Boron-containing organosilicon, optical adhesive, organosilicon OCA, and preparation method and application thereof

Abstract

The present invention provides a kind of boron-containing organosilicon, optical adhesive, organosilicon OCA and preparation method and application thereof, the preparation raw materials of the boron-containing organosilicon include a combination of silanol, siloxane monomer and boric acid compound;In the preparation raw materials of the boron-containing organosilicon, the ratio of the total molar amount of hydroxyl group to the total molar amount of alkoxy group is (0.8-1.1):1, and the ratio of the total molar amount of B element to the total molar amount of Si element is 1:(5-11.5).The boron-containing organosilicon provided by the present invention makes the compatibility of the organosilicon material in the boron-containing organosilicon and the optical adhesive good by the design of preparation raw materials, is excellent in the tackifying effect of the optical adhesive, and is made to have excellent low temperature resistance and high temperature and high humidity resistance.

Description

Technical Field

[0001] The present invention belongs to the technical field of organosilicon packaging materials, and specifically relates to a boron-containing organosilicon, an optical adhesive, an organosilicon OCA, and a preparation method and application thereof. Background Art

[0002] OCA optical adhesive is a double-sided laminating tape made of a base material without a release film attached to the upper and lower layers of the adhesive layer. It is a type of pressure-sensitive adhesive and is widely used in the field of optical displays. For example, it is used for bonding display modules, glass cover plates, touch screens and other display units. It has the characteristics of high light transmittance and high bonding strength. Currently, OCA optical adhesives can be divided into acrylate OCA, silicone OCA, polyurethane OCA, epoxy resin OCA, etc. according to the type of material used. Compared with the other types of OCA, silicone OCA has better weather resistance, yellowing resistance, aging resistance, and easy rework. However, silicone OCA currently generally has poor initial adhesion, and its peel strength is much lower than that of other resins. If the initial adhesion is too low, it cannot be transferred immediately after bonding, resulting in low production efficiency. In addition, the bonding components are prone to falling off during the transfer of the display, causing losses.

[0003] At present, adding tackifiers to silicone materials is a common method to solve the problem of adhesion between materials and substrates. However, in the actual production process, conventional tackifiers have poor compatibility with silicone materials and have no obvious tackifying effect on the substrate. Under certain temperature and humidity, the bonding force decreases significantly, resulting in serious separation between the silicone resin material and the substrate.

[0004] CN102775611A discloses a tackifier and a production method thereof. The light yellow liquid organosilicon tackifier is obtained by reacting hydroxy silicone oil, γ-glycidoxypropyltrimethoxysilane, and γ-methylpropionyloxypropyltrimethoxysilane under the catalytic action of organotin. However, the organotin catalyst in the tackifier is difficult to completely remove, which seriously affects the normal curing of addition-type liquid silicone rubber.

[0005] CN104774333A discloses a thickener for addition-type silicone rubber produced by the catalytic reaction of vinyl hydroxy silicone oil, glycidyl ether alkoxysilane, and titanate. However, titanate, especially titanate complexes, are generally yellow or even dark brown. The prepared thickener is colored, which may have an adverse effect on the preparation of colorless or light-colored addition-type organic silicone adhesives.

[0006] CN109824899A discloses an addition-type thickener for silica gel, which is prepared by reacting epoxydialkoxysilane, boric acid, and vinyldialkoxysilane under the catalysis of an alkaline anion exchange resin. However, the ion exchange resin may break during the reaction, and there is a risk of incomplete filtration during the subsequent decompression and filtration to remove the catalyst.

[0007] Therefore, there is an urgent need to design a tackifier that has good compatibility with silicone materials, excellent viscosity-increasing effect, and can improve the low-temperature resistance and high-temperature and high-humidity resistance of silicone OCA. Summary of the Invention

[0008] In view of the shortcomings of the existing technology, the purpose of the present invention is to provide a boron-containing organosilicon, an optical adhesive, an organosilicon OCA and its preparation method and application. Through the design of the preparation raw materials, the boron-containing organosilicon has good compatibility with the organosilicon material in the optical adhesive, has an excellent viscosity-enhancing effect on the optical adhesive, and has excellent low-temperature resistance and high-temperature and high-humidity resistance.

[0009] To achieve this object, the present invention adopts the following technical solutions:

[0010] In a first aspect, the present invention provides a boron-containing organosilicon, wherein the raw materials for preparing the boron-containing organosilicon include a combination of silanol, a siloxane monomer and a boric acid compound; in the raw materials for preparing the boron-containing organosilicon, the ratio of the total molar amount of hydroxyl groups to the total molar amount of alkoxy groups is (0.8-1.1):1, and the ratio of the total molar amount of element B to the total molar amount of element Si is 1:(5-11.5).

[0011] The present invention forms a boron-containing organosilicon polymer macromolecule, i.e., boron-containing organosilicon, through siloxane monomers, silanols, and boric acid compounds. The target product structure is more controllable and free of by-products. Since the B atom has an electron vacancy, it can serve as an acceptor for unpaired electrons on the polysiloxane chain segment or on the surface of the substrate, forming an electron bridge between adjacent molecules, thereby forming a weak bond link. Furthermore, the molecular structure of the boron-containing organosilicon provided by the present invention contains a Si-OB bond, which can, to a certain extent, physically crosslink the organosilicon (OCA) with the substrate. Therefore, adding the boron-containing organosilicon provided by the present invention to an optical adhesive can ensure that the optical adhesive has good bonding properties with glass, ink, and polarizers after curing. Furthermore, the introduction of the B element can disrupt the regularity of the chain segment, thereby lowering the Tg of the boron-containing organosilicon and improving the low-temperature resistance of the organosilicon (OCA).

[0012] The boron-containing organosilicon provided by the present invention contains no catalyst in the raw materials for preparing the boron-containing organosilicon, thereby avoiding to a certain extent the adverse effects of catalyst residues on the color, curing, etc. of the optical adhesive. The present invention effectively regulates the structure of the boron-containing organosilicon by introducing silanols, controls the molar ratio of hydroxyl to alkoxy groups in the reaction system, promotes the thorough condensation reaction, improves the yield of the boron-containing organosilicon, and at the same time reduces the residual amount of alkoxy groups in the boron-containing organosilicon, thereby avoiding the hydrolysis of alkoxy groups during subsequent use and storage, which causes the boron-containing organosilicon to fog, thereby failing to meet the use requirements of the optical adhesive. In addition, compared with fatty alcohols, silanols have better compatibility with siloxane monomers and boric acid compounds, do not separate into phases after feeding, and react more thoroughly. Compared with hydroxy silicone oils, silanols have higher reaction activity and can form a tighter network structure, thereby effectively enhancing the hydrolysis resistance of the boron-containing organosilicon to a certain extent.

[0013] In the present invention, “the ratio of the total molar amount of hydroxyl groups to the total molar amount of alkoxy groups in the preparation raw materials of the boron-containing organosilicon is (0.8-1.1):1” means that the ratio of the total molar amount of hydroxyl groups to the total molar amount of alkoxy groups contained in all the preparation raw materials of the boron-containing organosilicon is (0.8-1.1):1; and “the ratio of the total molar amount of element B to the total molar amount of element Si is 1:(5-11.5)” means that the ratio of the total molar amount of element B to the total molar amount of element Si contained in all the preparation raw materials of the boron-containing organosilicon is 1:(5-11.5).

[0014] In the raw materials for preparing the boron-containing organosilicon, hydroxyl groups are derived from silanol silanols and boron hydroxyl groups of boric acid compounds, and the ratio of the total molar amount of hydroxyl groups to the total molar amount of alkoxy groups is (0.8-1.1):1, for example, it can be 0.82:1, 0.84:1, 0.86:1, 0.88:1, 0.9:1, 0.92:1, 0.94:1, 0.96:1, 0.98:1, 1:1, 1.02:1, 1.04:1, 1.06:1, 1.08:1, etc.

[0015] In the raw materials for preparing the boron-containing organosilicon, the ratio of the total molar amount of the B element to the total molar amount of the Si element is 1:(5-11.5), for example, it can be 1:5.1, 1:5.2, 1:5.5, 1:6, 1:6.5, 1:7, 1:7.5, 1:8, 1:8.5, 1:9, 1:9.5, 1:10, 1:10.5, 1:11, etc.

[0016] The present invention controls the molar ratio of the B element to the Si element in the preparation raw materials of the boron-containing organosilicon within a suitable range, thereby obtaining a boron-containing organosilicon with a good adhesion-promoting effect and no significant change in hydrolysis resistance. If the molar ratio of the B element to the Si element is too large, the bonding performance of the optical adhesive is improved but the hydrolysis resistance is deteriorated because the BO-Si bond is much more sensitive to hydrolysis than the Si-O-Si bond and is more easily broken by hydrolysis. If the molar ratio of the B element to the Si element is too small, the improvement in the adhesion performance of the organosilicon OCA is not obvious.

[0017] The following are preferred technical solutions of the present invention, but are not intended to limit the technical solutions provided by the present invention. Through the following preferred technical solutions, the objectives and beneficial effects of the present invention can be better achieved and realized.

[0018] As a preferred technical solution, the general formula of the silanol is R 11 4-a Si(OH) a ; Among them, R 11 Each is independently selected from any one of C1-C5 straight or branched alkyl groups and C3-C8 cyclic hydrocarbon groups; a is 2 or 3.

[0019] In the present invention, "each independently" means that when there are multiple subjects, they can be the same or different from each other, and the following descriptions involving the same subject have the same meaning.

[0020] Preferably, the silanol includes any one of dimethylsilanediol, methylethylsilanediol, methylphenylsilanediol, methylsilanetriol or phenylsilanetriol, or a combination of at least two thereof.

[0021] Preferably, the general formula of the siloxane monomer is R 12 4-b Si(OR 13 ) b ; Among them, R 12 Each independently selected from any one of a C2-C6 unsaturated hydrocarbon group, a C1-C5 straight chain or branched alkyl group; R 13 Each is independently selected from any one of C1-C5 straight or branched alkyl groups; b is selected from an integer of 1-3, more preferably 2 or 3.

[0022] In the present invention, the C1-C5 can each independently be C2, C3, C4, etc.

[0023] The C3-C8 can each independently be C4, C5, C6, C7, etc.

[0024] The C1-C5 straight or branched chain alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, 2-methylbutyl, n-pentyl, isopentyl, neopentyl, and the like.

[0025] The C3-C8 cycloalkyl group includes any one of a C3-C8 cycloalkyl group or a phenyl group; the C3-C8 cycloalkyl group illustratively includes but is not limited to: a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like.

[0026] The C2-C6 unsaturated hydrocarbon group includes any one of the C2-C6 alkenyl groups, illustratively including but not limited to ethenyl, propenyl, butenyl and the like.

[0027] Preferably, the siloxane monomer comprises a first siloxane monomer, a second siloxane monomer and optionally a third siloxane monomer; the general formula of the first siloxane monomer is R A1 2Si(OR A2 ) 2; the general formula of the second siloxane monomer is R B1 Si(OR B2 ) 3; the general formula of the third siloxane monomer is R C1 3SiOR C2 ; Among them, R A1 、R B1 、R C1 Each independently selected from any one of a C2-C6 unsaturated hydrocarbon group, a C1-C5 straight chain or branched alkyl group; R A2 、R B2 、R C2 Each is independently selected from any one of C1-C5 straight chain or branched chain alkyl groups.

[0028] Preferably, the first siloxane monomer includes any one of methylvinyldimethoxysilane, dimethyldimethoxysilane or dimethyldiethoxysilane, or a combination of at least two thereof.

[0029] Preferably, the second siloxane monomer includes methyltrimethoxysilane and / or methyltriethoxysilane.

[0030] Preferably, the third siloxane monomer comprises trimethylmethoxysilane.

[0031] Preferably, the boric acid compound includes any one of boric acid, phenylboric acid or tetrahydroxyboron, or a combination of at least two thereof.

[0032] Preferably, the molar ratio of the hydroxyl group in the boric acid compound to the hydroxyl group in the silanol is 1:(1-7), for example, it can be 1:1, 1:1.5, 1:2, 1:2.5, 1:3, 1:3.5, 1:4, 1:4.5, 1:5, 1:5.5, 1:6, etc.

[0033] Preferably, in the preparation raw materials of the boron-containing organosilicon, the ratio of the total molar amount of the B element to the total molar amount of the Si element is 1:(6.5-11.5) (for example, 1:6.6, 1:6.8, 1:7, 1:7.2, 1:7.4, 1:7.6, 1:7.8, 1:8.2, 1:8.6, 1:9.2, 1:9.4, 1:10.2, 1:10.6, 1:11.2, 1:11.4, etc.), and further preferably 1:(7-8.5) (for example, 1:7.1, 1:7.3, 1:7.7, 1:7.9, 1:8.1, 1:8.3, 1:8.4, etc.).

[0034] When the molar ratio of the B element to the Si element in the raw materials for preparing the boron-containing organosilicon of the present invention is 1:(7-8.5), the hydrolysis resistance of the boron-containing organosilicon can be optimized, and the bonding performance of the organosilicon OCA can be improved.

[0035] Preferably, the raw materials for preparing the boron-containing organosilicon further include a solvent.

[0036] Preferably, the solvent includes any one or a combination of at least two of N,N-dimethylformamide, dimethyl sulfoxide, methanol, acetonitrile, isopropanol, 1,4-dioxane or cyclohexanone.

[0037] Preferably, based on the total mass of the silanol, siloxane monomer and boric acid compound as 100%, the mass of the solvent is 25-40%, for example, it can be 25.5%, 26%, 26.5%, 27%, 27.5%, 28%, 28.5%, 29%, 29.5%, 30%, 30.5%, 31%, 31.5%, 32%, 32.5%, 33%, 33.5%, 34%, 34.5%, 35%, 35.5%, 36%, 36.5%, 37%, 37.5%, 38%, 39%, etc.

[0038] In a second aspect, the present invention provides a method for preparing the boron-containing organosilicon as described in the first aspect, the preparation method comprising:

[0039] The boron-containing organosilicon is obtained by reacting silanol and siloxane monomers with boric acid compounds.

[0040] The boron-containing organosilicon is prepared by the preparation method provided by the present invention with high yield and no by-products, and the yield is 72-87%.

[0041] Preferably, the reaction temperature is 80-140°C, for example, 85°C, 90°C, 95°C, 100°C, 105°C, 110°C, 115°C, 120°C, 125°C, 130°C, 135°C, etc.

[0042] Preferably, the reaction time is 3-7 h, for example, 3.2 h, 3.5 h, 3.8 h, 4 h, 4.2 h, 4.5 h, 4.8 h, 5 h, 5.2 h, 5.5 h, 5.8 h, 6 h, 6.2 h, 6.5 h, 6.8 h, etc.

[0043] Preferably, the reaction is carried out in the presence of a solvent.

[0044] Preferably, after the reaction is completed, the step of reduced pressure distillation is further included to remove the solvent in the reaction system by the reduced pressure distillation.

[0045] In a third aspect, the present invention provides a use of the boron-containing organosilicon as described in the first aspect, wherein the boron-containing organosilicon is used as a tackifier in an optical adhesive.

[0046] In a fourth aspect, the present invention provides an optical adhesive, wherein the raw materials for preparing the optical adhesive include, in parts by weight:

[0047]

[0048] The vinyl silicone resin is 10-30 parts by weight, for example, 12 parts by weight, 14 parts by weight, 16 parts by weight, 18 parts by weight, 20 parts by weight, 22 parts by weight, 24 parts by weight, 26 parts by weight, 28 parts by weight, etc.

[0049] The vinyl silicone oil is 30-50 parts by weight, for example, 32 parts by weight, 34 parts by weight, 36 parts by weight, 38 parts by weight, 40 parts by weight, 42 parts by weight, 44 parts by weight, 46 parts by weight, 48 parts by weight, etc.

[0050] The hydrogenated silicone oil is 5-20 parts by weight, for example, 6 parts by weight, 8 parts by weight, 10 parts by weight, 12 parts by weight, 14 parts by weight, 16 parts by weight, 18 parts by weight, etc.

[0051] The hydrogenated silicone resin is present in an amount of 10-30 parts by weight, for example, 12 parts by weight, 14 parts by weight, 16 parts by weight, 18 parts by weight, 20 parts by weight, 22 parts by weight, 24 parts by weight, 26 parts by weight, 28 parts by weight, etc.

[0052] The catalyst is present in an amount of 0.01-0.5 parts by weight, for example, 0.05 parts by weight, 0.1 parts by weight, 0.15 parts by weight, 0.2 parts by weight, 0.25 parts by weight, 0.3 parts by weight, 0.35 parts by weight, 0.4 parts by weight, 0.45 parts by weight, etc.

[0053] The boron-containing organosilicon is 0.1-15 parts by weight, for example, 0.5 parts by weight, 1 part by weight, 1.5 parts by weight, 2 parts by weight, 2.5 parts by weight, 3 parts by weight, 3.5 parts by weight, 4 parts by weight, 4.5 parts by weight, 5 parts by weight, 5.5 parts by weight, 6 parts by weight, 6.5 parts by weight, 7 parts by weight, 7.5 parts by weight, 8 parts by weight, 8.5 parts by weight, 9 parts by weight, 9.5 parts by weight, 10 parts by weight, 11 parts by weight, 12 parts by weight, 13 parts by weight, 14 parts by weight, etc.

[0054] Preferably, the vinyl silicone resin includes any one of vinyl MQ silicone resin, vinyl MDT silicone resin, vinyl MTQ silicone resin or vinyl DT silicone resin, or a combination of at least two thereof.

[0055] Preferably, the viscosity of the vinyl silicone resin at 25°C is 5000-50000 mPa·s, for example, it can be 5500 mPa·s, 6000 mPa·s, 6500 mPa·s, 7000 mPa·s, 7500 mPa·s, 8000 mPa·s, 8500 mPa·s, 9000 mPa·s, 9500 mPa·s, 10000 mPa·s, 15000 mPa·s, 20000 mPa·s, 25000 mPa·s, 30000 mPa·s, 35000 mPa·s, 40000 mPa·s, 45000 mPa·s, etc.

[0056] Preferably, the vinyl content of the vinyl silicone resin is 0.3-1.0 mmol / g, for example, it can be 0.35 mmol / g, 0.4 mmol / g, 0.45 mmol / g, 0.5 mmol / g, 0.55 mmol / g, 0.6 mmol / g, 0.65 mmol / g, 0.7 mmol / g, 0.75 mmol / g, 0.8 mmol / g, 0.85 mmol / g, 0.9 mmol / g, 0.95 mmol / g, etc.

[0057] Preferably, the vinyl silicone oil includes any one or a combination of at least two of silicone oil containing vinyl groups at the terminal, silicone oil containing vinyl groups at the side groups, and silicone oil containing vinyl groups at both the terminal and side groups.

[0058] Preferably, the viscosity of the vinyl silicone oil at 25° C. is 100-20,000 mPa·s, for example, 500 mPa·s, 1000 mPa·s, 1500 mPa·s, 2000 mPa·s, 2500 mPa·s, 3000 mPa·s, 3500 mPa·s, 4000 mPa·s, 4500 mPa·s, 5000 mPa·s, 5500 mPa·s, 6000 mPa·s, 6500 mPa·s, 7000 mPa·s, 7500 mPa·s, 8000 mPa·s, 8500 mPa·s, 9000 mPa·s, 9500 mPa·s, 10,000 mPa·s, 15,000 mPa·s, 20,000 mPa·s, etc.

[0059] Preferably, the vinyl content of the vinyl silicone oil is 0.1-0.75 mmol / g, for example, it can be 0.15 mmol / g, 0.2 mmol / g, 0.25 mmol / g, 0.3 mmol / g, 0.35 mmol / g, 0.4 mmol / g, 0.45 mmol / g, 0.5 mmol / g, 0.55 mmol / g, 0.6 mmol / g, 0.65 mmol / g, 0.7 mmol / g, etc.

[0060] Preferably, the general formula of the hydrogenated silicone resin is (R 21 R 22 R 23 SiO 1 / 2 ) x (R 24 R 25 SiO 2 / 2 ) y (R 26 SiO 3 / 2 ) z ; Among them, R 21 、R 22 、R 23 、R 24 、R 25 、R 26 are independently selected from any one of a hydrogen atom, a C1-C5 straight chain or branched alkyl group, and R 21 、R 22 、R 23 、R 24 、R 25 、R 26At least one of them is a hydrogen atom; x:y:z is the molar ratio of each link, and x:y:z=1:(0.2-0.3):(2-3), for example, it can be 1:0.21:2.1, 1:0.22:2.2, 1:0.23:2.3, 1:0.24:2.4, 1:0.25:2.5, 1:0.26:2.6, 1:0.27:2.7, 1:0.28:2.8, 1:0.29:2.9, etc.

[0061] Preferably, the viscosity of the hydrogenated silicone resin at 25° C. is 10,000-40,000 mPa·s, for example, 12,000 mPa·s, 14,000 mPa·s, 16,000 mPa·s, 18,000 mPa·s, 20,000 mPa·s, 22,000 mPa·s, 24,000 mPa·s, 26,000 mPa·s, 28,000 mPa·s, 30,000 mPa·s, 32,000 mPa·s, 34,000 mPa·s, 36,000 mPa·s, 38,000 mPa·s, etc.

[0062] Preferably, the silicon hydrogen content of the hydrogen-containing silicone resin is 0.1-1.2 mmol / g, for example, it can be 0.15 mmol / g, 0.2 mmol / g, 0.25 mmol / g, 0.3 mmol / g, 0.35 mmol / g, 0.4 mmol / g, 0.45 mmol / g, 0.5 mmol / g, 0.55 mmol / g, 0.6 mmol / g, 0.65 mmol / g, 0.7 mmol / g, 0.75 mmol / g, 0.8 mmol / g, 0.85 mmol / g, 0.9 mmol / g, 0.95 mmol / g, 1 mmol / g, 1.05 mmol / g, 1.1 mmol / g, 1.15 mmol / g, etc.

[0063] Preferably, the general formula of the hydrogen-containing silicone oil is (R 31 R 32 R 33 SiO 1 / 2 ) p (R 34 R 35 SiO 2 / 2 ) m (R 36 R 37 SiO 2 / 2 ) n ; Among them, R 31 、R 32 、R 33 、R 34 、R 35 、R 36 、R 37are independently selected from any one of a hydrogen atom, a C1-C5 straight chain or branched alkyl group, and R 34 、R 35 、R 36 、R 37 At least one is a hydrogen atom; 1≤p≤2, 0≤m≤50 (for example, 2, 5, 8, 10, 12, 15, 20, 25, 30, 35, 40, 45, etc.), 0≤n≤50 (for example, 2, 5, 8, 10, 12, 15, 20, 25, 30, 35, 40, 45, etc.), and m and n are not 0 at the same time.

[0064] Preferably, the viscosity of the hydrogen-containing silicone oil at 25° C. is 100-3000 mPa·s, for example, 200 mPa·s, 400 mPa·s, 500 mPa·s, 600 mPa·s, 800 mPa·s, 1000 mPa·s, 1200 mPa·s, 1500 mPa·s, 1800 mPa·s, 2000 mPa·s, 2200 mPa·s, 2500 mPa·s, 2800 mPa·s, etc.

[0065] Preferably, the silicon hydrogen content of the hydrogen-containing silicone oil is 0.05-0.5 mmol / g, for example, it can be 0.1 mmol / g, 0.15 mmol / g, 0.2 mmol / g, 0.25 mmol / g, 0.3 mmol / g, 0.35 mmol / g, 0.4 mmol / g, 0.45 mmol / g, etc.

[0066] Preferably, in the raw materials for preparing the optical adhesive, the ratio of the total molar amount of vinyl groups to the total molar amount of silyl groups is (0.95-1.05):1, for example, it can be 0.96:1, 0.97:1, 0.98:1, 0.99:1, 1:1, 1.01:1, 1.02:1, 1.03:1, 1.04:1, etc.

[0067] Preferably, the catalyst comprises any one of chloroplatinic acid, Karstedt platinum catalyst or Willing platinum catalyst, or a combination of at least two thereof.

[0068] Preferably, the raw materials for preparing the optical adhesive also include 0.2-0.5 parts by weight of an inhibitor, for example, 0.22 parts by weight, 0.24 parts by weight, 0.26 parts by weight, 0.28 parts by weight, 0.3 parts by weight, 0.32 parts by weight, 0.34 parts by weight, 0.36 parts by weight, 0.38 parts by weight, 0.4 parts by weight, 0.42 parts by weight, 0.44 parts by weight, 0.46 parts by weight, 0.48 parts by weight, etc.

[0069] Preferably, the inhibitor comprises an alcohol compound containing an unsaturated group and / or a siloxane containing at least two vinyl groups.

[0070] Preferably, the alcohol compound containing an unsaturated group includes any one of the alcohol compounds containing a carbon-carbon triple bond.

[0071] Preferably, the inhibitor includes any one of 1,4-butynediol, ethynylcyclohexanol, tetramethyltetravinylcyclotetrasiloxane or 2-methyl-3-butyn-2-ol, or a combination of at least two thereof.

[0072] In a fifth aspect, the present invention provides an organosilicon OCA, comprising a first release film, an optical adhesive layer, and a second release film stacked in sequence; the optical adhesive layer is formed by curing the optical adhesive as described in the fourth aspect.

[0073] Preferably, the thickness of the optical adhesive layer is 50-500 μm, for example, 100 μm, 150 μm, 200 μm, 250 μm, 300 μm, 350 μm, 400 μm, 450 μm, etc.

[0074] Preferably, the first release film and the second release film are each independently selected from any one of a non-silicone release film and a fluorine release film.

[0075] Preferably, the thickness of the first release film and the second release film is independently 20-2000μm, for example, it can be 60μm, 70μm, 80μm, 90μm, 100μm, 110μm, 120μm, 130μm, 140μm, 150μm, 160μm, 170μm, 180μm, 190μm, 200μm, 400μm, 600μm, 800μm, 1000μm, 1200μm, 1400μm, 1600μm, 1800μm, etc.

[0076] Preferably, the release force difference between the first release film and the second release film is 15-20gf / 25mm, for example, it can be 15.5gf / 25mm, 16gf / 25mm, 16.5gf / 25mm, 17gf / 25mm, 17.5gf / 25mm, 18gf / 25mm, 18.5gf / 25mm, 19gf / 25mm, 19.5gf / 25mm, etc.

[0077] In a sixth aspect, the present invention provides a use of the optical adhesive as described in the fourth aspect or the organosilicon OCA as described in the fifth aspect in display bonding.

[0078] Compared with the prior art, the present invention has the following beneficial effects:

[0079] (1) The boron-containing organosilicon provided by the present invention has a more controllable structure and no by-products through the design of the raw materials for preparation. It can be used as a tackifier in optical adhesives. It has good compatibility with the organosilicon material in the optical adhesive and has an excellent tackifying effect on the optical adhesive. It can make the organosilicon OCA have good initial bonding performance with glass, ink, and polarizer, and can improve the low temperature resistance and high temperature and high humidity resistance of the organosilicon OCA.

[0080] (2) Using the organosilicon OCA containing boron silicone provided by the present invention, the initial peeling force on ink is 5.358-11.323 N / 25mm, and the peeling force after 5 minutes is 15.837-22.385 N / 25mm; the initial peeling force on glass is 5.354-11.997 N / 25mm, and the peeling force after 5 minutes is 15.625-22.315 N / 25mm; the initial peeling force on polarizer is 5.035-9.591 N / 25mm, and the peeling force after 5 minutes is 16.325-22.516 N / 25mm;

[0081] (3) The light transmittance of the organosilicon OCA using the boron-containing organosilicon provided by the present invention is 91.35-92.91%, the glass transition temperature is -50 to -40°C, the initial haze is 0.11-0.18%, the haze after aging at 105°C for 1000 hours is 0.10-0.17%, and the haze after aging at 85°C / 85% RH for 1000 hours is 0.26-0.29%. BRIEF DESCRIPTION OF THE DRAWINGS

[0082] Figure 1 is an infrared spectrum of the boron-containing organosilicon provided in Example 2;

[0083] Figure 2 This is the gel permeation chromatogram of the boron-containing organosilicon provided in Example 2. DETAILED DESCRIPTION

[0084] The technical solution of the present invention will be further described below with reference to the accompanying drawings and through specific embodiments. It should be understood by those skilled in the art that the embodiments are merely to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0085] Example 1

[0086] A boron-containing organosilicon, wherein the raw materials for preparing the boron-containing organosilicon include dimethylsilanediol, methyltrimethoxysilane, dimethyldimethoxysilane, boric acid and cyclohexanone;

[0087] The preparation method of the boron-containing organosilicon comprises:

[0088] A dry round-bottom flask equipped with a mechanical stirrer, a thermometer, and a vacuum device was placed in an oil bath, and 161.30 g of dimethylsilanediol, 46.37 g of boric acid, 102.17 g of methyltrimethoxysilane, 210.38 g of dimethyldimethoxysilane, and 173 g of cyclohexanone were added to the round-bottom flask. The molar ratio of hydroxyl to alkoxy in the reaction system was 1:1, and the molar ratio of element B to element Si was 1:5.7. After the materials were uniformly stirred by mechanical stirring at room temperature, the oil bath was heated to 100°C and reacted for 4 hours. Subsequently, the oil temperature was raised to 160°C, and the solvent was removed by distillation under reduced pressure to obtain a colorless, transparent liquid product with a yield of 74%. No abnormalities were observed after being placed at room temperature for 2 months.

[0089] Example 2

[0090] A boron-containing organosilicon, wherein the raw materials for preparing the boron-containing organosilicon include dimethylsilanediol, methyltrimethoxysilane, dimethyldimethoxysilane, boric acid and cyclohexanone;

[0091] The preparation method of the boron-containing organosilicon comprises:

[0092] A dry round-bottom flask equipped with a mechanical stirrer, a thermometer, and a vacuum device is placed in an oil bath, and 161.30 g of dimethylsilanediol, 38.64 g of boric acid, 102.17 g of methyltrimethoxysilane, 210.38 g of dimethyldimethoxysilane, and 170 g of cyclohexanone are added to the round-bottom flask. The molar ratio of hydroxyl to alkoxy in the reaction system is 0.93:1, and the molar ratio of element B to element Si is 1:6.8. After the materials are uniformly stirred by mechanical stirring at room temperature, the oil bath is heated to 100° C. and reacted for 4 h. Subsequently, the oil temperature is raised to 160° C., and the solvent is distilled off under reduced pressure to obtain a colorless, transparent liquid product with a yield of 85%. No abnormality is observed after standing at room temperature for 2 months.

[0093] The boron-containing organosilicon was tested using a German Bruker Fourier infrared spectrometer (model: ALPHA). The test results are as follows: Figure 1 As shown in the infrared spectrum of boron-containing organosilicon provided in Example 2, Figure 1 It can be seen at 1340cm -1 There is an obvious Si-OB characteristic peak at

[0094] The sample was prepared with tetrahydrofuran as the mobile phase (concentration of 0.02 g / mL), injection volume of 10 μL, flow rate of 1 mL / min, and polystyrene as the standard sample. The standard curve was tested at 40°C using a Waters 2414 differential refractive index detector. The test results are shown in Figure 2. Figure 2 As shown in the gel permeation chromatogram of boron-containing organosilicon provided in Example 2, Figure 2It can be seen that the boron-containing organosilicon synthesized in Example 2 has a number average molecular weight of 18721 and a dispersion coefficient of 1.36.

[0095] Example 3

[0096] A boron-containing organosilicon, wherein the raw materials for preparing the boron-containing organosilicon include dimethylsilanediol, methyltrimethoxysilane, dimethyldimethoxysilane, boric acid and cyclohexanone;

[0097] The preparation method of the boron-containing organosilicon comprises:

[0098] A dry round-bottom flask equipped with a mechanical stirrer, a thermometer, and a vacuum device was placed in an oil bath, and 161.30 g of dimethylsilanediol, 35.55 g of boric acid, 95.35 g of methyltrimethoxysilane, 210.38 g of dimethyldimethoxysilane, and 167 g of cyclohexanone were added to the round-bottom flask. The molar ratio of hydroxyl to alkoxy in the reaction system was 0.93:1, and the molar ratio of element B to element Si was 1:7.3. After the materials were uniformly stirred by mechanical stirring at room temperature, the oil bath was heated to 100°C and reacted for 4 hours. Subsequently, the oil temperature was raised to 160°C, and the solvent was distilled off under reduced pressure to obtain a colorless, transparent liquid product with a yield of 87%. No abnormalities were observed after being placed at room temperature for 2 months.

[0099] Example 4

[0100] A boron-containing organosilicon, wherein the raw materials for preparing the boron-containing organosilicon include dimethylsilanediol, methyltrimethoxysilane, dimethyldimethoxysilane, boric acid and cyclohexanone;

[0101] The preparation method of the boron-containing organosilicon comprises:

[0102] A dry round-bottom flask equipped with a mechanical stirrer, a thermometer, and a vacuum device was placed in an oil bath, and 161.30 g of dimethylsilanediol, 30.91 g of boric acid, 85.14 g of methyltrimethoxysilane, 210.38 g of dimethyldimethoxysilane, and 162 g of cyclohexanone were added to the round-bottom flask. The molar ratio of hydroxyl to alkoxy in the reaction system was 0.93:1, and the molar ratio of element B to element Si was 1:8.25. After the materials were uniformly stirred by mechanical stirring at room temperature, the oil bath was heated to 100°C and reacted for 4 hours. Subsequently, the oil temperature was raised to 160°C, and the solvent was removed by distillation under reduced pressure to obtain a colorless, transparent liquid product with a yield of 87%. No abnormalities were observed after standing at room temperature for 2 months.

[0103] Example 5

[0104] A boron-containing organosilicon, wherein the raw materials for preparing the boron-containing organosilicon include dimethylsilanediol, methyltrimethoxysilane, dimethyldimethoxysilane, boric acid and cyclohexanone;

[0105] The preparation method of the boron-containing organosilicon comprises:

[0106] A dry round-bottom flask equipped with a mechanical stirrer, a thermometer, and a vacuum device was placed in an oil bath, and 161.30 g of dimethylsilanediol, 27.82 g of boric acid, 102.17 g of methyltrimethoxysilane, 210.38 g of dimethyldimethoxysilane, and 167 g of cyclohexanone were added to the round-bottom flask. The molar ratio of hydroxyl to alkoxy in the reaction system was 0.84:1, and the molar ratio of element B to element Si was 1:9.4. After the materials were uniformly stirred by mechanical stirring at room temperature, the oil bath was heated to 100°C and reacted for 4 hours. Subsequently, the oil temperature was raised to 160°C, and the solvent was distilled off under reduced pressure to obtain a colorless, transparent liquid product with a yield of 80%. No abnormalities were observed after standing at room temperature for 2 months.

[0107] Example 6

[0108] A boron-containing organosilicon, wherein the raw materials for preparing the boron-containing organosilicon include dimethylsilanediol, methyltrimethoxysilane, dimethyldimethoxysilane, boric acid and cyclohexanone;

[0109] The preparation method of the boron-containing organosilicon comprises:

[0110] A dry round-bottom flask equipped with a mechanical stirrer, a thermometer, and a vacuum device was placed in an oil bath, and 161.30 g of dimethylsilanediol, 23.19 g of boric acid, 102.17 g of methyltrimethoxysilane, 210.38 g of dimethyldimethoxysilane, and 140 g of cyclohexanone were added to the round-bottom flask. The molar ratio of hydroxyl to alkoxy in the reaction system was 0.8:1, and the molar ratio of element B to element Si was 1:11.3. After the materials were uniformly stirred by mechanical stirring at room temperature, the oil bath was heated to 100°C and reacted for 4 hours. Subsequently, the oil temperature was raised to 160°C, and the solvent was distilled off under reduced pressure to obtain a colorless, transparent liquid product with a yield of 72%. No abnormalities were observed after being placed at room temperature for 2 months.

[0111] Comparative Example 1

[0112] A boron-containing organosilicon, wherein the raw materials for preparing the boron-containing organosilicon include dimethylsilanediol, methyltrimethoxysilane, dimethyldimethoxysilane, boric acid and cyclohexanone;

[0113] The preparation method of the boron-containing organosilicon comprises:

[0114] A dry round-bottom flask equipped with a mechanical stirrer, a thermometer, and a vacuum device was placed in an oil bath, and 179.73 g of dimethylsilanediol, 46.37 g of boric acid, 102.17 g of methyltrimethoxysilane, 185.14 g of dimethyldimethoxysilane, and 150 g of cyclohexanone were added to the round-bottom flask. The molar ratio of hydroxyl to alkoxy in the reaction system was 1.15:1, and the molar ratio of element B to element Si was 1:5.7. After the materials were uniformly stirred by mechanical stirring at room temperature, the oil bath was heated to 100°C and reacted for 4 hours. Subsequently, the oil temperature was raised to 160°C, and the solvent was distilled off under reduced pressure to obtain a colorless, transparent liquid product with a yield of 67%. No abnormalities were observed after being placed at room temperature for 2 months.

[0115] Comparative Example 2

[0116] A boron-containing organosilicon, wherein the raw materials for preparing the boron-containing organosilicon include dimethylsilanediol, methyltrimethoxysilane, dimethyldimethoxysilane, boric acid and cyclohexanone;

[0117] The preparation method of the boron-containing organosilicon comprises:

[0118] A dry round-bottom flask equipped with a mechanical stirrer, a thermometer, and a vacuum device was placed in an oil bath, and 211.07 g of dimethylsilanediol, 24.11 g of boric acid, 102.17 g of methyltrimethoxysilane, 210.38 g of dimethyldimethoxysilane, and 160 g of cyclohexanone were added to the round-bottom flask. The molar ratio of hydroxyl to alkoxy in the reaction system was 1:1, and the molar ratio of element B to element Si was 1:12.3. After the materials were uniformly stirred by mechanical stirring at room temperature, the oil bath was heated to 100°C and reacted for 4 hours. Subsequently, the oil temperature was raised to 160°C, and the solvent was distilled off under reduced pressure to obtain a colorless, transparent liquid product with a yield of 75%. No abnormalities were observed after being placed at room temperature for 2 months.

[0119] Comparative Example 3

[0120] A boron-containing organosilicon, wherein the raw materials for preparing the boron-containing organosilicon include dimethylsilanediol, methyltrimethoxysilane, dimethyldimethoxysilane, boric acid and cyclohexanone;

[0121] The preparation method of the boron-containing organosilicon comprises:

[0122] A dry round-bottom flask equipped with a mechanical stirrer, a thermometer, and a vacuum device was placed in an oil bath, and 161.30 g of dimethylsilanediol, 71.10 g of boric acid, 238.39 g of methyltrimethoxysilane, 90.16 g of dimethyldimethoxysilane, and 187 g of cyclohexanone were added to the round-bottom flask. The molar ratio of hydroxyl to alkoxy in the reaction system was 1.03:1, and the molar ratio of element B to element Si was 1:3.7. After the materials were uniformly stirred by mechanical stirring at room temperature, the oil bath was heated to 100°C and reacted for 4 hours. Subsequently, the oil temperature was raised to 160°C, and the solvent was distilled off under reduced pressure to obtain a colorless, transparent liquid product with a yield of 67%. No abnormalities were observed after standing at room temperature for 2 months.

[0123] Comparative Example 4

[0124] A boron-containing organosilicon, wherein the raw materials for preparing the boron-containing organosilicon include dimethylsilanediol, methyltrimethoxysilane, dimethyldimethoxysilane, boric acid and cyclohexanone;

[0125] The preparation method of the boron-containing organosilicon comprises:

[0126] A dry round-bottom flask equipped with a mechanical stirrer, a thermometer, and a vacuum device was placed in an oil bath, and 161.30 g of dimethylsilanediol, 35.55 g of boric acid, 272.44 g of methyltrimethoxysilane, 54.10 g of dimethyldimethoxysilane, and 174 g of cyclohexanone were added to the round-bottom flask. The molar ratio of hydroxyl to alkoxy in the reaction system was 0.76:1, and the molar ratio of element B to element Si was 1:7.3. After the materials were uniformly stirred by mechanical stirring at room temperature, the oil bath was heated to 100°C and reacted for 4 hours. Subsequently, the oil temperature was raised to 160°C, and the solvent was removed by vacuum distillation to obtain a colorless, transparent liquid product with a yield of 64%. After being placed at room temperature for 2 weeks, fogging occurred, which could not meet the optical performance requirements of the optical adhesive.

[0127] Comparative Example 5

[0128] A boron-containing organosilicon, wherein the raw materials for preparing the boron-containing organosilicon include neopentyl glycol, methyltrimethoxysilane, dimethyldimethoxysilane, boric acid and cyclohexanone;

[0129] The preparation method of the boron-containing organosilicon comprises:

[0130] A dry round-bottom flask equipped with a mechanical stirrer, a thermometer, and a vacuum device was placed in an oil bath, and 222.50 g of neopentyl glycol, 22.73 g of boric acid, 102.17 g of methyltrimethoxysilane, 210.38 g of dimethyldimethoxysilane, and 178 g of cyclohexanone were added to the round-bottom flask. The molar ratio of hydroxyl to alkoxy in the reaction system was 0.93:1, and the molar ratio of element B to element Si was 1:6.8. After the materials were uniformly stirred by mechanical stirring at room temperature, the oil bath was heated to 100°C and reacted for 4 hours. Subsequently, the oil temperature was raised to 160°C, and the solvent was distilled off under reduced pressure to obtain a colorless, transparent liquid product with a yield of 65%. No abnormalities were observed after standing for 2 months.

[0131] The preparation method of the boron-containing organosilicon provided by the present invention is simple, does not require the addition of a catalyst, is colorless and transparent, and has no adverse phenomena such as fogging and precipitation after storage for 2 months, with a yield of 72-87%. However, in Comparative Example 4, since the molar ratio of hydroxyl to alkoxy in the reaction system is 0.76:1, although a colorless and transparent boron-containing organosilicon can be obtained, the residual alkoxy absorbs moisture in the air and undergoes a hydrolysis reaction, causing the boron-containing organosilicon to become foggy and turbid after storage for 14 days, and has poor storage stability and cannot be used in optical adhesives; Comparative Example 5 uses fatty alcohol instead of silanol, and the fatty alcohol has poor compatibility with siloxane monomers and boric acid compounds. After addition, the reactor becomes turbid and foggy, the reaction degree is low, and the product yield is only 65%.

[0132] The sources of the raw materials and equipment used in the following application examples and comparative examples are as follows:

[0133] (A) Vinyl silicone oil

[0134]

[0135] (B) Vinyl silicone resin

[0136] code name supplier model Viscosity (mPa·s) Vinyl content (mmol / g) B-1 Delta Silicone DT-10050 10000 0.4444

[0137] (C) Hydrogenated silicone oil

[0138] code name Manufacturer Brand Silicon hydride content (mmol / g) C-1 Anhui Aiyota Silicone Oil Co., Ltd. IOTA203 0.18

[0139] (D) Hydrogenated silicone resin

[0140] The general formula is: (HMe2SiO 1 / 2 ) x (HMeSiO 2 / 2 ) y (MeSiO 3 / 2 ) z , wherein Me is a methyl group.

[0141]

[0142] (E) Catalyst

[0143] code name supplier model E-1 Anhui Aiyota Silicone Oil Co., Ltd. IOTAPC16

[0144] (F) Inhibitors

[0145] code name supplier model F-1 Guangzhou Xiyi Chemical CEYZ

[0146] coating equipment

[0147] code name Manufacturer model coating machine Shangwang Printing Machinery Co., Ltd. THVG-1100

[0148] Application Example 1

[0149] An optical adhesive, wherein the raw materials for preparing the optical adhesive include 127 parts by weight of vinyl silicone resin B, 140 parts by weight of vinyl silicone oil A, 15 parts by weight of hydrogenated silicone oil C, 123 parts by weight of hydrogenated silicone resin D, 4.4 parts by weight of the boron-containing organosilicon provided in Example 1, 10.1 parts by weight of catalyst E, and 10.5 parts by weight of inhibitor F;

[0150] The preparation method of the optical adhesive comprises:

[0151] Vinyl silicone resin B-1, vinyl silicone oil A-1, hydrogenated silicone oil C-1, hydrogenated silicone resin D-1, the boron-containing organosilicon provided in Example 1, catalyst E-1, and inhibitor F-1 were mixed, stirred evenly, and vacuum degassed to obtain the optical adhesive;

[0152] The optical adhesive is used to prepare the organosilicon OCA, and the specific method is as follows:

[0153] The optical adhesive was coated on a non-silicone release film (75 μm thick, 30 gf / 25 mm release force) by knife coating to a thickness of 250 μm, and then thermally cured (curing conditions were 60°C, 10 min). A fluorine release film (50 μm thick, 13 gf / 25 mm release force) was then adhered to the side of the optical adhesive layer away from the non-silicone release film to obtain the silicone OCA.

[0154] Application Examples 2-6, Comparative Application Examples 1-3

[0155] An optical adhesive and a preparation method thereof, which differs from Application Example 1 only in that the boron-containing organosilicon provided in Example 1 is replaced in equal amounts by the boron-containing organosilicon provided in Examples 2-6 and Comparative Examples 1-3, and the remaining raw materials, process parameters, and steps are the same as those in Application Example 1;

[0156] The optical adhesive is used to prepare an organosilicon OCA, and the preparation method of the organosilicon OCA is the same as that of Application Example 1.

[0157] Comparative Application Example 4

[0158] An optical adhesive and a preparation method thereof, which differs from Application Example 1 only in that an equal amount of the boron-containing organosilicon provided in Example 1 is replaced with a silane coupling agent KH-560, and the remaining raw materials, process parameters, and steps are the same as those in Application Example 1;

[0159] The optical adhesive is used to prepare an organosilicon OCA, and the preparation method of the organosilicon OCA is the same as that of Application Example 1.

[0160] Application Comparative Example 5

[0161] An optical adhesive and a preparation method thereof, which differ from Application Example 1 only in that an equal amount of the boron-containing organosilicon provided in Example 1 is replaced by the boron-containing organosilicon provided in Comparative Example 5, and the remaining raw materials, process parameters, and steps are the same as those in Application Example 1; due to the large difference in refractive index between the boron-containing organosilicon provided in Comparative Example 5 and the organosilicon polymer, severe fogging occurs during the preparation of the optical adhesive, which does not meet the requirements of an optical adhesive.

[0162] Performance Testing

[0163] (1) Peeling force test: One side of the optical adhesive layer of the organic silicon OCA provided in the application example and the comparative example was attached to the substrate, and the other side was attached to the PET original film (purchased from Hefei Lucky Technology, with a thickness of 100 μm) to form a PET-organic silicon OCA-substrate composite structure, which was placed on an electric roller machine (Beidou Instrument, PT-509) and rolled once with a 3 kg roller at a speed of 10 mm / s to obtain a peeling specimen of the corresponding substrate; after the sample was prepared, the 180° peeling force at different placement times was tested according to GB / T2792-2014.

[0164] (2) Light transmittance and haze test: Test in accordance with GB / T 24107.1;

[0165] (3) Glass transition temperature: tested by Hitachi DSC200;

[0166] The organosilicon OCA provided by Application Examples 1-6 and Comparative Application Examples 1-4 were tested according to the above method. The test results are shown in Tables 1 and 2 below:

[0167] Table 1

[0168]

[0169] Table 2

[0170]

[0171] The test data in the table show that controlling the molar ratio of B to Si in the boron-containing organosilicon raw materials within the range of 1:(5-11.5) enables the organosilicon OCA to exhibit good adhesion to substrates such as ink, glass, and polarizers, and also exhibits excellent hydrolysis resistance. Compared to the silane coupling agent commonly used as a tackifier in current organosilicon OCAs, the organosilicon OCAs provided in Application Examples 1-6 exhibit varying degrees of improved adhesion to ink, glass, and polarizer substrates. The initial peel force is greater than 2N / 25mm, and the peel force increases rapidly, reaching the final value in 5 minutes. The final peel force for ink, glass, and polarizers can reach a maximum of approximately 22N / 25mm. Furthermore, after double 85 aging, the haze changes little, and the performance is excellent in high temperature and high humidity resistance.

[0172] The molar ratio of B to Si in the preparation raw materials of the boron-containing organosilicon used in Application Examples 2-6 is in the range of 1: (6.5-11.5), and the improvement effect of the adhesion performance of organosilicon OCA on ink, glass, and polarizer substrates is particularly prominent. Application Comparative Example 4 uses KH-560 as a tackifier. The peeling force of the organosilicon OCA increases slowly after lamination. The peeling force of the polarizer can only reach the final peeling force of 2.44N / 25mm after 96 hours. The peeling force of the glass and ink both need to be placed for 48 hours to reach the final peeling force, which are 13.8N / 25mm and 3.57N / 25mm, respectively. In addition, the glass transition temperature of the organosilicon OCA provided by the present invention is below -40°C, and it has excellent low-temperature resistance, which can meet the use requirements of different scenarios.

[0173] The molar ratio of hydroxyl to alkoxy in the raw materials for preparing the boron-containing organosilicon used in Comparative Example 1 is 1.15:1. The OH content in the raw materials for preparing the boron-containing organosilicon is too high, which increases the possibility of boric acid being exposed at the end. The boron-containing organosilicon is easily attacked by water vapor and fogs. The hydrolysis resistance of silicone OCA is poor, and it will absorb water vapor in the air, causing the film to fog.

[0174] The molar ratios of B to Si in the raw materials for the boron-containing organosilicon used in Application Comparative Example 2 and Application Comparative Example 3 are 1:12.3 and 1:3.7, respectively. If the B content in the raw materials for the boron-containing organosilicon is too low, the bonding performance will deteriorate significantly. If the B content is too high, the hydrolysis resistance of the organosilicon OCA will be poor, and it will absorb water vapor in the air, causing the film to fog.

[0175] The applicant declares that while the present invention uses the aforementioned embodiments and application examples to illustrate the boron-containing organosilicon, optical adhesive, organosilicon OCA, and their preparation methods and applications, the present invention is not limited to these embodiments and application examples. This does not imply that the present invention must rely on these embodiments and application examples for implementation. Those skilled in the art should understand that any improvements to the present invention, equivalent replacements for various raw materials in the present invention's products, addition of auxiliary components, and selection of specific methods, etc., fall within the scope of protection and disclosure of the present invention.

Claims

1. A boron-containing organosilicon, characterized in that: The raw materials for preparing the boron-containing organosilicon include a combination of silanol, siloxane monomer, boric acid compound and solvent; In the raw material for preparing the boron-containing organosilicon, the ratio of the total molar amount of hydroxyl groups to the total molar amount of alkoxy groups is (0.8-1.1):1, and the ratio of the total molar amount of the B element to the total molar amount of the Si element is 1:(5-11.5); The silanol is dimethylsilanediol; The siloxane monomers are methyltrimethoxysilane and dimethyldimethoxysilane; The boric acid compound includes any one of boric acid, phenylboric acid or tetrahydroxyboron or a combination of at least two thereof; The molar ratio of the hydroxyl group in the boric acid compound to the hydroxyl group in the silanol is 1:(1-7); The boron-containing organosilicon is prepared by the following method, which comprises the following steps: Silanol, siloxane monomers and boric acid compounds react in the presence of a solvent to obtain the boron-containing organosilicon; The reaction temperature is 80-140°C.

2. The boron-containing organosilicon according to claim 1, characterized in that In the raw materials for preparing the boron-containing organosilicon, the ratio of the total molar amount of the B element to the total molar amount of the Si element is 1:(6.5-11.5).

3. The boron-containing organosilicon according to claim 2, characterized in that In the raw material for preparing the boron-containing organosilicon, the ratio of the total molar amount of the B element to the total molar amount of the Si element is 1:(7-8.5).

4. The boron-containing organosilicon according to claim 1, characterized in that The solvent includes any one or a combination of at least two of N,N-dimethylformamide, dimethyl sulfoxide, methanol, acetonitrile, isopropyl alcohol, 1,4-dioxane or cyclohexanone.

5. The boron-containing organosilicon according to claim 1, characterized in that Based on the total mass of the silanol, siloxane monomer and boric acid compound being 100%, the mass of the solvent is 25-40%.

6. A method for preparing boron-containing organosilicon according to any one of claims 1 to 5, characterized in that: The preparation method comprises: Silanol, siloxane monomers and boric acid compounds react in the presence of a solvent to obtain the boron-containing organosilicon; The reaction temperature is 80-140°C.

7. The preparation method according to claim 6, characterized in that The reaction time is 3-7h.

8. The preparation method according to claim 6, characterized in that After the reaction is completed, the step of reduced pressure distillation is further included.

9. A use of the boron-containing organosilicon according to any one of claims 1 to 5, characterized in that: The boron-containing organosilicon is used as a tackifier in optical adhesives.

10. An optical adhesive, characterized in that: In parts by weight, the raw materials for preparing the optical adhesive include: 10-30 parts by weight of vinyl silicone resin 30-50 parts by weight of vinyl silicone oil 5-20 parts by weight of hydrogenated silicone oil 10-30 parts by weight of hydrogenated silicone resin 0.01-0.5 parts by weight of catalyst 0.1-15 parts by weight of the boron-containing organosilicon according to any one of claims 1 to 5.

11. The optical adhesive according to claim 10, characterized in that The vinyl silicone resin includes any one of vinyl MQ silicone resin, vinyl MDT silicone resin, vinyl MTQ silicone resin or vinyl DT silicone resin, or a combination of at least two thereof.

12. The optical adhesive according to claim 10, wherein The viscosity of the vinyl silicone resin at 25° C. is 5000-50000 mPa·s.

13. The optical adhesive according to claim 10, wherein The vinyl content of the vinyl silicone resin is 0.3-1.0 mmol / g.

14. The optical adhesive according to claim 10, characterized in that The vinyl silicone oil includes any one or a combination of at least two of silicone oil containing vinyl groups at the terminal, silicone oil containing vinyl groups at the side groups, and silicone oil containing vinyl groups at both the terminal and the side groups.

15. The optical adhesive according to claim 10, wherein The viscosity of the vinyl silicone oil at 25° C. is 100-20000 mPa·s.

16. The optical adhesive according to claim 10, characterized in that The vinyl content of the vinyl silicone oil is 0.1-0.75 mmol / g.

17. The optical adhesive according to claim 10, wherein The general formula of the hydrogenated silicone resin is (R 21 R 22 R 23 SiO 1 / 2 ) x (R 24 R 25 SiO 2 / 2 ) y (R 26 SiO 3 / 2 ) z ; Among them, R 21 、R 22 、R 23 、R 24 、R 25 、R 26 are independently selected from any one of a hydrogen atom, a C1-C5 straight chain or branched alkyl group, and R 21 、R 22 、R 23 、R 24 、R 25 、R 26 At least one of them is a hydrogen atom; x:y:z=1:(0.2-0.3):(2-3).

18. The optical adhesive according to claim 10, wherein The viscosity of the hydrogenated silicone resin at 25° C. is 10,000-40,000 mPa·s.

19. The optical adhesive according to claim 10, wherein The silicon hydrogen content of the hydrogen-containing silicone resin is 0.1-1.2 mmol / g.

20. The optical adhesive according to claim 10, wherein The general formula of the hydrogen-containing silicone oil is (R 31 R 32 R 33 SiO 1 / 2 ) p (R 34 R 35 SiO 2 / 2 ) m (R 36 R 37 SiO 2 / 2 ) n ; Among them, R 31 、R 32 、R 33 、R 34 、R 35 、R 36 、R 37 are independently selected from any one of a hydrogen atom, a C1-C5 straight chain or branched alkyl group, and R 34 、R 35 、R 36 、R 37 At least one of them is a hydrogen atom; 1≤p≤2, 0≤m≤50, 0≤n≤50, and m and n are not 0 at the same time.

21. The optical adhesive according to claim 10, wherein The viscosity of the hydrogen-containing silicone oil at 25° C. is 100-3000 mPa·s.

22. The optical adhesive according to claim 10, wherein The silicon hydrogen content of the hydrogen-containing silicone oil is 0.05-0.5 mmol / g.

23. The optical adhesive according to claim 10, wherein In the raw materials for preparing the optical adhesive, the ratio of the total molar amount of vinyl groups to the total molar amount of silyl groups is (0.95-1.05):

1.

24. The optical adhesive according to claim 10, wherein The catalyst includes any one of chloroplatinic acid, Karstedt platinum catalyst or Willing platinum catalyst, or a combination of at least two thereof.

25. The optical adhesive according to claim 10, wherein The raw materials for preparing the optical adhesive further include 0.2-0.5 parts by weight of an inhibitor.

26. The optical adhesive according to claim 25, characterized in that The inhibitor includes an alcohol compound containing an unsaturated group and / or a siloxane containing at least two vinyl groups.

27. The optical adhesive according to claim 25, characterized in that The inhibitor includes any one of 1,4-butynediol, ethynylcyclohexanol, tetramethyltetravinylcyclotetrasiloxane or 2-methyl-3-butyn-2-ol, or a combination of at least two thereof.

28. An organosilicon OCA, characterized in that: The organic silicon OCA comprises a first release film, an optical adhesive layer, and a second release film stacked in sequence; the optical adhesive layer is formed by curing the optical adhesive according to any one of claims 10 to 27.

29. The organosilicon OCA according to claim 28, characterized in that The thickness of the optical adhesive layer is 20-2000 μm.

30. The organosilicon OCA according to claim 28, characterized in that The thickness of the first release film and the second release film are independently 50-200 μm.

31. The organosilicon OCA according to claim 28, characterized in that The release force difference between the first release film and the second release film is 15-20 gf / 25 mm.

32. Use of the optical adhesive according to any one of claims 10 to 27 or the organosilicon OCA according to any one of claims 28 to 31 in display bonding.

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