Blue light blocking compound, blue light blocking composition, use of blue light blocking compound, use of blue light blocking composition, and method for preparing blue light blocking compound

Abstract

Provided are a blue light blocking compound and a use thereof, a blue light blocking composition and a use thereof, and a method for preparing a blue light blocking compound.SOLUTION: The blue light blocking compound is represented by Formula 1 below. In Formula 1, R1 and R8 are each independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, halogen, N (R1a) 2, OR1b, SR1c, S0 2 R 1d, C0R 1e, N0 2, CN, S0R 1h, a 5-membered heterocyclic ring, a 6-membered heterocyclic ring, or a fused ring structure formed by connecting R1 and R8.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present disclosure relates to blue light blocking compounds, blue light blocking compositions, uses of blue light blocking compounds, uses of blue light blocking compositions, and methods for making blue light blocking compounds. [Background technology]

[0002] Visible light is electromagnetic radiation with wavelengths between 380nm and 780nm, and electromagnetic radiation with wavelengths between 380nm and 500nm can be broadly referred to as blue light. Excessive exposure to blue light can have harmful health effects, including retinal cell damage, macular degeneration, eye strain, glare, and the progression of age-related eye diseases. Therefore, it is very important to prevent excessive blue light from entering the eyes.

[0003] Using an ophthalmic device capable of blocking blue light (also known as a blue-light-blocking ophthalmic device) is one way to effectively avoid the harmful health effects caused by blue light. When placed on the surface of a user's eye, the blue-light-blocking ophthalmic device can block (e.g., absorb or reflect) at least a portion of blue light, thereby reducing the amount of blue light entering the eye. Blue-light-blocking ophthalmic devices are manufactured by incorporating blue-light-blocking compounds into the materials of the ophthalmic device. However, existing blue-light-blocking compounds have poor reactivity and miscibility with the materials of ophthalmic devices, resulting in insufficient blue-light blocking effects. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Taiwan Patent No. 793944 Summary of the Invention

[0005] The present disclosure provides blue light blocking compounds, blue light blocking compositions comprising the blue light blocking compounds, uses of the blue light blocking compounds in the manufacture of ophthalmic devices, optical films, screen protectors, displays, etc., uses of the blue light blocking compositions in the manufacture of ophthalmic devices, optical films, screen protectors, displays, etc., and methods for manufacturing the blue light blocking compounds. The blue light blocking compounds exhibit good reactivity and miscibility, and therefore, products such as ophthalmic devices, optical films, screen protectors, or displays formed with the blue light blocking compounds of the present disclosure can exhibit good blue light blocking effects.

[0006] According to an embodiment, a blue light blocking compound is provided. The blue light blocking compound is represented by the following formula 1. In formula 1, R1 and R8 each independently represent H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, an alkenyl group substituted with a halogen, a halogen, N(R 1a )2, OR 1b , S.R. 1c , SO2R 1d , C.O.R. 1e , NO2, CN, SOR 1h , a 5-membered heterocycle, a 6-membered heterocycle, or a fused ring structure formed by connecting R1 and R8, and R 1a and R 1b are each independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted phenyl group; R 1d is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or OH; R 1e is H, OH, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or -OR 1f and R 1c , R 1f , and R 1hare each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted alkenyl group, R2 is H or a substituted or unsubstituted C1-C4 alkyl group, and R3 is X-(C n H 2n O m ) p wherein X is O, NH, S, or SO2, m is 1 to 4, n is 1 to 4, p is 1 to 4, R4 is CN or C(O)R6, and R6 is H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, R3-C(O)-CCH2R5, or OR 1g and R 1g is a substituted or unsubstituted C1 to C4 alkyl group or a substituted or unsubstituted C1 to C4 alkenyl group, and R5 is H or a substituted or unsubstituted C1 to C4 alkyl group. [ka]

[0007] According to another embodiment, a blue light blocking composition is provided. The blue light blocking composition includes a blue light blocking compound represented by the above formula 1 and a polymerizable monomer. In formula 1, R1 and R8 each independently represent H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a halogen, N(R 1a )2, OR 1b , S.R. 1c , SO2R 1d , C.O.R. 1e , NO2, CN, SOR 1h , a 5-membered heterocycle, a 6-membered heterocycle, or a fused ring structure formed by connecting R1 and R8, and R 1a and R 1b are each independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted phenyl group; R 1d is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or OH; R 1eis H, OH, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or -OR 1f and R 1c , R 1f , and R 1h are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted alkenyl group, R2 is H or a substituted or unsubstituted C1-C4 alkyl group, and R3 is X-(C n H 2n O m ) p wherein X is O, NH, S, or SO2, m is 1 to 4, n is 1 to 4, p is 1 to 4, R4 is CN or C(O)R6, and R6 is H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, R3-C(O)-CCH2R5, or OR 1g and R 1g is a substituted or unsubstituted C1 to C4 alkyl group or a substituted or unsubstituted C1 to C4 alkenyl group, and R5 is H or a substituted or unsubstituted C1 to C4 alkyl group.

[0008] According to yet another embodiment, there is provided a use of the blue light blocking compound for use in the manufacture of an ophthalmic device.

[0009] According to yet another embodiment, there is provided a use of a blue light blocking composition. The blue light blocking composition is used for manufacturing an optical film, a screen protector, a display, or an ophthalmic device. The blue light blocking composition includes a blue light blocking compound represented by the above formula 1 and a polymerizable monomer. In formula 1, R1 and R8 each independently represent H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a halogen, N(R 1a )2, OR 1b , S.R. 1c , SO2R 1d , C.O.R. 1e , NO2, CN, SOR 1h, a 5-membered heterocycle, a 6-membered heterocycle, or a fused ring structure formed by connecting R1 and R8, and R 1a and R 1b are each independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted phenyl group; R 1d is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or OH; R 1e is H, OH, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or -OR 1f and R 1c , R 1f , and R 1h are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted alkenyl group, R2 is H or a substituted or unsubstituted C1-C4 alkyl group, and R3 is X-(C n H 2n O m ) p wherein X is O, NH, S, or SO2, m is 1 to 4, n is 1 to 4, p is 1 to 4, R4 is CN or C(O)R6, and R6 is H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, R3-C(O)-CCH2R5, or OR 1g and R 1g is a substituted or unsubstituted C1 to C4 alkyl group or a substituted or unsubstituted C1 to C4 alkenyl group, and R5 is H or a substituted or unsubstituted C1 to C4 alkyl group.

[0010] According to yet another embodiment, there is provided a method for preparing a blue light blocking compound, the method comprising the steps of: providing a compound represented by the following formula 2; hydrolyzing the compound to obtain an intermediate product; and esterifying the intermediate product to obtain the blue light blocking compound. In formula 2, R1 and R8 each independently represent H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a halogen, N(R 1a )2, OR 1b , S.R. 1c , SO2R1d , C.O.R. 1e , NO2, CN, SOR 1h , a 5-membered heterocycle, a 6-membered heterocycle, or a fused ring structure formed by connecting R1 and R8, and R 1a and R 1b are each independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted phenyl group; R 1d is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or OH; R 1e is H, OH, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or -OR 1f and R 1c , R 1f , and R 1h are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted alkenyl group, R2 is H or a substituted or unsubstituted C1-C4 alkyl group, R4' is CN or C(O)R6', R6' is H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or OR 1j and R 1j is a substituted or unsubstituted C1 to C4 alkyl group or a substituted or unsubstituted C1 to C4 alkenyl group. [ka]

[0011] These and other embodiments of the present disclosure will be better understood with reference to the following detailed description of non-limiting embodiments. DETAILED DESCRIPTION OF THE INVENTION

[0012] As used herein, the term "ophthalmic device" refers to a device that is placed on the surface of the eye, which may or may not be in direct contact with the surface of the eye. Ophthalmic devices can have functions such as vision correction, disease treatment, drug delivery, and appearance change. Ophthalmic devices include, but are not limited to, soft contact lenses and hard contact lenses. Soft contact lenses include, but are not limited to, hydrogel contact lenses and silicone hydrogel contact lenses. As used herein, the term "hydrogel contact lens" refers to a contact lens that does not contain silicone groups in its structure. As used herein, the term "silicone hydrogel contact lens" refers to a contact lens that contains silicone groups in its structure.

[0013] As used herein, the term "use in the manufacture of an ophthalmic device" may mean that a blue light blocking compound or composition according to the present disclosure is added to the material of an ophthalmic device, or that a blue light blocking compound or composition according to the present disclosure is attached to the surface of an ophthalmic device. The present disclosure is not limited thereto.

[0014] In this specification, if it is not specified whether a group is substituted, the group may refer to a substituted or unsubstituted group. For example, an "alkyl group" may refer to a substituted or unsubstituted alkyl group, an "alkenyl group" may refer to a substituted or unsubstituted alkenyl group, and a "phenyl group" may refer to a substituted or unsubstituted phenyl group. In addition, "C x When " is used to describe a group, it means that the backbone of the group has x carbon atoms.

[0015] Herein, the structure of a compound may be represented by a skeletal formula. In this representation, carbon atoms, hydrogen atoms, and carbon-hydrogen bonds may be omitted. Of course, when a functional group is explicitly indicated in a structure, the structure will remain as drawn. Herein, when a benzene ring contains a line extending from the inside to the outside of the benzene ring, with one end of this line connected to a group, this means that the substitution site of this group on the benzene ring is indefinite, and structures formed by substituting this group for atoms at different sites on the benzene ring are within the scope of the present disclosure.

[0016] The present disclosure provides blue light blocking compounds represented by Formula 1: [ka]

[0017] In Formula 1, R1 and R8 each independently represent H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a halogen, N(R 1a )2, OR 1b , S.R. 1c , SO2R 1d , C.O.R. 1e , NO2, CN, SOR 1h , a 5-membered heterocycle, a 6-membered heterocycle, or a fused ring structure formed by connecting R1 and R8, and R 1a and R 1b are each independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted phenyl group; R 1d is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or OH; R 1e is H, OH, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or -OR 1f and R 1c , R 1f , and R 1hare each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted alkenyl group, R2 is H or a substituted or unsubstituted C1-C4 alkyl group, and R3 is X-(C n H 2n O m ) p wherein X is O, NH, S, or SO2, m is 1 to 4, n is 1 to 4, p is 1 to 4, R4 is CN or C(O)R6, and R6 is H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, R3-C(O)-CCH2R5, or OR 1g and R5 is H or a substituted or unsubstituted C1-C4 alkyl group, and R 1g is a substituted or unsubstituted C1 to C4 alkyl group, or a substituted or unsubstituted C1 to C4 alkenyl group.

[0018] In one embodiment, in Formula 1, R and R are each independently H, an unsubstituted alkyl group, an alkyl group substituted with a halogen, a halogen, N(R 1a )2, OR 1b , S.R. 1c , SO2R 1d , C.O.R. 1e , NO2, CN, SOR 1h , a 5-membered heterocycle, a 6-membered heterocycle, or a fused ring structure formed by connecting R1 and R8, and R 1a and R 1b are each independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted phenyl group; R 1d is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or OH; R 1e is H, OH, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or -OR 1f and R 1c , R 1f and R 1h are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted alkenyl group, R2 is H or a substituted or unsubstituted C1-C4 alkyl group, and R3 is X-(Cn H 2n O m ) p wherein X is O, NH, S, or SO2, m is 1 to 4, n is 1 to 4, p is 1 to 4, R4 is CN or C(O)R6, and R6 is H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, R3-C(O)-CCH2R5, or OR 1g R5 is H or a substituted or unsubstituted C1-C4 alkyl group, and R 1g is a substituted or unsubstituted C1 to C4 alkyl group, or a substituted or unsubstituted C1 to C4 alkenyl group.

[0019] In an embodiment, in Formula 1, R1 and R8 are each independently H, an unsubstituted C1-C4 alkyl group, a C1-C4 alkyl group substituted with a halogen, an unsubstituted C1-C4 alkenyl group, a C1-C4 alkenyl group substituted with a halogen, a halogen, N(R 1a )2, OR 1b , S.R. 1c , SO2R 1d , C.O.R. 1e , NO2, CN, SOR 1h , a 5-membered heterocycle, a 6-membered heterocycle, or a fused ring structure formed by connecting R1 and R8.

[0020] In an embodiment, in Formula 1, R1 and R8 are each independently H, an unsubstituted C1-C4 alkyl group, a C1-C4 alkyl group substituted with a halogen, an unsubstituted C1-C4 alkenyl group, a C1-C4 alkenyl group substituted with a halogen, a halogen, N(R 1a )2, OR 1b , S.R. 1c , SO2R 1d , C.O.R. 1e , NO2, CN, SOR 1h, a heterocycle represented by the following formula 3, a heterocycle represented by the following formula 4, or a heterocycle represented by the following formula 5. The heterocycle represented by the following formula 3, the heterocycle represented by the following formula 4, and the heterocycle represented by the following formula 5 are connected to the benzene ring of formula 1 through their N atoms. In an embodiment, R and R can be connected to form a fused ring structure represented by the following formula 6 or formula 7 (the fused ring structure represented by formula 6 or formula 7 includes the benzene ring shown in formula 1). [ka] [ka] [ka] [ka] [ka]

[0021] In embodiments, in Formula 1, R and R are each independently H, an unsubstituted alkyl group, an alkyl group substituted with a halogen, an unsubstituted alkenyl group, an alkenyl group substituted with a halogen, a halogen, N(R 1a )2, OR 1b , SOR 1h , a 5-membered heterocycle, a 6-membered heterocycle, or a fused ring structure formed by connecting R1 and R8, and R 1a and R 1b are each independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted phenyl group; R 1h is a substituted or unsubstituted alkyl group.

[0022] In an embodiment, in Formula 1, R1 and R8 are each independently H, an unsubstituted C1-C4 alkyl group, a C1-C4 alkyl group substituted with a halogen, an unsubstituted C1-C4 alkenyl group, a C1-C4 alkenyl group substituted with a halogen, a halogen, N(R 1a )2, OR 1b , SOR 1h , a 5-membered heterocycle, a 6-membered heterocycle, or a fused ring structure formed by connecting R1 and R8, and R 1a and R 1b are each independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted phenyl group; R 1h is a substituted or unsubstituted alkyl group.

[0023] In an embodiment, in Formula 1, R1 and R8 are each independently selected from H, a C1-C4 alkyl group substituted with F, a C1-C4 alkenyl group substituted with F, a halogen, N(R 1a )2, OR 1b , SOR 1h , a 5-membered heterocycle, a 6-membered heterocycle, or a fused ring structure formed by connecting R1 and R8, and R 1a and R 1b are each independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted phenyl group; R 1h is a substituted or unsubstituted alkyl group.

[0024] In embodiments, in Formula 1, R3 is X—(C n H 2n O m ) p wherein X is O or NH, m is 1 to 3, n is 1 to 3, and p is 1 to 3.

[0025] In embodiments, in Formula 1, R3 is X—(C n H 2n O m ) p wherein X is O or NH, m is 1 to 2, n is 1 to 2, and p is 1 to 2.

[0026] In embodiments, in Formula 1, R4 is C(O)R6, where R6 is H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, R3-C(O)-CCH2R5, or OR 1g and R5 and R 1g is defined as above.

[0027] In embodiments, in Formula 1, R4 is C(O)R6, and R6 is an alkyl group, an alkenyl group, or R3-C(O)-CCH2R5, or OR 1g and R5 and R 1g is defined as above.

[0028] In an embodiment, the "substituted or unsubstituted alkyl group" in the above formula 1 can refer to a substituted or unsubstituted C1 to C4 alkyl group. In an embodiment, the "substituted or unsubstituted alkenyl group" in the above formula 1 can refer to a substituted or unsubstituted C1 to C4 alkenyl group.

[0029] In embodiments, the blue light blocking compound can be represented by any one of the following formulas 1-1 to 1-9: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0030] A method for producing a blue light blocking compound according to the present disclosure can include the following steps.

[0031] Compounds are provided that are represented by the following formula 2: In formula 2, R1, R8, and R2 are defined as above. In formula 2, R4' is CN or C(O)R6', where R6' is H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or OR 1j and R 1j is a substituted or unsubstituted C1-C4 alkyl group or a substituted or unsubstituted C1-C4 alkenyl group. The compound is hydrolyzed to obtain an intermediate product. In an embodiment, the compound, an alkaline reagent, a solvent, and water are mixed and subjected to a hydrolysis reaction, followed by extraction with ethyl acetate to obtain the intermediate product. The alkaline reagent may be at least one selected from the group consisting of sodium carbonate, potassium carbonate, potassium hydroxide, and sodium hydroxide. The solvent may be at least one selected from the group consisting of acetone, tetrahydrofuran, methanol, ethanol, n-propanol, isopropanol, methylene chloride, and ethyl acetate.

[0032] For example, the water used in the above steps can be purified water, filtered water, distilled water, electrolyzed water, and the like. [ka]

[0033] In an embodiment, the compound represented by the following formula 2 may be a compound represented by the following formula 2-1. [ka]

[0034] In an embodiment, the compound represented by the following formula 2 may be a compound represented by the following formula 2-2. [ka]

[0035] In an embodiment, the compound represented by the following formula 2 may be a compound represented by the following formula 2-3. [ka]

[0036] The intermediate product is then esterified to obtain the blue light-blocking compound represented by Formula 1. In an embodiment, the intermediate product, the hydrophilic compound, and the solvent are mixed and subjected to an esterification reaction to obtain the blue light-blocking compound represented by Formula 1. The hydrophilic compound is an acrylic ester compound containing a hydroxyl group. The hydrophilic compound may be at least one selected from the group consisting of 2-hydroxyethyl methacrylate (HEMA), 4-hydroxybutyl acrylate (HBA), glycidyl methacrylate (GMA), hydroxypropyl methacrylate (HPMA), 2-hydroxyisopropyl methacrylate (HIPMA), and hydroxybutyl methacrylate (HBMA). The solvent may be at least one selected from the group consisting of acetone, tetrahydrofuran, methanol, ethanol, n-propanol, isopropanol, methylene chloride, and ethyl acetate.

[0037] The blue light-blocking compounds of the present disclosure can be used to manufacture ophthalmic devices, optical films, screen protectors, or displays. The blue light-blocking compounds of the present disclosure can be used to prepare blue light-blocking compositions, which can be used to manufacture ophthalmic devices, optical films, screen protectors, or displays. The blue light-blocking compositions can include a blue light-blocking compound and a polymerizable monomer. In embodiments, the polymerizable monomer can include a monomer containing an alkenyl group or a hydrophilic monomer containing an alkenyl group and hydrophilic properties.

[0038] In embodiments, the blue light blocking compounds of the present disclosure can be used to prepare blue light blocking compositions, which can be used to manufacture ophthalmic devices. The blue light blocking compositions for manufacturing ophthalmic devices include a blue light blocking compound and a polymerizable monomer. The polymerizable monomer can include at least one of a hydrophilic monomer, a first siloxane monomer, and a second siloxane monomer. The polymerizable monomer can be at least one selected from the group consisting of a hydrophilic monomer, a first siloxane monomer, and a second siloxane monomer. The first siloxane monomer is different from the second siloxane monomer. In embodiments, the polymerizable monomer includes a hydrophilic monomer. In embodiments, the polymerizable monomer consists of a hydrophilic monomer. In embodiments, the polymerizable monomer includes a hydrophilic monomer and a first siloxane monomer. In embodiments, the polymerizable monomer consists of a hydrophilic monomer and a first siloxane monomer. In embodiments, the polymerizable monomer includes a hydrophilic monomer and a second siloxane monomer. In embodiments, the polymerizable monomer comprises a hydrophilic monomer and a second siloxane monomer. In embodiments, the polymerizable monomer comprises a hydrophilic monomer, a first siloxane monomer, and a second siloxane monomer. In embodiments, the polymerizable monomer comprises a hydrophilic monomer, a first siloxane monomer, and a second siloxane monomer.

[0039] <Hydrophilic Monomer> The hydrophilic monomer can be at least one selected from the group consisting of 2-hydroxyethyl methacrylate (HEMA), methyl methacrylate (MMA), methacrylic acid (MAA), N-vinylpyrrolidone (NVP), N,N-dimethylacrylamide (DMA), 4-acryloylmorpholine (AcMO), 2-hydroxyethyl acrylamide (HEAA), glycidyl methacrylate (GMA), glycerol monomethacrylate (GMMA), acrylic acid (AA), N,N-di(methylmethacrylamide) (DMA), hexafluoroisopropyl methacrylate (HFMA), N-vinyl-N-methylacetamide, glycine vinyl carbonate, 2-methacryloyloxyethyl phosphorylcholine, and 2-hydroxybutyl methacrylate.

[0040] The blue light blocking compound may be present in an amount ranging from about 0.1% by weight to about 30% by weight based on the total weight of the blue light blocking composition, but the present disclosure is not limited thereto. The content of the blue light blocking compound can be adjusted according to the required blue light blocking rate of the blue light blocking product.

[0041] <First siloxane monomer> The first siloxane monomer contains a single methacryloyl group, which can be represented as CH2=C(CH3)CO-, or alternatively, the methacryloyl group can be represented as: [ka] It can also be expressed as:

[0042] The first siloxane monomer can be at least one selected from the group consisting of Formulae A to H below. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0043] In Formula B, a = 4 to 80. In Formula C, b = 4 to 80, c = 3 to 40. In Formula D, d = 2 to 40, e = 2 to 40. In Formula E, f = 2 to 40, g = 2 to 40. In Formula F, h = 4 to 80. In Formula G, i = 4 to 80. In Formula H, TMS is an abbreviation for trimethylsiloxy.

[0044] <Second Siloxane Monomer> The second siloxane monomer contains two methacryloyl groups, which can be represented as CH2=C(CH3)CO-, or alternatively, the methacryloyl groups can be represented as: [ka] It can also be expressed as:

[0045] The second siloxane monomer can be at least one selected from the group consisting of Formulas I to K below. [ka] [ka] [ka]

[0046] In formula I, j=4 to 80, k=1 to 10, and q=1 to 10. In formula J, r=4 to 80. In formula K, t=4 to 80.

[0047] In embodiments, the first siloxane monomer may be present in a range of 50% to 91% by weight and the second siloxane monomer may be present in a range of 9% to 50% by weight, based on the total weight of the first siloxane monomer and the second siloxane monomer. In embodiments, the first siloxane monomer may be present in a range of 60% to 91% by weight and the second siloxane monomer may be present in a range of 9% to 40% by weight, based on the total weight of the first siloxane monomer and the second siloxane monomer. In embodiments, the first siloxane monomer may be present in a range of 70% to 91% by weight and the second siloxane monomer may be present in a range of 9% to 30% by weight, based on the total weight of the first siloxane monomer and the second siloxane monomer.

[0048] The blue light blocking compound may be present in an amount ranging from about 0.01% by weight to about 5% by weight based on the total weight of the blue light blocking composition (the polymerizable monomers in the blue light blocking composition consist of a hydrophilic monomer, a first siloxane monomer, and a second siloxane monomer), but the present disclosure is not limited thereto. The content of the blue light blocking compound can be adjusted according to the required blue light blocking rate of the blue light blocking product.

[0049] In embodiments, the blue light blocking composition may further comprise an ultraviolet absorber and / or an initiator. The initiator may be a thermal initiator or a photoinitiator.

[0050] The ultraviolet absorber may be at least one selected from the group consisting of 2-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl]ethyl-2-methacrylate, 2-(4-benzyl-3-hydroxyphenoxy)ethyl acrylate, and N-(4-hydroxy-3(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)phenyl)methacrylamide. In embodiments, the ultraviolet absorber is 2-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl]ethyl-2-methacrylate.

[0051] The ultraviolet absorber may be present in a range of about 0.5% to about 2.5% by weight, based on the total weight of the blue light blocking composition.

[0052] The thermal initiator can be at least one selected from the group consisting of azobisisobutyronitrile, 2,2'-azo-bis-(2-methylbutyronitrile), and azobisisoheptanenitrile. In embodiments, the thermal initiator is azobisisobutyronitrile.

[0053] The photoinitiator can be at least one selected from the group consisting of bis(2,4,6-trimethylbenzyl)phenyl-phosphine oxide, benzoin diethyl ether, phenyl dimethyl ketal, α,α-diethoxyacetophenone, and 2-hydroxy-2-methyl-1-phenyl-1-propanone.

[0054] The initiator may be in the range of about 0.45% to about 0.75% by weight, based on the total weight of the blue light blocking composition.

[0055] The above components can be mixed in specific ratios to form a blue-light-blocking composition for manufacturing an ophthalmic device. In embodiments, the blue-light-blocking composition of the present disclosure can be placed in a contact lens mold, and the components in the blue-light-blocking composition undergo a curing reaction (thermal curing reaction or photocuring reaction) via heating or light irradiation to form the ophthalmic device. The heating temperature is about 30°C to about 150°C, and the heating time is about 1 to 12 hours. In embodiments, the reaction conditions can be heating at 30 to 70°C for 0 to 2 hours, heating at 70 to 100°C for 2 to 4 hours, or heating at 100 to 150°C for 4 to 12 hours. In embodiments, a hydration process and / or sterilization process can be carried out after the curing reaction. The hydration process can include immersing the ophthalmic device in alcohol and pure water, followed by placing the ophthalmic device in a buffer solution to allow it to equilibrate.

[0056] The blue light blocking compounds of the present disclosure are compatible with a variety of polymerization reactions in different formulations. In embodiments, the blue light blocking compounds of the present disclosure are compatible with a variety of polymerization reactions for producing ophthalmic devices, such as a variety of polymerization reactions for producing hydrogel contact lenses and a variety of polymerization reactions for producing silicone hydrogel contact lenses.

[0057] The present disclosure will be explained in more detail with reference to examples, but the present disclosure is not limited to these examples. [Example]

[0058] [Compatibility and reactivity evaluation] The blue light blocking compound of Example 1 has a structure represented by the above formula 1-1. The blue light blocking compound of Example 2 has a structure represented by the above formula 1-2. The blue light blocking compound of Example 3 has a structure represented by the above formula 1-3.

[0059] The blue light blocking compound of Comparative Example 1 has a structure represented by the following formula 8: [ka]

[0060] The blue light blocking compounds of Examples 1-3 and Comparative Example 1 were dissolved in 2-hydroxyethyl methacrylate (represented by HEMA in the tables, which is also a hydrophilic monomer used in the manufacture of ophthalmic devices) and a silicone hydrogel contact lens composition to observe miscibility, and the results are shown in Table 1 below. The higher the value in Table 1, the better the miscibility. The silicone hydrogel contact lens composition used for miscibility evaluation included polymerizable monomers, which included a hydrophilic monomer, a first siloxane monomer, and a second siloxane monomer.

[0061] [Table 1]

[0062] As shown in Table 1, the miscibility of the blue light-blocking compounds of Examples 1 to 3 with the materials of the ophthalmic device is significantly higher than that of the blue light-blocking compound of Comparative Example 1 with the materials of the ophthalmic device. Therefore, the miscibility of the blue light-blocking compounds with the materials of the ophthalmic device can be effectively improved by the blue light-blocking compounds of the present disclosure. High miscibility means good reactivity in the subsequent polymerization reaction, and therefore, the reactivity can be effectively improved by the blue light-blocking compounds of the present disclosure.

[0063] [Evaluation of blue light absorption rate] Examples 4 and 5: The blue light blocking compound of Example 1 is added to a silicone hydrogel contact lens composition at a rate of 0.1% and 1.0%, respectively, and the blue light blocking compound composition is used to manufacture an ophthalmic device by the method described above.

[0064] Examples 6 and 7: The blue light blocking compound of Example 2 is added to a silicone hydrogel contact lens composition at a rate of 0.1% and 1.0%, respectively, and the blue light blocking compound composition is used to manufacture an ophthalmic device by the method described above.

[0065] Examples 8 and 9: The blue light blocking compound of Example 3 is added to a silicone hydrogel contact lens composition at a rate of 0.1% and 1.0%, respectively, and the blue light blocking compound composition is used to manufacture an ophthalmic device by the method described above.

[0066] Comparative Examples 2 and 3: The blue light blocking compound of Comparative Example 1 was added to a silicone hydrogel contact lens composition at a rate of 0.1% and 1.0%, respectively, and the blue light blocking compound composition was used to manufacture an ophthalmic device by the above-mentioned method.

[0067] The ophthalmic devices of Examples 4 to 9 and Comparative Examples 2 and 3 were evaluated for blue light absorptivity. The results are shown in Table 2 below. Blue light absorptivity was measured by absorption spectroscopy using a UV-VIS spectrophotometer (Shimadzu UV-2600). Blue light absorptivity represents the amount of blue light with wavelengths between 380 nm and 460 nm absorbed by the silicone hydrogel contact lens.

[0068] [Table 2]

[0069] As shown in Table 2, in Comparative Example 3, an ophthalmic device could not be formed, and therefore the blue light absorbance could not be measured. The reason for the inability to form an ophthalmic device in Comparative Example 3 is that the blue light blocking compound of Comparative Example 1 was poorly miscible with the silicone hydrogel contact lens composition, resulting in precipitation when the blue light blocking compound was added at 1.0%. As shown in Table 2, the blue light absorbances of Examples 4, 6, and 8 were all higher than those of Comparative Example 2, indicating that the blue light blocking compound of the present disclosure has a blue light blocking effect. Furthermore, at the same addition amount, the blue light blocking effect of the blue light blocking compound of the present disclosure is higher than that of the blue light blocking compound of the comparative example. The blue light absorbances of Examples 4, 6, and 8 and Comparative Example 2 demonstrate that the blue light blocking compound of the present disclosure can achieve better blue light blocking effect at a lower addition amount, thereby reducing costs and improving the appearance of ophthalmic devices. In addition, the blue light absorbance of Example 5 is higher than that of Example 4, the blue light absorbance of Example 7 is higher than that of Example 6, and the blue light absorbance of Example 8 is higher than that of Example 6, which means that the blue light absorbance of the blue light blocking compound of the present disclosure increases as the loading amount increases. In addition, even if the loading amount increases, the blue light blocking compound still shows good miscibility.

[0070] Furthermore, the blue light-blocking compound of Example 1 can be added to a silicone hydrogel contact lens composition at a ratio of 1.5% and 2%, respectively. When the blue light-blocking compound composition is used to manufacture an ophthalmic device according to the above method and the ophthalmic device is subjected to the above-mentioned blue light absorbance evaluation, the blue light absorbance of the ophthalmic device is 56.1% and 65.3%, respectively, which means that the blue light absorbance of the blue light-blocking compound of the present disclosure increases with increasing addition amount. The addition amount of the blue light-blocking compound of the present disclosure can be much higher than the addition amount of the blue light-blocking compound of the comparative example to achieve a better blue light blocking effect (Table 2 shows that the blue light-blocking compound of Comparative Example 1 can only be used in an addition amount of less than 1.0%).

[0071] The blue light-blocking compounds of the present disclosure have good miscibility, allowing them to be uniformly dispersed in the materials of ophthalmic devices, eliminating or reducing the use of chemicals that help to uniformly disperse the blue light-blocking compounds. Therefore, the present disclosure can reduce the use of chemicals, simplify the manufacturing process, and reduce the risk of chemical residues in the final products (such as blue light-blocking ophthalmic devices, blue light-blocking coatings, and blue light-blocking films). In addition, high miscibility means good reactivity in the subsequent polymerization reaction, resulting in higher quality ophthalmic devices.

[0072] While the present disclosure has been described by way of example and in terms of exemplary embodiment(s), it is to be understood that the present disclosure is not limited thereto. To the contrary, the present disclosure is intended to cover various modifications and similar arrangements and procedures, and the scope of the appended claims, therefore, should be accorded the broadest interpretation so as to encompass all such modifications and similar arrangements and procedures.

Claims

1. A blue light blocking compound represented by the following formula 1: 【Chemistry 1】 In Formula 1, R 1 and R 8 are each independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a halogen, N(R 1a ) 2 , OR 1b , S.R. 1c , S.O. 2 R 1d , C.O.R. 1e , NO 2 , CN, SOR 1h , a 5-membered heterocycle, a 6-membered heterocycle, or R 1 and R 8 and R 1a and R 1b are each independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted phenyl group; R 1d is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or OH; R 1e is H, OH, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or —O—R 1f and R 1c , R 1f , and R 1h are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted alkenyl group; R 2 is H or substituted or unsubstituted C 1 ~C 4 is an alkyl group, R 3 is X-(C n H 2n O m ) p and X is O, NH, S, or SO 2 wherein m is 1 to 4, n is 1 to 4, and p is 1 to 4; R 4 is CN or C(O)R 6 and R 6 is H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, R 3 —C(O)—CCH 2 R 5 , or O-R 1g and R 1g is a substituted or unsubstituted C 1 ~C 4 an alkyl group, or a substituted or unsubstituted C 1 ~C 4 is an alkenyl group, R 5 is H or substituted or unsubstituted C 1 ~C 4 A blue light blocking compound that is an alkyl group.

2. 2. The blue light blocking compound of claim 1, wherein X is O or NH, m is 1 to 3, n is 1 to 3, and p is 1 to 3.

3. 2. The blue light blocking compound of claim 1, wherein X is O or NH, m is 1 to 2, n is 1 to 2, and p is 1 to 2.

4. A blue light blocking composition, comprising: a blue light blocking compound represented by the following formula 1: a polymerizable monomer, 【Chemistry 2】 In Formula 1, R 1 and R 8 are each independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a halogen, N(R 1a ) 2 , OR 1b , S.R. 1c , S.O. 2 R 1d , C.O.R. 1e , NO 2 , CN, SOR 1h , a 5-membered heterocycle, a 6-membered heterocycle, or R 1 and R 8 and R 1a and R 1b are each independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted phenyl group; R 1d is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or OH; R 1e is H, OH, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or —O—R 1f and R 1c , R 1f , and R 1h are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted alkenyl group; R 2 is H or substituted or unsubstituted C 1 ~C 4 is an alkyl group, R 3 is X-(C n H 2n O m ) p and X is O, NH, S, or SO 2 wherein m is 1 to 4, n is 1 to 4, and p is 1 to 4; R 4 is CN or C(O)R 6 and R 6 is H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, R 3 —C(O)—CCH 2 R 5 , or O-R 1g and R 1g is a substituted or unsubstituted C 1 ~C 4 an alkyl group, or a substituted or unsubstituted C 1 ~C 4 is an alkenyl group, R 5 is H or substituted or unsubstituted C 1 ~C 4 The blue light blocking composition is an alkyl group.

5. 5. The blue light blocking composition of claim 4, wherein the polymerizable monomer comprises a hydrophilic monomer selected from the group consisting of 2-hydroxyethyl methacrylate (HEMA), methyl methacrylate (MMA), methacrylic acid (MAA), N-vinylpyrrolidone (NVP), N,N-dimethylacrylamide (DMA), 4-acryloylmorpholine (AcMO), 2-hydroxyethyl acrylamide (HEAA), glycidyl methacrylate (GMA), glycerol monomethacrylate (GMMA), acrylic acid (AA), N,N-di(methylmethacrylamide) (DMA), hexafluoroisopropyl methacrylate (HFMA), N-vinyl-N-methylacetamide, glycine vinyl carbonate, 2-methacryloyloxyethyl phosphorylcholine, and 2-hydroxybutyl methacrylate.

6. The blue light blocking composition of claim 4 , wherein the polymerizable monomer comprises at least one siloxane monomer.

7. 5. The blue light blocking composition of claim 4, further comprising a thermal initiator or a photoinitiator.

8. 10. Use of the blue light blocking compound of claim 1 in the manufacture of an ophthalmic device.

9. 1. Use of a blue light blocking composition in the manufacture of an optical film, a screen protector, a display, or an ophthalmic device, the blue light blocking composition comprising: a blue light blocking compound represented by the following formula 1: a polymerizable monomer, 【Transformation 3】 In Formula 1, R 1 and R 8 are each independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a halogen, N(R 1a ) 2 , OR 1b , S.R. 1c , S.O. 2 R 1d , C.O.R. 1e , NO 2 , CN, SOR 1h , a 5-membered heterocycle, a 6-membered heterocycle, or R 1 and R 8 and R 1a and R 1b are each independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted phenyl group; R 1d is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or OH; R 1e is H, OH, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or —O—R 1f and R 1c , R 1f , and R 1h are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted alkenyl group; R 2 is H or substituted or unsubstituted C 1 ~C 4 is an alkyl group, R 3 is X-(C n H 2n O m ) p and X is O, NH, S, or SO 2 wherein m is 1 to 4, n is 1 to 4, and p is 1 to 4; R 4 is CN or C(O)R 6 and R 6 is H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, R 3 —C(O)—CCH 2 R 5 , or O-R 1g and R 1g is a substituted or unsubstituted C 1 ~C 4 an alkyl group, or a substituted or unsubstituted C 1 ~C 4 is an alkenyl group, R 5 is H or substituted or unsubstituted C 1 ~C 4 Use an alkyl group.

10. 10. A method for preparing the blue light blocking compound of claim 1, said method comprising: providing a compound represented by formula 2: hydrolyzing the compound to obtain an intermediate product; and esterifying the intermediate product to obtain the blue light blocking compound of claim 1. 【Chemistry 4】 In Equation 2, R 1 and R 8 are each independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a halogen, N(R 1a ) 2 , OR 1b , S.R. 1c , S.O. 2 R 1d , C.O.R. 1e , NO 2 , CN, SOR 1h , a 5-membered heterocycle, a 6-membered heterocycle, or R 1 and R 8 and R 1a and R 1b are each independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted phenyl group; R 1d is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or OH; R 1e is H, OH, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or —O—R 1f and R 1c , R 1f , and R 1h are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted alkenyl group; R 2 is H or substituted or unsubstituted C 1 ~C 4 is an alkyl group, R 4 ' is CN or C(O)R 6 ' and R 6 is H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or O—R 1j and R 1j is a substituted or unsubstituted C 1 ~C 4 an alkyl group, or a substituted or unsubstituted C 1 ~C 4 The method according to claim 1, wherein the alkenyl group is an alkenyl group.

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