a colorant, a polymerizable monomer, and an initiator, wherein the matrix resin comprises the resin described above.

[0057] Preferably, the photosensitive resin composition comprises the following components in parts by weight: 100-200 parts (e.g., 100, 120, 150, 180, or 200 parts) of matrix resin, 30-60 parts (e.g., 30, 35, 38, 40, 45, 50, 55, or 60 parts) of colorant, 50-80 parts (e.g., 50, 55, 60, 65, 70, 75, or 80 parts) of polymerizable monomer, and 3-10 parts (e.g., 3, 5, 8, or 10 parts) of initiator.

[0058] Preferably, the colorant includes any one or a combination of at least two of infrared absorbing dyes, red light absorbing dyes, green light absorbing dyes, or blue light absorbing dyes.

[0059] Preferably, the colorant includes any one or a combination of at least two of FDN-002, FDN-005, FDR-002, FDG-007, FDB-006 or FDB-007 manufactured by Yamada.

[0060] Preferably, the polymerizable monomer includes a monomer containing a carbon-carbon double bond.

[0061] Preferably, the polymerizable monomer is selected from any one or a combination of at least two of the following: tricyclodecanediethanol diacrylate, pentaerythritol triacrylate, trimethylolpropane triacrylate, pentaerythritol tetraacrylate, and dipentaerythritol hexaacrylate.

[0062] Preferably, the initiator is selected from any one or a combination of at least two of the following: oxime esters, arylalkyl ketones, benzophenones, or heterocyclic ketones.

[0063] Preferably, the oxime ester compound includes any one or a combination of at least two of OXE01, OXE02, OXE03, OXE04, OXE05, NCI-831, N-1919, NCI-930, SPI-02, SPI-03, PBG305, PBG304, PBG345, PBG314, PBG3057, and PBG3142.

[0064] Preferably, the arylalkyl ketone photoinitiator includes any one or a combination of at least two of Irgacure 184, Irgacure 819, Irgacure 907, Irgacure 369, Irgacure 1173, Irgacure 2959, and Irgacure TPO.

[0065] Preferably, the benzophenone or heterocyclic aromatic ketone includes any one or a combination of at least two of Irgacure ITX, Irgacure DETX, Irgacure BP, and Irgacure EMK.

[0066] Preferably, the photosensitive resin composition further includes other auxiliary agents.

[0067] Preferably, the other auxiliary agents include any one or a combination of at least two of a leveling agent, a filler, a sensitizer, an adhesion promoter, an antioxidant, a light stabilizer, a chain transfer agent, and a photobase generator.

[0068] Preferably, the photosensitive resin composition further includes a solvent.

[0069] Preferably, the solvent is selected from propylene glycol methyl ether (PM) and / or propylene glycol methyl ether acetate (PMA).

[0070] In another aspect, the present application provides an optical film prepared from the photosensitive resin composition as described above.

[0071] The resin of the present application is simple to prepare, and the optical film of the present application does not need to additionally prepare an ultraviolet absorption functional layer to achieve the purposes of high brightness efficiency, anti-reflection, and good reliability.

[0072] The photosensitive resin composition of the present application does not need to add black organic pigments, and there is no risk of quality degradation, and the optical film prepared therefrom has good heat resistance, high temperature and humidity resistance, light resistance, and other advantages.

[0073] Compared with the prior art, the present application has the following beneficial effects:

[0074] The resin structure of the present application is connected with a chalcone structure capable of playing the role of an ultraviolet absorber, and is also connected with a hindered amine structure capable of playing the role of light stability, and the resin has a double bond and a carboxyl group, capable of polymerization and development, and is applied to a photosensitive resin composition, and can be used to prepare an optical film capable of playing the role of anti-reflection, and the film layer has excellent reliability performance (light resistance, heat resistance, chemical resistance, high temperature and humidity resistance, etc.). DETAILED DESCRIPTION

[0075] The technical solutions of the present application are further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments are only used to help understand the present application and should not be regarded as specific limitations of the present application.

[0076] Preparation Example 1

[0077] (1) Preparation of chalcone compound (reference to CN 115894939 A, Example 1 preparation)

[0078] Preparation of intermediate product A: add 50 ml of anhydrous acetone, 12.2 g (0.1 mol) of p-hydroxybenzaldehyde and 13.8 g (0.1 mol) of anhydrous potassium carbonate into a three-necked flask, heat and stir in an oil bath at 200 rpm in a constant temperature magnetic stirrer to reflux to 56°C, then add 12.5 g (a little more than 0.1 mol) of 3-bromopropene dropwise, dropwise for about 45 min, keep refluxing for 8 h after temperature is kept, stop heating, cool to room temperature. Use 10-15 μm filter paper to filter to remove anhydrous potassium carbonate. Remove unreacted 3-bromopropene and solvent by rotary evaporation at 45°C to obtain intermediate product A.

[0079] Preparation of chalcone: weigh equal molar amounts of product A and p-methoxyphenylacetone in a single-necked flask, add 3 times the total mass of the reactants of anhydrous ethanol and stir at 150 rpm at room temperature until product I and p-methoxyphenylacetone are dissolved. Add 3M sodium hydroxide solution with anhydrous ethanol to the same volume, dropwise for about 30 min, stop the reaction after 6.5 h, filter the reaction system with 10-15 μm filter paper to separate the solid and liquid, then wash the product with petroleum ether several times, then recrystallize in 95% ethanol to obtain the methoxylated chalcone derivative, i.e. the target chalcone compound shown in formula II;

[0080]

[0081] (2) Synthesis of resin precursor (double bond polymerization reaction)

[0082] Into a four-necked flask equipped with a reflux condenser, a thermometer, and a nitrogen inlet and outlet, 75.00 g of PMA was added as a bottom liquid. The temperature was raised to the set reaction temperature of 80°C. 7.75 g of methacrylic acid, 10.05 g of acrylic acid, 61.60 g of a compound shown in Formula II, and 3.63 g of n-dodecanethiol and 2.50 g of PMA solvent as chain transfer agents were added into flask 2, respectively. 0.75 g of AIBN as an initiator was dissolved in 105.00 g of PMA and added into flask 3. After the temperature of the bottom liquid PMA was stabilized, the solutions in flasks 2 and 3 were simultaneously added dropwise into the four-necked flask, and the dropwise time was controlled to be about twice the half-life of the initiator. After the dropwise addition was completed, the reaction was continued at the same temperature for 3 h, and then gradually increased to the maximum temperature of 120°C for 1.5 h to remove the residual initiator. (The raw materials required for the reaction can be purchased through the market.)

[0083]

[0084] After the reaction was completed, the reaction product was subjected to GPC test, and the Mw was 5900, the Mn was 3200, and the PD was 1.83, proving the generation of the resin precursor substance.

[0085] (3) Introduction of hydroxyl and double bond into the resin

[0086] Resin side group carboxyl group-epoxy group reaction: glycidyl methacrylate 19.83 g was added into the above resin solution, and a polymerization inhibitor MEHQ 0.09 g and an antioxidant BHT 0.16 g were added, and the reaction was catalyzed by a catalyst at 100°C for 10 h to obtain a product B1 shown in Formula IV.

[0087]

[0088] At different time periods, the product was sampled and subjected to GPC and acid value tests, and the reaction degree was controlled by monitoring the related values. The final product had an Mw of 7900, an Mn of 4100, a PD of 1.93, and an acid value of 63.85 mg KOH / g.

[0089] (4) Introduction of hindered amine structure (2 hydroxyl groups are reacted to form an ether)

[0090] The hindered amine light stabilizer 430 was mixed with the resin shown in Formula IV obtained in the above step (3), and heated to 140°C in the presence of a catalyst 0.05 g of sulfuric acid for 3 h to obtain a target product B2 shown in Formula I.

[0091]

[0092] The product GPC and acid value were sampled and detected at different time periods to control the reaction degree by monitoring the relevant values. The final product had a Mw of 18300, a Mn of 8400, a PD of 2.18, and an acid value of 43.43 mg KOH / g.

[0093] Preparation Example 2

[0094] In the preparation of chalcone in step (1) of Preparation Example 1, the p-methoxyphenylacetone was replaced by 4-n-butoxyphenylacetone, and other processes were the same as those in Preparation Example 1. The following target product B3 was obtained. The product GPC and acid value were sampled and detected at different time periods to control the reaction degree by monitoring the relevant values. The final product had a Mw of 19500, a PD of 2.32, and an acid value of 41.05 mg KOH / g.

[0095]

[0096] Preparation Example 3

[0097] In step (4) of Preparation Example 1, the hindered amine light stabilizer 430 was replaced by the following compound R3 (prepared by the method disclosed in patent CN115819327A), and other processes were the same as those in Preparation Example 1. The following target product B4 was obtained. The product GPC and acid value were sampled and detected at different time periods to control the reaction degree by monitoring the relevant values.

[0098] The final product had a Mw of 17600, a PD of 2.10, and an acid value of 45.80 mg KOH / g.

[0099]

[0100]

[0101] The resins prepared in Preparation Examples 1-3 were used in a photosensitive resin composition, and the composition and the amount of each component are shown in Table 1.

[0102] Table 1

[0103]

[0104] Table 2

[0105]

[0106] The photosensitive resin composition of the example was prepared into an optical film of about 10 um through processes such as spin coating, pre-baking, exposure, development, post-baking, etc.

[0107] The prepared optical film layer was subjected to reliability evaluation such as heat resistance, light resistance, chemical resistance, high temperature and high humidity resistance, and the evaluation results are shown in Table 3 and Table 4.

[0108] Heat resistance: the prepared optical film is placed in a 240℃ environment, baked for 1h, then after standing at room temperature for 10min, the ultraviolet-visible light absorption of the sample before and after baking is tested respectively, and the color difference and transmittance change of the film layer before and after baking are calculated, ΔEab≤3 and ΔY≤5% are excellent, ΔEab≤10 and ΔY≤10% are good, ΔEab>10 and ΔY>10% are poor.

[0109] Light resistance: the prepared optical film is placed in a xenon lamp environment with an illumination of 6000mJ / cm 2 , a wavelength range of 300-400nm, a temperature of 60℃, and irradiation for 200h, the ultraviolet-visible light absorption of the sample before and after irradiation is tested respectively, and the color difference and transmittance change of the film layer before and after baking are calculated, ΔEab≤3 and ΔY≤5% are excellent, ΔEab≤10 and ΔY≤10% are good, ΔEab>10 and ΔY>10% are poor.

[0110] Chemical resistance: the prepared optical film is placed in PMA solvent, soaked at room temperature for 30min, the ultraviolet-visible light absorption of the optical film layer before and after soaking is tested, and the color difference and transmittance change of the film layer before and after baking are calculated, ΔEab≤3 and ΔY≤5% are excellent, ΔEab≤10 and ΔY≤10% are good, ΔEab>10 and ΔY>10% are poor.

[0111] High temperature and high humidity resistance: the prepared optical film is placed in a high temperature and high humidity device (85℃, 85% humidity), after 480h, it is placed in a room temperature environment for 2h, the ultraviolet-visible light absorption of the sample before and after treatment is tested respectively, and the color difference and transmittance change of the film layer before and after baking are calculated, ΔEab≤3 and ΔY≤5% are excellent, ΔEab≤10 and ΔY≤10% are good, ΔEab>10 and ΔY>10% are poor.

[0112] Table 3

[0113] Raw material Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Heat resistance ◎ ◎ ◎ ◎ ◎ ◎ PMA resistance ◎ ◎ ◎ ◎ ◎ ◎ Light resistance ◎ ◎ ◎ O O ◎ High temperature and high humidity O O ◎ O O ◎

[0114] Table 4

[0115] Raw material Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 Comparative Example 6 Heat resistance O O O O O O PMA resistance × × × O O × Light resistance × × × × × × High temperature and high humidity × × × × × ×

[0116] Wherein excellent:◎, good:O, poor:×.

[0117] It can be seen that the optical film prepared by using the resin of the present application has good heat resistance, light resistance, high temperature and high humidity resistance.

[0118] The applicant states that the resin, the photosensitive resin composition and the application thereof of the present application are illustrated by the above-mentioned examples, but the present application is not limited to the above-mentioned examples, i.e. it does not mean that the present application must rely on the above-mentioned examples to be implemented. The person skilled in the art should understand that any improvement of the present application, equivalent replacement of each raw material of the product of the present application, addition of auxiliary ingredients, selection of specific modes, etc. fall within the protection scope and the disclosure scope of the present application.

Claims

1. A resin characterized by, The resin has the following general structural formula as shown in Formula I: Formula I; wherein R1is selected from or wherein the wavy line represents the point of attachment of the group; R2is selected from alkyl of 1-5 carbon atoms; a1, a2, b1, and b2 are independent integers from 1 to 30, and c is an integer from 5 to 50.

2. The resin according to claim 1, characterized in that, R2 is selected from methyl, ethyl, n-propyl, isopropyl, or n-butyl.

3. The resin according to claim 1, characterized by The weight-average molecular weight of the resin is 5000-20000.

4. The process for the preparation of the resin according to any one of claims 1-3, characterized in that, The preparation method includes the following steps: (1) Under the initiation of an initiator, methacrylic acid, acrylic acid and the chalcone compound shown in Formula II undergo a polymerization reaction to obtain the polymer shown in Formula III, and the reaction formula is as follows: ； (2) The polymer shown in Formula III reacts with glycidyl methacrylate to obtain the polymer shown in Formula IV. The reaction formula is as follows: ； Where a = a1 + a2, b = b1 + b2, a, b and c are each independently represented as integers from 5 to 50, and a:b = 1:1 to 1:3; a:c = 1:1 to 1:5, a1, a2, b1 and b2 are each independently represented as integers from 1 to 30; (3) The polymer shown in Formula IV reacts with the hindered amine light stabilizer shown in R1-OH to obtain the resin shown in Formula I. The reaction formula is as follows: 。 5. The method of claim 4, wherein the resin is prepared by the steps of: The molar ratio of methacrylic acid to acrylic acid in step (1) is 1:1 to 1:

3.

6. The method of claim 4, wherein the resin is prepared by the steps of: The molar ratio of methacrylic acid to the chalcone compound shown in Formula II in step (1) is 1:1 to 1:

5.

7. The method of claim 4, wherein the resin is prepared by the steps of: The initiator is selected from azobisisobutyronitrile and / or persulfate.

8. The method of claim 4, wherein the resin is prepared by the steps of: The amount of initiator used is 2%-8% of the total weight of the monomers shown in Formula II.

9. The method of claim 4, wherein the resin is prepared by the steps of: The polymerization reaction in step (1) is carried out in an organic solvent.

10. The method of claim 9, wherein the resin is prepared by the steps of: The organic solvent is selected from propylene glycol methyl ether acetate.

11. The method of claim 4, wherein the resin is prepared by the steps of: The polymerization reaction in step (1) is first carried out at 70℃~90℃ for 1-3 hours, then gradually increased to 100℃~110℃ for 1-3 hours, and then increased to 120℃-140℃ for 0.5-1.5 hours.

12. The method of claim 4, wherein the resin is prepared by the steps of: The polymerization reaction in step (1) is carried out in the presence of a chain transfer agent.

13. The method of claim 12, wherein the resin is prepared by the process of claim 1 1. The chain transfer agent is selected from aliphatic thiols.

14. The method of claim 12, wherein the resin is prepared by the process comprising: The chain transfer agent is selected from n-dodecyl mercaptan.

15. The method of claim 12, wherein the resin is prepared by the process comprising: The molar ratio of the chain transfer agent to the total amount of methacrylic acid, acrylic acid, and the chalcone compound shown in Formula II is 1:100 to 5:

100.

16. The method of claim 4, wherein the resin is prepared by the steps of: In step (2), the molar ratio of the polymer shown in Formula III to glycidyl methacrylate is 1:20-1:

40.

17. The method of claim 4, wherein the resin is prepared by the process comprising: The reaction described in step (2) is carried out under the catalysis of a catalyst.

18. The method of claim 17, wherein the resin is prepared by the process of claim 16. The catalyst is selected from one or a combination of at least two of tetrabutylammonium bromide, tetraethylammonium bromide, triphenylphosphine, benzyltriethylammonium chloride, or DBU.

19. The method of claim 17, wherein the resin is prepared by the process of claim 16. The catalyst is 0.2%-1% of the sum of the molar numbers of hydroxyl groups in the polymer shown in Formula III and epoxy groups in glycidyl methacrylate.

20. The method of claim 12, wherein the resin is prepared by the process comprising: The reaction described in step (2) is carried out in the presence of a polymerization inhibitor.

21. The method of claim 20, wherein the resin is prepared by the process of claim 19. The polymerization inhibitor is selected from phenolic polymerization inhibitors.

22. The method of claim 21, wherein the resin is prepared by the process of claim 20. The polymerization inhibitor is selected from one or a combination of at least two of p-methoxyphenol, p-hydroxyanisole, 2,6-di-tert-butyl-p-cresol, 2,5-di-tert-butylhydroquinone, or 2-tert-butylhydroquinone.

23. The method of claim 4, wherein the resin is prepared by the process comprising: The reaction described in step (2) is carried out in the presence of an antioxidant.

24. The method of claim 23, wherein the resin is prepared by the process of claim 22. The antioxidant is selected from phenolic antioxidants.

25. The method of claim 24, wherein the resin is prepared by the process of claim 23. The antioxidant is selected from one or a combination of at least two of BHT, ADK STAB AO-30, ADK STAB AO-40, ADK STAB AO-50, or ADK STAB AO-60.

26. The method of claim 4, wherein the resin is prepared by the process comprising: The temperature of the reaction in step (2) is 100°C for 5-12h.

27. The method of claim 4, wherein the resin is prepared by the process comprising: The molar ratio of the polymer of Formula IV to the hindered amine light stabilizer of R1-OH in step (3) is 1:20-1:

40.

28. The method of claim 4, wherein the resin is prepared by the process comprising: The reaction in step (3) is catalyzed by a catalyst.

29. The method of claim 28, wherein the resin is prepared by the process of claim 27. The catalyst is selected from any one or a combination of at least two of sulfuric acid, aluminum hydroxide, potassium hydroxide, or sodium hydroxide.

30. The method of claim 4, wherein the resin is prepared by the process comprising: The temperature of the reaction in step (3) is 120-150°C for 2-7h.

31. A photosensitive resin composition, characterized by comprising: The photosensitive resin composition comprises a base resin, a color material, a polymerizable monomer, and an initiator, wherein the base resin comprises the resin of any one of claims 1-3.

32. The photosensitive resin composition according to claim 31, characterized by The photosensitive resin composition comprises the following components by weight: 100-200 parts of a base resin, 30-60 parts of a color material, 50-80 parts of a polymerizable monomer, and 3-10 parts of an initiator.

33. The photosensitive resin composition according to claim 32, wherein The color material comprises any one or a combination of at least two of an infrared absorbing dye, a red light absorbing dye, a green light absorbing dye, or a blue light absorbing dye.

34. The photosensitive resin composition according to claim 33, wherein The color material comprises any one or a combination of at least two of FDN-002, FDN-005, FDR-002, FDG-007, FDB-006, or FDB-007.

35. The photosensitive resin composition according to claim 32, wherein The polymerizable monomer comprises a monomer containing a carbon-carbon double bond.

36. The photosensitive resin composition according to claim 35, wherein The polymerizable monomer is selected from any one or a combination of at least two of tricyclodecane dimethanol diacrylate, pentaerythritol triacrylate, trimethylolpropane triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate.

37. The photosensitive resin composition according to claim 32, wherein The initiator is selected from any one or a combination of at least two of an oxime ester compound, an arylalkyl ketone initiator, a benzophenone, or a heterocyclic aromatic ketone compound.

38. The photosensitive resin composition according to claim 37, wherein The oxime ester compound comprises any one or a combination of at least two of OXE01, OXE02, OXE03, OXE04, OXE05, NCI-831, N-1919, NCI-930, SPI-02, SPI-03, PBG305, PBG304, PBG345, PBG314, PBG3057, PBG3142.

39. The photosensitive resin composition according to claim 37, wherein The arylalkyl ketone initiator comprises any one or a combination of at least two of photoinitiator 184, photoinitiator 819, photoinitiator 907, photoinitiator 369, photoinitiator 1173, photoinitiator 2959, photoinitiator TPO.

40. The photosensitive resin composition according to claim 37, wherein The benzophenone or heterocyclic aromatic ketone comprises any one or a combination of at least two of photoinitiator ITX, photoinitiator DETX, photoinitiator BP, photoinitiator EMK.

41. The photosensitive resin composition according to claim 31, wherein The photosensitive resin composition further comprises other auxiliary agents.

42. The photosensitive resin composition according to claim 41, wherein The other auxiliary agents comprise any one or a combination of at least two of a leveling agent, a filler, a sensitizer, an adhesion promoter, an antioxidant, a light stabilizer, a chain transfer agent, a photobase generator.

43. The photosensitive resin composition according to claim 31, wherein The photosensitive resin composition further includes a solvent.

44. The photosensitive resin composition according to claim 43, wherein The solvent is selected from propylene glycol methyl ether and / or propylene glycol methyl ether acetate.

45. An optical film characterized by, The optical film is prepared from the photosensitive resin composition of any one of claims 31-44.

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