Eye lenses containing acrylonitrile compounds

Abstract

The present invention relates to an ophthalmic lens containing a compound of formula (I), a method for preparing the same, and the use of a compound of formula (I) in an ophthalmic lens for absorbing blue light.

Description

[Technical Field]

[0001] This disclosure relates to an ophthalmic lens containing an acrylonitrile compound, a method for manufacturing the lens, and the use of the compound in an ophthalmic lens for absorbing blue light. [Background technology]

[0002] Light that reaches and enters the human eye is divided into visible light, which includes wavelengths of approximately 380-780 nm, and invisible light, which includes light in the ultraviolet range (UV-A and UV-B light of approximately 280-380 nm) and the infrared range (near-IR light of approximately 780-1400 nm).

[0003] UV light is known to be harmful to the human eye. In particular, it may accelerate ocular aging, which can lead to premature cataracts or more severe damage such as photokeratitis or "snow blindness."

[0004] Blue light, also known as high-energy visible (HEV) light, corresponds to visible light in the blue-violet band between 380 and 500 nm. Prolonged exposure to blue light emitted from digital devices such as televisions, laptops, tablets, and smartphones, as well as from fluorescent and LED lighting, is harmful because blue light can reach the retina. Several specific ranges of blue light have been shown to cause photokeratitis; digital eye strain, or computer vision syndrome, including blurred vision, difficulty focusing, dry eyes and eye irritation, headaches, neck and back pain; disruption of circadian rhythms; decreased melanin production; age-related macular degeneration; glaucoma; retinal degenerative diseases; breast and prostate cancer; diabetes; heart disease; obesity and depression.

[0005] Blue light in the range of approximately 420-450 nm is considered particularly harmful. Damage from UV light and blue light can be prevented by incorporating light-absorbing additives into eye lenses.

[0006] Three different methods can be used to prepare light-absorbing ophthalmic lenses.

[0007] The first method involves impregnating the polymerized lens in a bath containing a light-absorbing additive. However, this method adds an extra step to the lens manufacturing process, which is undesirable from the standpoint of cost and time.

[0008] The second method involves coating the surface of the ophthalmic lens with a light-absorbing substance. However, incorporating a high amount of light-absorbing additives into the coating weakens its mechanical properties.

[0009] A third method involves incorporating light-absorbing additives into the bulk liquid formulation (i.e., before polymerization). However, incorporating high amounts of light-absorbing additives into the bulk can lead to undesirable yellowing, as well as compatibility issues and reduced mechanical properties.

[0010] Currently, the best commercially available compounds for use in lenses are benzotriazoles and benzophenones. The main problem with commercially available compounds is that their spectral characteristics are not well suited for blue-light filtering applications: typically, their maximum absorption wavelength (λ) max This stems from the fact that the maximum absorption wavelength (λ) is lower than what would be needed to achieve significant light reduction within the blue light cut range. In fact, most products available on the market have a maximum absorption wavelength (λ) below 350 nm. max ) shows, leading to very insufficient absorption or no absorption at wavelengths above 400 nm. Other compounds show maximum absorption wavelengths within the blue cut range, but at these wavelengths they have low absorption extinction coefficients, i.e., 30,000 M -1 cm -1 It has an absorption extinction coefficient of less than .

[0011] Such a discrepancy between the spectral characteristics at the blue cut and the application leads to two consequences. - When blue-cutting molecules are introduced in a volume with narrow dimensions, such as a film or coating, the concentration required to achieve blue-cutting would make it impractical or unfeasible. - When blue-cutting molecules are introduced in bulk, the concentration required to achieve blue-cutting may lead to compatibility issues such as blooming (where additives migrate from the lens during polymerization, causing surface defects) or a decrease in the thermomechanical properties of the matrix. [Overview of the project] [Problems that the invention aims to solve]

[0012] Therefore, blue-cutting molecules that are efficient at low concentrations are needed to limit the degradation of the polymer matrix's mechanical properties and compatibility issues.

[0013] In particular, there is a need for robust lenses whose optical properties remain stable over time.

[0014] The applicant has found that this need can be met by an ophthalmic lens containing a compound of formula (I) as defined herein as a light-absorbing additive. In fact, the compound of formula (I) may have maximum wavelength absorption in the range of 350-400 nm, and at these wavelengths, a high absorption extinction coefficient, i.e., 30,000 M -1 cm -1 It may possess the above properties and therefore can be used to absorb blue light more efficiently than existing commercially available lenses containing, for example, benzotriazoles and benzophenones.

[0015] Ophthalmic lenses containing the compound of formula (I) offer better protection against BVC B' or UV rays than commercially available lenses containing the same amount of conventional benzotriazole. cut It exhibits higher blue light reduction performance, as represented by [the formula]; and furthermore, it shows low undesirable yellowing and good transparency.

[0016] The compound of formula (I) is more efficient for blue light cutting applications, thus reducing the amount of light absorber that needs to be introduced into the lens. As a result, migration of the light absorber on the lens surface during polymerization is minimized, leading to lower contamination of the mold surface and ultimately eliminating the need to clean the mold between successive uses. The reduced amount of blue cutting molecules used can lower the cost of lens manufacturing.

[0017] In addition, since the mechanical properties of a substrate are usually improved when additives and / or auxiliaries are used in lower amounts, a substrate containing a low amount of the compound of formula (I) will show improved thermomechanical properties.

[0018] The lens according to the present invention exhibits even higher light resistance and maintains its optical properties over time.

[0019] Furthermore, the compound of formula (I) can also be used in narrow-dimensional applications such as light filtering coatings, hard coats, films, and laminates.

[0020] In addition, the compound of formula (I) can be encapsulated in nanoparticles, which can lead to a reduction in yellowing in the allyl matrix, which requires a high amount of catalyst to initiate polymerization.

[0021] Finally, molecules that are effective in allowing a limited range of visible light to pass through, either to protect the wearer from harmful light or to improve the wearer's vision, are also needed, particularly to improve color perception, contrast, or color discrimination (for colorblind wearers).

[0022] The inventors have found that the combination of optical properties of the ophthalmic lenses according to the present invention makes them particularly useful in optical applications. [Means for solving the problem]

[0023] The first object of the present invention is, - Plastic base, - Compound of formula (I), or a salt thereof It is an ophthalmic lens that includes [ka] X, R1, R2, R3, R4, and R5 are as defined herein.

[0024] A second object of the present invention is a) A step of providing a monomer or oligomer that can prepare a plastic base, b) A step of mixing a monomer or oligomer with a compound of formula (I) as defined herein and a catalyst suitable for polymerization of monomers and oligomers to form a polymerizable liquid composition, c) A step of curing a polymerizable liquid composition The present invention relates to a process for preparing ophthalmic lenses, which includes the following:

[0025] A third object of the present invention is the use of a compound of formula (I) as defined herein in an ophthalmic lens for absorbing blue light.

[0026] A fourth object of the present invention is a composition comprising a plastic base and a compound of formula (IA), [ka] R1, R2, R3, R4, and R5 are as defined herein.

[0027] A fifth object of the present invention is the use of compositions as defined herein in optical articles.

[0028] The sixth object of the present invention is [ka] Alternatively, the present invention provides novel compounds selected from their salts.

[0029] Eye lenses This invention relates to ophthalmic lenses.

[0030] As used herein, the term "ophthalmic lens" refers to any type of lens intended to be supported by the wearer's face, which may be for the purpose of improving or enhancing vision, protecting from the environment, for fashion, or for ornamentation. The term may refer to non-corrective lenses (also called plano lenses), semi-finished lens blanks, and corrective lenses, such as progressive multifocal lenses, single-focus or multifocal lenses, etc. Further examples of ophthalmic lenses include electronic lenses, virtual reality (VR) lenses, augmented reality lenses (AR), and the like.

[0031] The ophthalmic lens of the present invention contains a compound of formula (I) or a salt thereof,

Chemical formula

Chemical formula

[0032] Expression “(C1~C 12 "Alkyl" refers to a linear or branched alkyl group containing 1 to 12 carbon atoms. 12 )Alkyl groups refer to methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, or dodecyl. Branched (C1~C 12 )An alkyl group means an alkyl group as defined above, which includes a substituent selected from the list of linear alkyl groups defined above, and the linear alkyl group is also branchable. Examples of branched alkyl groups include a tert-butyl group, a sec-butyl group, and an isopropyl group. (C1~C 12 The alkyl group is particularly a (C1-C6) alkyl group, more particularly a (C1-C3) alkyl group, and is preferably methyl or ethyl.

[0033] R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 and R 14 In particular, independently, (C1~C 12 ) Selected independently of alkyl.

[0034] -CO2R6 is particularly a methyl ester or ethyl ester. -OR7 is specifically methoxy or ethoxy. -SR8 is specifically -SCH3. -SOR9 is specifically -SOCH3. -SO2R 10 This is particularly -SO2CH3. -NHR 11 These are, in particular, NHCH3 or NHCH2CH3. -N(R 12 )2 is specifically N(CH3)2 or N(CH2CH3)2. -NHCOR 13 In particular, it is -NHCO(CH3). -NHSO2OR 14 In particular, it is NHSO2OCH3. -NR 15 In particular, -NR 15 The option is selected from -NCH3 and -NCH3CH3.

[0035] R 6a , R 7a , R 8a , R 9a , R 10a , R 11a R 12a , R 13a and R 14a In particular, (C1~C 12 ) Selected independently of alkyl.

[0036] -CO2R 6a These are particularly methyl esters or ethyl esters. -OR 7a These are particularly methoxy or ethoxy compounds. -SR 8a This is particularly -SCH3. -SOR 9a This is particularly -SOCH3. -SO2R 10a This is particularly -SO2CH3. -NHR 11a These are, in particular, NHCH3 or NHCH2CH3. -N(R 12a )2 is specifically N(CH3)2 or N(CH2CH3)2. -NHCOR13a In particular, it is -NHCO(CH3). -NHSO2 or 14a In particular, it is NHSO2OCH3.

[0037] The term “(C1~C 12 )Haloalkyl is a halogen atom substituted with one or more halogen atoms, particularly selected from F or Cl, as defined above (C1~C 12 ) refers to alkyl groups. -CF3 is (C1~C 12 ) This is a specific example of a haloalkyl.

[0038] The term “(C1~C 12 )alkoxy is (C1~C 12 ) refers to alkyl-O, where (C1~C 12 )Alkyl is as defined above. "(C1~C 12 Examples of alkoxys are methoxy and ethoxy.

[0039] The term “(C2~C 12 An "alkenyl" is an alkenyl containing one or more carbon-carbon double bonds, as defined above (C1~C 12 This refers to alkyl groups. Examples of alkenyls include ethenyl and allyl groups.

[0040] The term “(C2~C 12 )Alkynnyl is a compound containing one or more carbon-carbon triple bonds, as defined above (C1~C 12 This refers to an alkyl group. Examples of alkynyl groups include ethynyl or propargyl.

[0041] The term “(C1~C 12 A heteroalkyl group is a group that further contains heteroatoms in its chain, particularly selected from O, NH, or S, as defined above (C1-C 12 This refers to alkyl groups. An example is the ethylene glycol group (HO-CH2-CH2-O-).

[0042] The term “(C3~C12 A "cycloalkyl" refers to a saturated cyclic carbon ring containing 3 to 12 carbon atoms. In particular, cycloalkyls are (C3-C6) cycloalkyls. Examples include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0043] The term “(C3~C 12 A "heterocycloalkyl" refers to a cycloalkyl group, as defined above, that further contains a heteroatom, particularly selected from O or N, within its ring. An example is the tetrahydropyranyl ring.

[0044] The term “(C6~C 18 The term "aryl" refers to an aromatic group consisting of 6 to 18 carbon atoms within its ring. (C6~C 18 )The aryl group is particularly (C6~C 12 It is an aryl group. Aryls are particularly phenyl.

[0045] (C6~C 18 )Aaryl-(C1~C 12 )alkyl" is defined as (C6~C) as above. 18 )An aryl group is bonded to it, as defined above (C1~C 12 ) Refers to alkyl groups. (C6~C 18 )Aaryl-(C1~C 12 ) Alkyl alkyl groups are particularly benzyl.

[0046] The term "heteroaryl" refers to any monovalent group of a monocyclic or polycyclic 5-10 membered aromatic group (such as a bicyclic group) containing 1-3 heteroatoms independently selected from oxygen, nitrogen, and sulfur. Heteroaryls can optionally be substituted with one or more substituents on the carbon atom or heteroatom, the substituents as defined above for "aryl". Heteroaryls include pyridyl, furanyl, imidazolyl, and pyrrolyl.

[0047] (5-10 member) heteroaryl-(C1-C12 )alkyl is a group to which a heteroaryl group as defined above is bonded, as defined above (C1~C 12 ) refers to alkyl groups.

[0048] The aryl or heteroaryl groups defined above may optionally be substituted with one or more substituents, particularly one or two substituents, wherein the substituents are, in particular, • Halogens, especially F or Cl, • Carboxylic acid esters, especially methyl esters or ethyl esters, (C1~C 12 ) Alkyl, especially methyl, ethyl or isopropyl, (C1~C 12 ) Alkoxy, especially methoxy or ethoxy, • Carboxylic acid, Nitrile, • Amines, especially -NH2, NHCH3, or N(CH3)2 Selected from.

[0049] In certain embodiments, the aryl or heteroaryl group is not substituted.

[0050] According to a particular embodiment, the ophthalmic lens according to the present invention comprises a compound of formula (I), the compound of formula (I) not in the form of a salt.

[0051] According to a particular embodiment, the ophthalmic lens according to the present invention comprises a compound of formula (I) in the form of a salt. This is characterized in particular by the compound of formula (I) comprising at least one basic nitrogen atom capable of forming the salt, where X is N or NR 15 This could be the case. Alternatively, if the compound of formula (I) contains a carboxylic acid group, the salt of formula (I) may be a carboxylic acid salt having a sodium, potassium, or lithium counterion in particular.

[0052] In particular, salts useful in relation to the present invention are hydrochloride salts or sulfate salts.

[0053] According to a particular embodiment, R1 and R 1a This is selected independently of -CN or -CO2Et.

[0054] According to a particular embodiment, R2, R 2a , R3, R 3a , R4, R 4a , R5 and R 5a is H or (C1~C 12 ) Selected from alkyl, preferably H or CH3.

[0055] According to a particular embodiment, R2 and R 2a H is H.

[0056] According to a particular embodiment, R4 and R 4a H is H.

[0057] According to a particular embodiment, R3, R 3a , R5 and / or R 5a This is CH3.

[0058] According to a particular embodiment, R 16 This is selected from halogen atoms, and in particular from F or Cl.

[0059] According to a particular embodiment, R 16 (C1~C 12 ) Selected from alkoxys, and in particular selected from methoxy or ethoxy.

[0060] According to a particular embodiment, R 16 (C6~C 18 ) Selected from aryls, especially phenyls.

[0061] According to a particular embodiment, X is NH or NR 15 And, R 15 In particular, -(C1~C 12 )alkyl (the alkyl has 1 to 3 R 16 (It is optionally substituted by the base) The aforementioned R 16 In particular, it is selected from F, methoxy, or phenyl. More specifically, -NR 15 This is selected from -NCH3, -NCH3CH3-N-CH2C(CH2CH3)(CH2)3CH3, -NC(CH3)3, -NCH2-CF3, N(CH2)2-phenyl, N-(CH2)4-F, or N-(CH2)4-OCH3. More specifically, X is NH or NCH3.

[0062] According to a particular embodiment, the compound of formula (I) is R1 is -CN, and X is -NR 15 And, R 15 However, as defined in claim 1, and especially halogen atoms, (C1~C 12 )alkoxy, (C6~C 18 ) Select 1 to 3 R from the aryl 16 -(C1~C) which are arbitrarily substituted by the base. 12 ) Particularly selected from alkyl groups, or R 1a is -CN, R 2a , R 3a , R 4a and R 5a A compound of formula a as defined in claim 1, wherein H is present. That is the case.

[0063] According to a particular embodiment, the compound of formula (I) is R1 is -CN, R2, R3, R4, and R5 are H. X is -NR 15 And, R 15 However, as defined above, especially halogen atoms, (C1~C 12 )alkoxy, (C6~C 18 ) Select 1 to 3 R from the aryl 16 -(C1~C) which are arbitrarily substituted by the base. 12 ) Particularly selected from alkyl groups, or R 1a is -CN, R 2a , R 3a , R 4a and R 5a Compounds of formula a as defined above, where H is That is the case.

[0064] Surprisingly, the inventors have found that X is NR 15 In this case, we have found that the ophthalmic lenses disclosed herein are particularly stable during long-term storage. In particular, such lenses retain sufficient optical properties when stored for more than one year.

[0065] According to a particular embodiment, R 1a is equal to R1, and R 2a is equal to R², and R 3a is equal to R3, and R 4a This is equal to R4.

[0066] According to a particular embodiment, the compound of formula (I) is such that R2 is (C6~C 18 In the case of an aryl or (5-10) member heteroaryl, R1 is -CONH2 or -CO2R6 (where R6 is as defined above).

[0067] In a particular embodiment of formula (I), R2 is H, F, Cl, Br, I, -OH, -OR7, -SH, -SR8, -SOR9, SO2R 10 -NH2, -NHR 11 , -N(R 12 )2, -NHCOR 13 ,-NHSO2OR 14 -NO2, -CN, (C1~C 12 ) Alkyl, (C1~C 12 ) Haloalkyl, (C2~C 12 ) Alkenil, (C2~C 12 ) Alkinyl, (C1~C 12 ) Heteroalkyl, (C3~C 12 )Cycloalkyl, (C3~C 12 ) Heterocycloalkyl, (C6~C 18)Aaryl-(C1~C 12 )alkyl, or (5-10 member) heteroaryl-(C1-C 12 ) Selected from alkyl groups.

[0068] In certain embodiments, L is selected from propylene or butylene, particularly propylene.

[0069] According to certain embodiments, the compound of formula (I) is a compound of formulas (II), (III), (IV), and (V), particularly formula (II): [ka] It has the structure of [the object].

[0070] When R1 is -CN, compounds (II) and (III) are structurally identical. When R1 is -CO2R6 or -CO2NH2, compounds (II) and (III) differ with respect to the stereochemistry of the double bond, and they can be in a Z configuration or an E configuration. In compound (I), the stereochemistry may be such that a mixture of E and Z double bonds is present.

[0071] According to a particular embodiment, R 6 (C2~C 12 )When X is an alkenyl, X is S, NH, or -NR as defined above. 15 That is the case.

[0072] In one embodiment, R 1 , R 1a , R 2 , R 2a , R 3 , R 3a , R 4 , R 4a , R 5 , R 5a , R 6a and R 6 (C2~C 12 ) Not Alkenil.

[0073] According to a particular embodiment, the compound of formula (I) is (I-1), (I-2), (I-3), (I-4), (I-5), (I-6), or (I-7):: [ka] Selected from.

[0074] In particular, the compound of formula (I) is included in ophthalmic lenses as such, meaning that the compound of formula (I) is not covalently bonded to the plastic base.

[0075] The compound of formula (I) contained in the ophthalmic lens of the present invention may show significant absorption in the range of blue light. In particular, the compound of formula (I) shows a maximum absorption wavelength (λ) of 400 nm or less. max ) may have. More specifically, the compound of formula (I) may have a maximum absorption wavelength in the range of 350-400 nm, particularly 360-400 nm, particularly 370-400 nm, and more particularly 370-395 nm.

[0076] Maximum absorption wavelengths exceeding these ranges may lead to an undesirablely high yellowness index in lenses containing the compound of formula (I). Maximum absorption wavelengths below these ranges may lead to insufficient absorption in the blue light range.

[0077] Maximum absorption wavelength (λ max In ), the compound of formula (I) is 30,000M -1 cm -1 It may have the above molar absorption extinction coefficient (ε).

[0078] More specifically, the compound of formula (I) is 30,000 to 80,000 M -1 cm -1 The range, especially 30,000 to 70,000 million -1 cm -1 The range, and even more specifically 30,000-45,000M -1 cm -1 It may have a molar absorption extinction coefficient (ε) within the range of .

[0079] λ of the compound of formula (I) max And ε can be measured with respect to a 20 ppm solution of the compound of formula (I) in an organic solvent such as ethanol, acetonitrile, or tetrahydrofuran, particularly in tetrahydrofuran.

[0080] The "molar absorption extinction coefficient" is a measure of how strongly a chemical species absorbs and attenuates light at a given wavelength. It is an intrinsic property of the chemical species. It is defined as the ratio of absorption to the length of the optical path moved by electromagnetic radiation in a given solution. This is M -1 m -1 It is expressed as follows: It does not depend on the concentration of the solution or the thickness of the light passing through it; on the other hand, it depends on the wavelength of the incident light as well as the properties of the solute and solvent.

[0081] The compound of formula (I) is represented by the following scheme: [ka] It can be obtained by Knoevenagel condensation according to the following formula.

[0082] After the reaction is complete, the crude product can be purified by known techniques such as crystallization or column chromatography.

[0083] The ophthalmic lens of the present invention further comprises a plastic base.

[0084] As used herein, the term “plastic base” refers to a bare ophthalmic substrate, such as an unfinished, untreated, or uncoated ophthalmic lens.

[0085] Preferably, the plastic base of the ophthalmic lens of the present invention is transparent.

[0086] As used herein, the term “transparent” is intended to mean a material having a transmittance greater than 85%, preferably 90% or more.

[0087] The refractive index of plastic bases can range from approximately 1.4 to 1.9, for example, approximately 1.5 to 1.9, approximately 1.6 to 1.9, approximately 1.7 to 1.9, approximately 1.8 to 1.9, approximately 1.4 to 1.8, approximately 1.4 to 1.7, approximately 1.4 to 1.6, approximately 1.45 to 1.85, approximately 1.45 to 1.75, or approximately 1.5 to 1.7, particularly in the range of 1.49 to 1.74.

[0088] The plastic base of the ophthalmic lens of the present invention may be any conventional optical substrate known in the art. In particular, the plastic base may be selected from thermosetting resins or thermoplastic resins, especially thermosetting resins. The resin may be selected from resins such as polyamide, polyimide, polysulfone, polycarbonate, polyethylene terephthalate, poly(methyl(meth)acrylate), cellulose triacetate or copolymers thereof, or from thermosetting resins such as cyclic olefin copolymers, allyl ester homopolymers or copolymers, allyl carbonate homopolymers or copolymers of linear or branched aliphatic or aromatic polyols, (meth)acrylic acid and its ester homopolymers or copolymers, thio(meth)acrylic acid and its ester homopolymers or copolymers, urethane and thiourethane homopolymers or copolymers, epoxy homopolymers or copolymers, sulfide homopolymers or copolymers, disulfide homopolymers or copolymers, episulfide homopolymers or copolymers, polythiol and polyisocyanate copolymers, and combinations thereof.

[0089] In one embodiment, the plastic base may include a copolymer of at least one polythiol and a polyisocyanate, preferably a copolymer of xylylene diisocyanate and 1,2-bis-[(2-mercaptoethyl)thio]-3-mercaptopropane, or a copolymer of bis(isocyanatomethyl)bicyclo[2.2.1]heptane and pentaerythritol tetrakis(3-mercaptopropionate) and 1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane, or a copolymer of xylylene diisocyanate and 4,8 (or 4,7 or 5,7)-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane.

[0090] In another embodiment, the plastic base may be a copolymer of an allyl monomer or allyl oligomer, such as diethylene glycol bis(allyl carbonate), ethylene glycol bis(allyl carbonate), diethylene glycol bis(allyl carbonate) oligomer, ethylene glycol bis(allyl carbonate) oligomer, bisphenol A bis(allyl carbonate), or diallyl phthalate, and a second monomer or oligomer that can polymerize with the allyl monomer or oligomer, such as an aromatic vinyl compound alkyl mono(meth)acrylate, di(meth)acrylate, tri(meth)acrylate, or tetra(meth)acrylate.

[0091] In the ophthalmic lens of the present invention, the compound of formula (I) may be contained in a plastic base or in a separate layer coated on the surface of the plastic base.

[0092] As used herein, a separate layer coated on the surface of a plastic base is defined as (i) a coating that is placed on a substrate, (ii) a coating that is not necessarily in contact with the substrate, i.e., one or more intermediate layers may be placed between the substrate and the layer in question, and (iii) a coating that does not necessarily completely cover the substrate.

[0093] A separate layer coated on a plastic-based surface can be manufactured from any material conventionally used for coating ophthalmic lenses. For example, the separate layer may be obtained by polymerization of a (meth)acrylic-based coating, a sol-gel-based coating, an epoxy-based coating, or a polyurethane-based coating.

[0094] Preferably, the compound of formula (I) is contained in the plastic base of the ophthalmic lens. The compound of formula (I) may be contained in the plastic base by dispersion of the compound of formula (I) in the raw materials (monomers) before polymerization. As a result, the compound of formula (I) may be uniformly dispersed in the plastic base of the ophthalmic lens. Alternatively, the compound of formula (I) may be contained in the plastic base by absorption. The absorption method may involve immersing the plastic base in a bath containing the compound of formula (I) for a predetermined time so that the compound of formula (I) can diffuse into the plastic base. As a result, the compound of formula (I) may be dispersed in a thin layer on the surface of the plastic base. In the absorption method, the thickness of the plastic base containing the compound of formula (I) does not depend on the overall geometry of the ophthalmic lens.

[0095] When the compound of formula (I) is contained in the plastic base, the amount of the compound of formula (I) may be in the range of 0.001 to 2% by weight, particularly 0.001 to 1% by weight, more particularly 0.001 to 0.1% by weight, even more particularly 0.01 to 0.05% by weight, or 0.003 to 0.035% by weight, based on the weight of the plastic base.

[0096] If the compound of formula (I) is contained in a separate layer coated on the surface of a plastic base, the amount of the compound of formula (I) may be in the range of 0.001 to 2% by weight, particularly 0.001 to 1% by weight, more particularly 0.001 to 0.1% by weight, and even more particularly 0.01 to 0.05% or 0.003 to 0.035% by weight, based on the weight of the separate total.

[0097] Furthermore, the compound of formula (I) can be encapsulated within nanoparticles. The nanoparticles may be dispersed within the plastic base of the ophthalmic lens or may be dispersed within a separate layer coated on the surface of the plastic base. Preferably, the nanoparticles are dispersed within the plastic base of the ophthalmic lens, and the plastic base comprises a copolymer comprising an allyl monomer or allyl oligomer as defined above.

[0098] [[ID=⑤]]The amount of the compound of formula (I) in the nanoparticles can be included in the range of 0.0001 to 90% by weight, particularly in the range of 0.01 to 50% by weight, and more particularly in the range of 0.1 to 10% by weight, based on the weight of the nanoparticles. [[ID=⑥]] [[ID=⑦]]

[0099] [[ID=⑧]] [[ID=⑨]]In the context of the present invention, the term "nanoparticles" is intended to mean individualized particles of any shape having a size in the range of 1 nm to 10 μm, preferably in the range of 10 nm to 5 μm, measured in its longest direction, as measured by Dynamic Light Scattering. [[ID=⑩]] [[ID=⑪]]

[0100] [[ID=⑫]] [[ID=⑬]]The nanoparticles can be polymer-based, i.e., they can contain a polymer, or they can be mineral-based, i.e., they can contain a metal oxide. [[ID=⑭]] [[ID=⑮]]

[0101] [[ID=⑯]] [[ID=⑰]]In a preferred embodiment, the polymer or metal oxide contained in the nanoparticles is a transparent material. [[ID=⑱]] [[ID=⑲]]

[0102] [[ID=⑳]] [[ID=㉑]]The ophthalmic lens may further contain a UV absorber other than the compound of formula (I). In one embodiment, the ophthalmic lens may further contain a benzotriazole UV absorber or a mixture thereof, preferably a benzotriazole UV absorber selected from 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chloro-2H-benzotriazole, and mixtures thereof. [[ID=㉒]] [[ID=㉓]]

[0103] [[ID=㉔]] It should be noted that in the above translation, the number "⑤" in the translation of ID=5 is a mistake in the original text you provided. It should be "" and has been directly translated as "" in the English translation. Please check and correct the relevant content in the original text if necessary.The benzotriazole UV absorber may be included in the plastic base or may be included in a separate layer coated on the surface of the plastic base.

[0104] Preferably, when the compound of formula (I) is included in the plastic base, the benzotriazole UV absorber is included in the plastic base, or when the compound of formula (I) is included in a separate layer coated on the surface of the plastic base, the benzotriazole UV absorber is included in the separate layer.

[0105] Advantageously, the amount of the benzotriazole UV absorber is lower than the amount generally required to absorb blue light when the compound of formula (I) is not present in the ophthalmic lens. When the benzotriazole UV absorber is included in the plastic base, the total amount of the benzotriazole UV absorber may be in the range of 0.001 to 2% by weight, particularly in the range of 0.01 to 1.5% by weight, more particularly in the range of 0.1 to 1.25% by weight, based on the weight of the plastic base. When the benzotriazole UV absorber is included in a separate layer coated on the surface of the plastic base, the total amount of the benzotriazole UV absorber may be in the range of 0.001 to 2% by weight, particularly in the range of 0.01 to 1.5%, more particularly in the range of 0.1 to 1.25% by weight, based on the weight of the separate layer.

[0106] The ophthalmic lens may further contain additives, in particular light stabilizers or anti-yellowing agents. As used herein, “light stabilizer” is intended to mean an additive that improves the light stability of the ophthalmic lens, in particular an additive that limits the degradation of the ophthalmic lens properties upon exposure to light, such as ultraviolet light. As used herein, “anti-yellowing agent” is intended to mean an additive that limits the yellowing of the ophthalmic lens. Particularly preferred light stabilizers are sulfide anti-yellowing additives, such as dialkylthiodipropionates or dialkylthiodiglycolates, and hindered amine light stabilizers (HALS), such as Tinuvin® 144, Tinuvin® 1130, Tinuvin® 479, Tinuvin® 123, or Hostavin® 3058, or mixtures thereof.

[0107] The light stabilizer may be contained within the plastic base or in a separate layer coated on the surface of the plastic base.

[0108] Preferably, if the compound of formula (I) is contained in the plastic base, the light stabilizer is contained in the plastic base, or if the compound of formula (I) is contained in a separate layer coated on the surface of the plastic base, the light stabilizer is contained in a separate layer.

[0109] Advantageously, the amount of light stabilizer is in the range of 0.001 to 1% by weight, particularly in the range of 0.01 to 0.75% by weight, and more particularly in the range of 0.025 to 0.5% by weight, based on the weight of the plastic base or a separate layer coated on the surface of the plastic base.

[0110] In particular, with respect to homopolymers or copolymers of linear, branched aliphatic, or aromatic polyols of allyl carbonate, or copolymers of polythiols and polyisocyanates, the use of light stabilizers is especially desirable if the plastic base tends to yellow. With respect to the latter (polythiourethane), the use of light stabilizers is desirable for plastic bases with a high refractive index of about 1.6, and more particularly about 1.67.

[0111] As described above, ophthalmic lenses can be manufactured according to wearer specifications and processed to provide ophthalmic lenses with diverse functions. Therefore, ophthalmic lenses may have complex structures resulting from the interlayering and / or a series of treatments of materials to tailor the ophthalmic lens to specific user requirements. For example, treatments may be carried out to reduce thickness, to lighten the ophthalmic lens, or to improve its transparency, in order to achieve durability, strength and protection, aesthetic appeal, etc. As a result, in addition to any separate layer which may contain the compound of formula (I), the ophthalmic lens may further include one or more coatings placed on the plastic base, such as impact-resistant coatings, scratch-resistant coatings, anti-reflective coatings, tint coatings, colored coatings, anti-static coatings, stain-resistant coatings, water-repellent coatings, polarizing coatings, or photochromic coatings.

[0112] The ophthalmic lens of the present invention can absorb blue light. In particular, the ophthalmic lens can block light higher than 403 nm.

[0113] In one embodiment, the ophthalmic lens may exhibit light cutoff in the range of 403-420 nm, particularly in the range of 404-411 nm.

[0114] The term "light cut," or optical cut (UV cut ) as used herein refers to the lowest wavelength in the UV-visible range that has a transmittance of more than 1% through an ophthalmic lens.

[0115] The term "transmittance," as used herein, refers to the intensity of radiation transmitted through a material divided by the intensity of incident light, and is expressed as a percentage. The transmittance of ophthalmic lenses can be measured according to ISO 8980-3-2003.

[0116] In one embodiment, the transmittance TVD65 of the ophthalmic lens is greater than 85%, and particularly greater than 87%.

[0117] The ophthalmic lens of the present invention is not subject to undesirable yellowing. In particular, the yellowness index, or YI, of the light transmitted through the ophthalmic lens may be less than 14. The yellowness index of the ophthalmic lens can be measured according to ASTM D-1925.

[0118] In particular, the yellowness index of the light transmitted through the aforementioned ophthalmic lens is 410nm UV cut It can be less than 10.

[0119] The ophthalmic lens of the present invention may have a BVC B' value of more than 25%, particularly more than 30%, and more particularly more than 35%.

[0120] The BVC B' value refers to the blue-violet cut, which is determined by excluding the transmittance in the 400-455nm range from the total transmittance in the 380-780nm range (100% - average transmittance in the spectral range of 400-455nm).

[0121] The ophthalmic lens according to the present invention exhibits good stability.

[0122] The above-mentioned ophthalmic lenses showed optical cut change (ΔUV) after exposure of the ophthalmic lenses to light for 40 hours in a Q-SUN Xe-3 xenon test chamber, with less than 2%, and especially less than 1%. cut These values ​​may be absolute values.

[0123] The above-mentioned ophthalmic lenses have a perceived color difference ΔE of less than 2.5, and especially less than 1, after the ophthalmic lenses have been exposed to light for 40 hours in a Q-SUN Xe-3 xenon test chamber. lab It may have.

[0124] ΔUV cut (%) represents the change in optical cutoff after 40 hours of accelerated aging (t40) in a Q-SUN Xe-3 xenon test chamber, relative to the initial state (t0), expressed in percentage units:

number

[0125] ΔE Lab represents the perceived color difference of the lens in the Q-SUN Xe-3 xenon test chamber at the initial state (t0) after 40 hours of accelerated aging (t40):

Number

[0126] These value colorimetric coordinates L*, a*, and b* represent colorimetric coordinates that can be measured according to the International Colorimetric System CIE(1976)L*a*b*.

[0127] In addition, and particularly when X in formula (I) is NR 15 it has been found that the ophthalmic lens is particularly stable over the long term.

[0128] Such lenses still exhibit sufficient optical properties after storage for at least one year in the dark at room temperature. They exhibit, among other things, after one year of storage: · An optical cut change ΔUV of less than 0.5% cut (these values are absolute values), and / or · A perceived color difference ΔE of less than 1 lab , and / or · A ΔBVC B’ value of less than 5% are shown.

[0129] The preparation process of the ophthalmic lens The ophthalmic lens of the present invention is a) A step of providing a monomer or oligomer that can prepare a plastic base, b) A step of mixing a monomer or oligomer with a compound of formula (I) and a catalyst suitable for polymerization of the monomer and oligomer to form a polymerizable liquid composition, c) A step of curing a polymerizable liquid composition It can be prepared by a process that includes [a certain component].

[0130] The coating can be deposited or formed by various methods, including wet processing and film transfer.

[0131] In particular, the ophthalmic lens of the present invention is a) A step of providing a monomer or oligomer that can prepare a coating layer, b) A step of mixing a monomer or oligomer with a compound of formula (I) and a catalyst suitable for polymerization of the monomer and oligomer to form a polymerizable liquid composition, c) A step of coating a substrate with a polymerizable liquid composition, d) A step of curing the polymerizable liquid composition It can be prepared by a wet process including [a specific method]. Preferably, curing is by thermal curing.

[0132] Alternatively, the ophthalmic lens of the present invention is a) A step of providing a monomer or oligomer that can prepare a coating layer, b) A step of mixing a monomer or oligomer with a compound of formula (I) and a catalyst suitable for polymerization of the monomer and oligomer to form a polymerizable liquid composition, c) A step of coating a transfer film with a polymerizable liquid composition, d) A step of curing a polymerizable liquid composition to obtain a coating layer, e) A step of transferring the coating layer from the transfer film onto the substrate. It can be prepared by a film transfer process that includes [a specific component]. Preferably, curing is by thermal curing.

[0133] Preferably, the coating layer is bonded to the substrate by an adhesive layer, such as a UV-curable adhesive, a thermosetting adhesive layer, or a pressure-sensitive adhesive layer.

[0134] According to a preferred embodiment, the polymerizable liquid composition may be stirred until homogeneous, and then degassed and / or filtered before curing. The polymerizable liquid composition of the present invention described above can be poured into a mold for forming a lens and polymerized by heating at a temperature of 10 to 150°C, particularly 15 to 130°C. According to a preferred embodiment, heating may continue for 5 to 24 hours, preferably 7 to 22 hours, and more preferably 15 to 20 hours.

[0135] Next, the mold is disassembled, and the lens can be cleaned with water, ethanol, or isopropanol.

[0136] In the process according to the present invention, a release agent may be used. The release agent prevents excessive adhesion between the lens and the mold by creating a barrier between the lens and the mold surface. Both internal and external release agents may be used in the present invention. • Internal release agents are used, for example, by adding such reagents to the monomer bulk during step b) of the process according to the present invention. Non-limiting examples of internal release agents include mono- or di-alkyl phosphates, acidic mono- or di-phosphate esters, silicones, fluorinated hydrocarbons, fatty acids, and ammonium salts. When an internal release agent is used, the reagents may be present in the prepared ophthalmic lens. External release agents are used by coating the inner surface of the mold with a surface lubricant such as siloxane and fluorinated hydrocarbons.

[0137] Next, the ophthalmic lens may be coated with one or more functional coatings selected from the group consisting of impact-resistant coatings, scratch-resistant coatings, anti-reflective coatings, tint coatings, colored coatings, anti-static coatings, stain-resistant coatings, water-repellent coatings, polarizing coatings, or photochromic coatings.

[0138] Use of the compound of formula (I) The present invention also relates to the use of a compound of formula (I) as defined above in an ophthalmic lens for absorbing blue light.

[0139] Blue light absorption can be evaluated by determining the average transmittance of an ophthalmic lens over the 420–450 nm range. Advantageously, the average transmittance of an ophthalmic lens over the 420–450 nm range is less than 85% for uncoated lenses (i.e., without anti-reflective coatings).

[0140] Composition containing acrylonitrile compounds The present invention also includes a plastic base and formula (IA): [ka] [In the formula, [In the formula, R1 is -CN, -CONH2, -CO2R6, or -SO2-(C1~C 12 ) Selected from alkyl groups, R2 is R3, R4 and R 5c Independently from, H, F, Cl, Br, I, -OH, -OR7, -SH, -SR8, -SOR9, SO2R 10 -NH2, -NHR 11 , -N(R 12 )2, -NHCOR 13 ,-NHSO2OR 14 -NO2, -CN, (C1~C 12 ) Alkyl, (C1~C 12 ) Haloalkyl, (C2~C 12 ) Alkenil, (C2~C 12) Alkinyl, (C1~C 12 ) Heteroalkyl, (C3~C 12 )Cycloalkyl, (C3~C 12 ) Heterocycloalkyl, (C6~C 18 )aryl, (C6~C 18 )Aaryl-(C1~C 12 )alkyl, or (5-10 member) heteroaryl-(C1-C 12 ) Selected from alkyl groups, R3, R4, and R5 are H, F, Cl, Br, I, -OH, -OR7, -SH, -SR8, -SOR9, SO2R 10 -NH2, -NHR 11 , -N(R 12 )2, -NHCOR 13 ,-NHSO2OR 14 -NO2, -CN, (C1~C 12 ) Alkyl, (C1~C 12 ) Haloalkyl, (C2~C 12 ) Alkenil, (C2~C 12 ) Alkinyl, (C1~C 12 ) Heteroalkyl, (C3~C 12 )Cycloalkyl, (C3~C 12 ) Heterocycloalkyl, (C6~C 18 )aryl, (C6~C 18 )Aaryl-(C1~C 12 )alkyl, (5-10 member) heteroaryl, or (5-10 member) heteroaryl-(C1-C 12 ) Selected independently from alkyl, X is NH 、 NR 15 , O, or S, R6, R7, R8, R9, R 10 , R 11 R 12 , R 13 and R 14 (C1~C 12 ) Alkyl, (C1~C 12 ) Haloalkyl, (C2~C 12 ) Alkenil, (C2~C 12 ) Alkinyl, (C1~C 12 ) Heteroalkyl, (C3~C12 )Cycloalkyl, (C3~C 12 ) Heterocycloalkyl, (C6~C 18 )aryl, (C6~C 18 )Aaryl-(C1~C 12 )alkyl, (5-10 member) heteroaryl, or (5-10 member) heteroaryl-(C1-C 12 ) Selected independently from alkyl, R 15 (C1~C 12 ) Alkyl, (C2~C 12 ) Alkenil, (C2~C 12 ) Alkinyl, (C1~C 12 ) Heteroalkyl, (C3~C 12 )Cycloalkyl, (C3~C 12 ) Heterocycloalkyl, (C6~C 18 )aryl, (C6~C 18 )Aaryl-(C1~C 12 )alkyl, (5-10 member) heteroaryl, (5-10 member) heteroaryl-(C1-C 12 )alkyl (the alkyl has 1 to 3 R 16 (Selected from those that are arbitrarily substituted by the base, R 16 These are halogen atoms, (C1~C 12 )alkoxy, (C6~C 18 ) Selected from the arrows, Or R 15 is, equation b: [ka] (In the formula, L is (C1~C 12 ) is alkylene, R 1a -CN, -CONH2, -CO2R 6a or -SO2-(C1~C 12 ) Selected from alkyl groups, R 2a R 3a , R 4a and R 5a Independently from, H, F, Cl, Br, I, -OH, -OR 7a-SH, -SR 8a -SOR 9a SO2R 10a -NH2, -NHR 11a , -N(R 12a )2, -NHCOR 13a ,-NHSO2OR 14a -NO2, -CN, (C1~C 12 ) Alkyl, (C1~C 12 ) Haloalkyl, (C2~C 12 ) Alkenil, (C2~C 12 ) Alkinyl, (C1~C 12 ) Heteroalkyl, (C3~C 12 )Cycloalkyl, (C3~C 12 ) Heterocycloalkyl, (C6~C 18 )aryl, (C6~C 18 )Aaryl-(C1~C 12 )alkyl, (5-10 member) heteroaryl, or (5-10 member) heteroaryl-(C1-C 12 ) Selected from alkyl groups, R 3a , R 4a and R 5a These are H, F, Cl, Br, I, -OH, -OR7, -SH, -SR 8a -SOR 9a SO2R 10a -NH2, -NHR 11a , -N(R 12a )2, -NHCOR 13a ,-NHSO2OR 14a -NO2, -CN, (C1~C 12 ) Alkyl, (C1~C 12 ) Haloalkyl, (C2~C 12 ) Alkenil, (C2~C 12 ) Alkinyl, (C1~C 12 ) Heteroalkyl, (C3~C 12 )Cycloalkyl, (C3~C 12 ) Heterocycloalkyl, (C6~C 18 )aryl, (C6~C 18 )Aaryl-(C1~C 12 )alkyl, (5-10 member) heteroaryl, or (5-10 member) heteroaryl-(C1-C12 ) Selected independently from alkyl, R 6a , R 7a , R 8a , R 9a , R 10a , R 11a , R 12a , R 13a and R 14a (C1~C 12 ) Alkyl, (C1~C 12 ) Haloalkyl, (C2~C 12 ) Alkenil, (C2~C 12 ) Alkinyl, (C1~C 12 ) Heteroalkyl, (C3~C 12 )Cycloalkyl, (C3~C 12 ) Heterocycloalkyl, (C6~C 18 )aryl, (C6~C 18 )Aaryl-(C1~C 12 )alkyl, (5-10 member) heteroaryl, or (5-10 member) heteroaryl-(C1-C 12 (Selected independently of alkyl) It is the structure or The aryl or heteroaryl group is optionally substituted by one or more substituents, particularly by one or two substituents, wherein the substituents are: • Halogens, especially F or Cl, • Carboxylic acid esters, especially methyl esters or ethyl esters, (C1~C 12 ) Alkyl, especially methyl, ethyl or isopropyl, (C1~C 12 ) Alkoxy, especially methoxy or ethoxy, • Carboxylic acid, Nitrile, • Amines, especially -NH2, NHCH3, or N(CH3)2 [Selected from] A composition comprising the compound, The plastic base is as defined above. Regarding compositions.

[0141] The present invention also relates to the use of compositions as defined above in optical articles.

[0142] The uses of the present invention relate particularly to optical articles such as optical lenses, display devices, optical filters, window glass, protective adhesives and films, especially ophthalmic lenses, or display devices such as computer screens or TV screens.

[0143] In particular, the composition according to the present invention is used in the optical article to absorb blue light.

[0144] The present invention further, [ka] This relates to novel compounds or salts thereof selected from the following.

[0145] The present invention will now be described in more detail using the following embodiments, which are provided purely for illustrative purposes and are not intended to limit the scope of the invention in any way.

[0146] The present invention will now be described in more detail with reference to the following figures and examples, which are provided purely for illustrative purposes and are not intended to limit the scope of the invention in any way. [Brief explanation of the drawing]

[0147] [Figure 1] This graph shows the absorbance (A) as a function of wavelength (λ, in nm) for a solution of the compounds (I-1) to (I-7) at a concentration of 20 ppm in tetrahydrofuran. [Modes for carrying out the invention]

[0148] Examples Method for measuring the optical performance and light resistance of lenses. The optical properties of the lens were measured using a Cary60 UV-Vis spectrophotometer with scanning wavelengths of 280-780 nm for a flat lens with a center thickness of 2 mm. Photoaging tests were performed using Q-sun (40 h, light output 0.68 W / m²). 2 ) was performed. The optical value was UV cut Examples include TvD65, YI, C*, h*, a*, b*, and BVC B'. UV cut This is determined under perpendicularly incident light by plotting a graph of the lens's transmittance percentage as a function of wavelength. cut This can be read on the graph as the lowest wavelength from the spectrum where the transmittance through the ophthalmic lens is greater than 1%. • TVD65 is determined under perpendicularly incident light (standard luminaire D65). BVC B' is determined by subtracting the transmittance in the 400-455nm range from the total transmittance in the 380-780nm range (100% - average transmittance in the spectral range of 400-455nm). • YI is measured according to ASTM D1925. The colorimetric coordinates L*, a*, b*, C*, and h* of the lens of the present invention were measured using a D65 light source and 10 observers, according to the International Colorimetric System (CIE) L*a*b* and L*C*h* International Colorimetric System; the measured parameters were: L* corresponds to brightness. a* value indicating the red-green component b* value indicating the yellow-blue component C* represents the saturation of a color. h* represents the angle on the chromaticity axis. That is the case.

[0149] Lightfastness testing using the Q-sun method was performed on a flat lens with a center thickness of 2 mm, using the Q-sun Xe-1 model: light intensity of 0.68 W / m2 at 340 nm, temperature of 60°C, sunlight Q-UV filter, and a 40-hour running cycle. Lens lightfastness was assessed based on two main aspects: lens optical cut change (ΔUV). cut ) and color progression (ΔE LabThe values ​​were certified as follows: The values ​​were obtained by comparing the values ​​measured after manufacturing (t0) with the values ​​after 40 hours of accelerated aging in the Q-sun cell (t40).

[0150] material In this example, the following compounds are used.

[0151] [Table 1]

[0152] [Table 2]

[0153] Example 1: Preparation of compounds (I-1) to (I-7) The following compounds (I-1) to (I-7) were prepared by Knoebener condensation. [ka]

[0154] Preparation of I-1 Compound I-1 is reacted using the following scheme: [ka] It was prepared according to the following procedure. In short, 3,5-dimethyl-1H-pyrrole-2-carbaldehyde was reacted with ethyl cyanoethyl in ethanol at room temperature in the presence of piperidine.

[0155] Preparation of I-2 Compound I-2 was prepared using the same reaction conditions as Compound I-1, but with the reactant ethyl cyanoethyl replaced by malononitrile.

[0156] Preparation of I-3 Compound I-3 is reacted using the following scheme: [ka] It was prepared according to the following procedure. In short, pyrrole-2-carboxyaldehyde was reacted with malonitrile in water at room temperature.

[0157] Preparation of I-4 Compound I-4 was prepared using the same reaction conditions as compound I-3, but with the reactant pyrrole-2-carboxyaldehyde replaced by 1-methyl-1H-pyrrole-2-carboxyaldehyde.

[0158] Preparation of I-5 Compound I-5 was prepared using the same reaction conditions as Compound I-3, but with the reactant pyrrole-2-carboxyaldehyde replaced by 5-methyl-1H-pyrrole-2-carboxyaldehyde.

[0159] Preparation of I-6 [ka] Compound I-6 was prepared using the same reaction conditions as compound I-3, but by replacing the reactant pyrrole-2-carboxyaldehyde with 1-(2-ethylhexyl)-1H-pyrrole-2-carboxyaldehyde. The latter was prepared by alkylating 1H-pyrrole-2-carboxyaldehyde with 2-ethylhexyl bromide in dimethylformamide in the presence of sodium hydride.

[0160] Preparation of I-7 Compound I-7 was prepared by alkylating pyrrole-2-carboxyaldehyde with 1,3-dibromopropane, resulting in the substitution of two bromide groups. The two aldehyde groups were then reacted under the same reaction conditions as for compound I-3 to form compound I-7: [ka]

[0161] Example 2: Absorption characteristics of compounds (I-1) to (I-7) The absorbance (A) as a function of wavelength (λ) was measured for a solution of 0.02 mg of the compounds of formulas (I-1) to (I-7) in 1 mL of tetrahydrofuran. The obtained absorption spectra are shown in Figure 1. For each compound, the maximum absorption wavelength (λ) was measured. max The absorption coefficient (ε) at the maximum absorption wavelength is shown in Table 1 below.

[0162] [Table 3]

[0163] All compounds according to the present invention have a maximum absorption wavelength (λ) in the range of 360 to 400 nm. max ) is shown. In addition, the compounds according to the present invention exhibit a greater extinction coefficient at the maximum absorption wavelength than the comparative prior art compounds H-Oxa and Seesorb® 703.

[0164] Example 3: Preparation of a composition for obtaining an ophthalmic lens having a refractive index of 1.67 Compositions 1 to 8 and comparative compositions Comp. 1 to 3 according to the present invention were prepared, containing the following components. The values ​​shown in Table 2 are weight percentages based on the total weight of the compositions.

[0165] [Table 4]

[0166] [Table 5]

[0167] The composition is prepared in the following steps: 1) A release agent (Zelec® UN), a catalyst (DMC), a UV absorber (Seesorb® 701), and a blue-cut molecule of formula (I) were dissolved in an ISO2 monomer in a Duran® bottle at room temperature. After homogenization, the mixture was degassed under vacuum. 2) The resulting mixture was pre-cooled to 2°C and placed in an N2 atmosphere. 3) Add the THIO2 monomer and stir the mixture at 2°C until a homogeneous mixture is formed, then degas it, purge with N2, and then carry out the monomer packing step. It was prepared according to the instructions.

[0168] Example 4: Preparation of an ophthalmic lens having a refractive index of 1.67 A flat glass mold was assembled by taping to accommodate a lens with a center thickness of 2 mm. The monomer mixture of Example 3 was then injected into the prepared assembly using a clean syringe and thermally polymerized using a specific temperature profile as shown in Table 3.

[0169] [Table 6]

[0170] The lenses were generally disassembled from their molds and subjected to traditional cleaning and annealing processes.

[0171] Example 5: Preparation of a composition for obtaining an ophthalmic lens having a refractive index of 1.6 Compositions 9-14 and comparative compositions Comp.4-6 according to the present invention were prepared, containing the following components. The values ​​shown in the following table are weight percentages based on the total weight of the composition. The values ​​shown in Table 4 below are weight percentages based on the total weight of the composition. The preparation process for these compositions was similar to that of compositions 1-8 in Example 3, in that all additives were dissolved in ISO1 monomer, followed by degassing and pre-cooling, and then THIO1 and THIO2 monomers were added.

[0172] [Table 7]

[0173] Example 6: Preparation of an ophthalmic lens having a refractive index of 1.6 According to Example 4, an ophthalmic lens with a refractive index of 1.6 was prepared using the same procedure as for a lens with a refractive index of 1.67. The specific temperature profiles are shown in Table 5.

[0174] [Table 8]

[0175] The lenses were generally disassembled from their molds and subjected to traditional cleaning and annealing processes.

[0176] Example 7: Optical properties of the lens The BCT lenses of Examples 4 and 6 were optically characterized at the initial lens stage and after photoaging testing.

[0177] The initial optical properties of a lens with a refractive index of 1.67 are shown in Table 6 below.

[0178] [Table 9]

[0179] The results of the photoaging test on a lens with a refractive index of 1.67 are shown in Table 7 below.

[0180] [Table 10]

[0181] The lens according to the present invention, having a refractive index of 1.67, has two meanings: 1) Lower molecular consumption at the same optical cut due to a higher absorption extinction coefficient 2) In both counts, namely optical cut and color retention, it performs better than the comparison lens in terms of superior lightfastness. On the other hand, for fresh lenses, it maintains excellent aesthetics comparable to the reference lens. Specifically, Example 3 doped with I-3 required 3.7 times less absorber content than that of comparison Comp.1 and even less than Comp.3 to provide the same optical cut performance (408nm) without aesthetic trade-offs in a similar range of residual color YI (5-6). Moreover, the degree of optical cut (%ΔUV) cut The characteristic durability of Example 3 over photoaging, defined by the ↓ and color change (ΔE↓), is greater than that of Comp.1.

[0182] The initial optical properties of a lens with a refractive index of 1.6 are shown in Table 8 below.

[0183] [Table 11]

[0184] The results of the photoaging test on a lens with a refractive index of 1.6 are shown in Table 9 below.

[0185] [Table 12]

[0186] Consistent with a lens having a refractive index of 1.67, the lens according to the present invention, having a refractive index of 1.6, has higher lightfastness compared to several comparative lens examples, and is more industrial and economical, i.e., requires a lower absorber content for the same cut range.

[0187] Example 8: Optical properties of the lens In this embodiment, the long-term stability of the lens was investigated. In addition, the thermal and optical stability of the lens were examined after long-term storage.

[0188] Example 8a: Preparation of lenses for storage studies A lens having a refractive index of 1.67 was prepared according to the procedure described in Example 3. The lens prepared in this example contains the following compound: [ka] It included.

[0189] The lens composition is as shown in Table 10.

[0190] [Table 13]

[0191] Example 8b: Initial lens characteristics before storage The optical properties of the lenses in their initial state, as described in Example 8a and Table 10, were determined using the same procedure as in Example 3. The results are shown in Table 11 below.

[0192] [Table 14]

[0193] Example 8c: Lens characteristics after storage - Overview and method The lenses of Example 8a, after casting and post-curing, were stored in an envelope at ambient temperature in the dark for approximately 1.2 years, and their optical properties were remeasured using a UV-Vis spectrometer. The stability of the lens properties after storage was measured using ΔE. Lab Color changes using parameters, as well as ΔBVCB' and ΔUV cut We investigated this from the perspective of changes in blue-cut capability using ΔE. Lab If ΔBVCB' is less than 1%, it is defined herein as an acceptable / insignificant change. If ΔBVCB' is less than 5%, it is defined as an acceptable / insignificant change. ΔUV cut If it is less than 0.5%, it is defined herein as an acceptable / insignificant change.

[0194] For the experiments described herein, ΔE Lab ΔBVCB' and ΔUVcut were calculated as follows. • General calculation of the amplitude of color change (equation a)

number

number

number

[0195] Thermal stability testing of stored lenses The above 1.2-year stored lenses were analyzed using a UV-Vis spectrometer and then subjected to heating at 95°C for 3 hours, mimicking the thermal conditions of the hard coating process. The lenses were then cooled and left in the open for at least 1 hour to allow for relaxation. The optical properties of the tested lenses were then remeasured using a UV-Vis spectrometer. The color shift and cut performance of the 1.2-year-old lenses during the thermal test were expressed using equations a, b, and c, with respect to the aforementioned parameter (ΔE Lab ΔBVCB' and ΔUV cutThe values ​​were expressed by the following equations: General equations a, b, and c were adapted to calculate these parameters. i0 refers to the value of the 1.2-year-old lens (measured immediately before the heat test), and i refers to the value after the heat test.

[0196] Lightstability testing of stored lenses The properties of lenses stored under photoaging were investigated to predict the robustness of aging lenses over time. The photoaging test was performed using the Q-sun test as described above (80 hours). Similarly, the optical properties of such 1.2-year stored lenses were measured before and after 80-hour cycles of the Q-sun test to determine the degree of change in color and cut performance over the test. The degree of change was quantified according to equations a, b, and c, respectively, where i0 refers to the value of the 1.2-year-old lens (measured immediately before the Q-sun test) and i refers to the value of the lens after 80-hour cycles of the Q-sun test.

[0197] Example 8d: Results of storage stability test The results of the above thermal and optical tests are shown in Table 12.

[0198] [Table 15]

[0199] From Table 12, it can be concluded that, overall, lenses 15-18 according to the present invention showed improved thermal and photostability after storage compared to comparative lenses containing oxazolone (Tests II and III). In particular, lenses made with compounds I-4, I-6, and I-7 showed particularly high stability. These lenses containing N-alkyl-substituted pyrrole acrylonitrile were shown to be particularly stable under storage and post-thermal and photostability conditions when compared to comparative lenses containing oxazolone and lenses containing unsubstituted pyrrole acrylonitrile on nitrogen (I-3 and I-5). In particular, lenses cast using N-alkyl-substituted I-4 and I-6 showed high robustness in all counts; they showed acceptable color and cut capability over time and through post-conditioning, i.e., heat and light steps after maturation time.

Claims

1. It is an ophthalmic lens, - Plastic base and, - Compounds of formula (I) or salts thereof, especially hydrochloride or sulfate salts and Includes, 【Chemistry 1】 During the ceremony: R １ -CN, -CONH ２ , -CO ２ R ６ or -SO ２ - (C １ ~C １２ ) Selected from alkyl groups, R ２ is independently selected from R ３ , R ４ and R ５ and is selected from H, F, Cl, Br, I, -OH, -OR ７ , -SH, -SR ８ , -SOR ９ , SO ２ R １０ , -NH ２ , -NHR １１ , -N(R １２ ) ２ , -NHCOR １３ , -NHSO ２ OR １４ , -NO ２ , -CN, (C １ ~C １２ ) alkyl, (C １ ~C １２ ) haloalkyl, (C ２ ~C １２ ) alkenyl, (C ２ ~C １２ ) alkynyl, (C １ ~C<着 １２ ) heteroalkyl, (C ３ ~C １２ ) cycloalkyl, (C ３ ~C １２ ) heterocycloalkyl, (C ６ ~C １８ ) aryl, (C ６ ~C １８ ) aryl-(C<0着000043>~C １２ ) alkyl, (5-10 member) heteroaryl or (5-10 member) heteroaryl-(C １ ~C １２ ) alkyl, It should be noted that there may be some inaccuracies in the original text, especially in the chemical formula part. It is recommended to double-check with the original source for more accurate content. R ３ , R ４ and R ５ is H, F, Cl, Br, I, -OH, -OR ７ -SH, -SR ８ , -SOR ９ SO ２ R １０ , -NH ２ , - NHR １１ , -N(R １２ ) ２ ,-NHCOR １３ , - NHSO ２ OR １４ , -NO ２ ,-CN,(C １ ~C １２ ) alkyl, (C １ ~C １２ ) Haloalkyl, (C ２ ~C １２ ) Alkenil, (C ２ ~C １２ ) Alkinnil, (C １ ~C １２ ) Heteroalkyl, (C ３ ~C １２ ) Cycloalkyl, (C ３ ~C １２ ) Heterocycloalkyl, (C ６ ~C １８ ) Aryl, (C ６ ~C １８ ) Ariel-(C １ ~C １２ ) alkyl, (5-10 member) heteroaryl or (5-10 member) heteroaryl-(C １ ~C １２ ) Selected independently from alkyl, X is NH, NR １５ , O, or S, R ６ 、R ７ 、R ８ 、R ９ 、R １０ 、R １１ 、R １２ 、R １３ and R １４ are independently selected from (C １ ~C １２ )alkyl, (C １ ~C １２ )haloalkyl, (C ２ ~C １２ )alkenyl, (C ２ ~C １２ )alkynyl, (C １ ~C １２ )heteroalkyl, (C ３ ~C １２ )cycloalkyl, (C ３ ~C １２ )heterocycloalkyl, (C ６ ~C １８ )aryl, (C ６ ~C １８ )aryl-(C １ ~C １２ )alkyl, (5- to 10-membered)heteroaryl or (5- to 10-membered)heteroaryl-(C １ ~C １２ )alkyl, R １５ is, (C １ ~C １２ ) alkyl, (C ２ ~C １２ ) Alkenil, (C ２ ~C １２ ) Alkinyl, (C １ ~C １２ ) Heteroalkyl, (C ３ ~C １２ ) Cycloalkyl, (C ３ ~C １２ ) Heterocycloalkyl, (C ６ ~C １８ ) Aryl, (C ６ ~C １８ ) Ariel-(C １ ~C １２ ) alkyl, (5-10 member) heteroaryl, (5-10 member) heteroaryl-(C １ ~C １２ ) Alkyl (The alkyl has 1 to 3 R １６ Selected from (which are arbitrarily substituted by the base), R １６ (C) is a halogen atom. １ ~C １２ ) Alkoxy, (C ６ ~C １８ ) Selected from the arrows, Or R １５ Equation a: 【Chemistry 2】 (In the formula, L is (C １ ~C １２ ) is alkylene, R １ａ -CN, -CONH ２ , -CO ２ R ６ａ or -SO ２ - (C １ ~C １２ ) Selected from alkyl groups, R ２ａ R ３ａ , R ４ａ and R ５ａ Independently from, H, F, Cl, Br, I, -OH, -OR ７ａ -SH, -SR ８ａ , -SOR ９ａ SO ２ R １０ａ , -NH ２ , - NHR １１ａ , -N(R １２ａ ) ２ ,-NHCOR １３ａ , - NHSO ２ OR １４ａ , -NO ２ ,-CN,(C １ ~C １２ ) alkyl, (C １ ~C １２ ) Haloalkyl, (C ２ ~C １２ ) Alkenil, (C ２ ~C １２ ) Alkinyl, (C １ ~C １２ ) Heteroalkyl, (C ３ ~C １２ ) Cycloalkyl, (C ３ ~C １２ ) Heterocycloalkyl, (C ６ ~C １８ ) Aryl, (C ６ ~C １８ ) Ariel-(C １ ~C １２ ) alkyl, (5-10 member) heteroaryl or (5-10 member) heteroaryl-(C １ ~C １２ ) Selected from alkyl groups, R ３ａ , R ４ａ and R ５ａ is H, F, Cl, Br, I, -OH, -OR ７ -SH, -SR ８ａ , -SOR ９ａ SO ２ R １０ａ , -NH ２ , - NHR １１ａ , -N(R １２ａ ) ２ ,-NHCOR １３ａ , - NHSO ２ OR １４ａ , -NO ２ ,-CN,(C １ ~C １２ ) alkyl, (C １ ~C １２ ) Haloalkyl, (C ２ ~C １２ ) Alkenil, (C ２ ~C １２ ) Alkinyl, (C １ ~C １２ ) Heteroalkyl, (C ３ ~C １２ ) Cycloalkyl, (C ３ ~C １２ ) Heterocycloalkyl, (C ６ ~C １８ ) Aryl, (C ６ ~C １８ ) Ariel-(C １ ~C １２ ) alkyl, (5-10 member) heteroaryl or (5-10 member) heteroaryl-(C １ ~C １２ ) Selected independently from alkyl, R ６ａ , R ７ａ , R ８ａ , R ９ａ , R １０ａ , R １１ａ , R １２ａ , R １３ａ and R １４ａ is, (C １ ~C １２ ) alkyl, (C １ ~C １２ ) Haloalkyl, (C ２ ~C １２ ) Alkenil, (C ２ ~C １２ ) Alkinyl, (C １ ~C １２ ) Heteroalkyl, (C ３ ~C １２ ) Cycloalkyl, (C ３ ~C １２ ) Heterocycloalkyl, (C ６ ~C １８ ) Aryl, (C ６ ~C １８ ) Ariel-(C １ ~C １２ ) alkyl, (5-10 member) heteroaryl or (5-10 member) heteroaryl-(C １ ~C １２ (Selected independently of alkyl) It has the following structure: The aryl or heteroaryl group is optionally substituted by one or more substituents, particularly by one or two substituents, wherein the substituents are: Halogens, especially F or Cl, • Carboxylic acid esters, especially methyl esters or ethyl esters, ・ (C １ ~C １２ ) Alkyl, especially methyl, ethyl or isopropyl, ・ (C １ ~C １２ ) Alkoxy, especially methoxy or ethoxy, • Carboxylic acid, Nitrile, • Amines, especially -NH ２ , NHCH ３ , or N(CH ３ ) ２ Selected from, Eye lenses.

2. R １ and R １ａ is -CN or -CO ２ Selected independently of Et, and / or R ２ , R ２ａ , R ３ , R ３ａ , R ４、 R ４ａ , R ５ and R ５ａ is H or (C １ ~C １２ ) Alkyl, preferably H or CH ３ An ophthalmic lens according to claim 1, which is independently selected from the above.

3. X is NH or NR １５ , especially NH or -NCH ３ , -NCH ３ CH ３ -N-CH ２ C (CH ２ CH ３ ) (CH ２ ) ３ CH ３ , -NC (CH ３ ) ３ , -NCH ２ -CF ３ , N (CH ２ ) ２ -phenyl, N-(CH ２ ) ４ -F or N- (CH ２ ) ４ - OCH ３ And, R １５ The ophthalmic lens according to claim 1 or 2, wherein the ophthalmic lens is as defined in claim 1.

4. The compound of formula (I) is R １ is -CN, and X is -NR １５ And, R １５ However, as defined in claim 1, and especially halogen atoms, (C １ ~C １２ ) Alkoxy, (C ６ ~C １８ ) One to three R selected from the aryl group １６ -(C) which is optionally substituted by the base. １ ~C １２ ) Particularly selected from alkyl groups Or R １ａ is -CN, R ２ａ , R ３ａ , R ４ａ and R ５ａ The compound is of formula a as defined in claim 1, wherein H is An ophthalmic lens according to any one of claims 1 to 3.

5. The compound of formula (I) is R １ is -CN, R ２ , R ３ , R ４ and R ５ H is, X is -NR １５ And, R １５ However, as defined in claim 1, and especially halogen atoms, (C １ ~C １２ ) Alkoxy, (C ６ ~C １８ ) One to three R selected from the aryl group １６ -(C) which is optionally substituted by the base. １ ~C １２ ) Particularly selected from alkyl groups, Or R １ａ is -CN, R ２ａ , R ３ａ , R ４ａ and R ５ａ An ophthalmic lens according to any one of claims 1 to 4, wherein the compound is of formula a as defined in claim 1, and is H.

6. The compounds of formula (I) are formulas I-1 to I-7: 【Transformation 3】 An ophthalmic lens according to any one of claims 1 to 5, selected from the compounds.

7. The compound of formula (I) has a maximum absorption wavelength (λ) of 400 nm or less, as measured with respect to a 20 ppm solution of the compound of formula I in an organic solvent, particularly tetrahydrofuran. ｍａｘ An ophthalmic lens according to any one of claims 1 to 6, wherein the maximum absorption wavelength is particularly in the range of 350 to 400 nm, and more particularly in the range of 370 to 400 nm.

8. The maximum absorption wavelength (λ ｍａｘ In the above, the compound of formula (I) is 30,000 M －１ cm －１ It has a higher molar absorption extinction coefficient (ε), and the molar absorption extinction coefficient (ε) is particularly in the range of 30,000 to 80,000 M －１ cm －１ In the range of 30,000 to 70,000 M －１ cm －１ Within that range, and even more specifically 30,000 to 45,000 M －１ cm －１ An ophthalmic lens according to claim 7, which is within the range of [specified range].

9. The ophthalmic lens according to any one of claims 1 to 8, wherein the compound of formula (I) is contained in the plastic base or in a separate layer coated on the surface of the plastic base.

10. An ophthalmic lens according to any one of claims 1 to 9, wherein the amount of the compound of formula (I) is in the range of 0.001 to 2% by weight, particularly 0.001 to 1% by weight, more particularly 0.001 to 0.1% by weight, and even more particularly 0.01 to 0.05% by weight, based on the weight of the plastic base if the compound of formula (I) is contained in the plastic base, or the weight of the separate layer if the compound of formula (I) is contained in a separate layer coated on the surface of the plastic base.

11. The ophthalmic lens according to any one of claims 1 to 10, further comprising a benzotriazole UV absorber or a mixture thereof, preferably a benzotriazole UV absorber selected from 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chloro-2H-benzotriazole, and mixtures thereof, wherein the total amount of the benzotriazole UV absorber is in the range of 0.001 to 2% by weight, particularly 0.01 to 1.5% by weight, and more particularly 0.1 to 1.25% by weight, based on the weight of the plastic base.

12. The ophthalmic lens according to any one of claims 1 to 11, wherein the plastic base is a thermosetting resin or thermoplastic resin, in particular a thermosetting resin comprising a copolymer of at least one polythiol and a polyisocyanate, and / or the plastic base has a refractive index of 1.4 to 1.9, particularly 1.49 to 1.

74.

13. UV ｃｕｔ This is higher than 403 nm, particularly included in the range of 403–420 nm, and more particularly included in the range of 404–411 nm, and / or The transmittance TvD65 of the aforementioned ophthalmic lens is greater than 85%, particularly greater than 87%, and / or The yellowness index YI is less than 14, and / or The BVC B' value is greater than 25%, especially greater than 30%, and even more especially greater than 35%. An ophthalmic lens according to any one of claims 1 to 12.

14. Change in optical cutoff (ΔUV) of the ophthalmic lens after 40 hours of exposure to light in a Q-SUN Xe-3 xenon test chamber. ｃｕｔ is less than 2%, especially less than 1%, and / or Perceived color difference ΔE after the ophthalmic lens was exposed to light for 40 hours in a Q-SUN Xe-3 xenon test chamber. ｌａｂ It is less than 2.5, especially less than 1. An ophthalmic lens according to any one of claims 1 to 13.

15. A process for preparing an ophthalmic lens according to any one of claims 1 to 14, a) A step of providing a monomer or oligomer that can prepare the plastic base, b) A step of mixing the monomer or oligomer, the compound of formula (I), and a catalyst suitable for polymerization of the monomer and oligomer to form a polymerizable liquid composition, c) A step of curing the polymerizable liquid composition A process that includes this.

16. Use of a compound of formula (I) as defined in any one of claims 1 to 14 in an ophthalmic lens for absorbing blue light.

17. It comprises a plastic base and a compound of formula (IA), 【Chemistry 4】 During the ceremony: R １ -CN, -CONH ２ , -CO ２ R ６ or -SO ２ - (C １ ~C １２ ) Selected from alkyl groups, R ２ R ３ , R ４ and R ５ Independently from, H, F, Cl, Br, I, -OH, -OR ７ -SH, -SR ８ , -SOR ９ SO ２ R １０ , -NH ２ , - NHR １１ , -N(R １２ ) ２ ,-NHCOR １３ , - NHSO ２ OR １４ , -NO ２ ,-CN,(C １ ~C １２ ) alkyl, (C １ ~C １２ ) Haloalkyl, (C ２ ~C １２ ) Alkenil, (C ２ ~C １２ ) Alkinyl, (C １ ~C １２ ) Heteroalkyl, (C ３ ~C １２ ) Cycloalkyl, (C ３ ~C １２ ) Heterocycloalkyl, (C ６ ~C １８ ) Aryl, (C ６ ~C １８ ) Ariel-(C １ ~C １２ ) alkyl, or (5-10 member) heteroaryl-(C １ ~C １２ ) Selected from alkyl groups, R ３ , R ４ and R ５ is H, F, Cl, Br, I, -OH, -OR ７ -SH, -SR ８ , -SOR ９ SO ２ R １０ , -NH ２ , - NHR １１ , -N(R １２ ) ２ ,-NHCOR １３ , - NHSO ２ OR １４ , -NO ２ ,-CN,(C １ ~C １２ ) alkyl, (C １ ~C １２ ) Haloalkyl, (C ２ ~C １２ ) Alkenil, (C ２ ~C １２ ) Alkinyl, (C １ ~C １２ ) Heteroalkyl, (C ３ ~C １２ ) Cycloalkyl, (C ３ ~C １２ ) Heterocycloalkyl, (C ６ ~C １８ ) Aryl, (C ６ ~C １８ ) Ariel-(C １ ~C １２ ) alkyl, (5-10 member) heteroaryl or (5-10 member) heteroaryl-(C １ ~C １２ ) Selected independently from alkyl, X is NH, NR １５ , O, or S, R ６ , R ７ , R ８ , R ９ , R １０ , R １１ , R １２ , R １３ and R １４ is, (C １ ~C １２ ) alkyl, (C １ ~C １２ ) Haloalkyl, (C ２ ~C １２ ) Alkenil, (C ２ ~C １２ ) Alkinyl, (C １ ~C １２ ) Heteroalkyl, (C ３ ~C １２ ) Cycloalkyl, (C ３ ~C １２ ) Heterocycloalkyl, (C ６ ~C １８ ) Aryl, (C ６ ~C １８ ) Ariel-(C １ ~C １２ ) alkyl, (5-10 member) heteroaryl or (5-10 member) heteroaryl-(C １ ~C １２ ) Selected independently from alkyl, R １５ is, (C １ ~C １２ ) alkyl, (C ２ ~C １２ ) Alkenil, (C ２ ~C １２ ) Alkinyl, (C １ ~C １２ ) Heteroalkyl, (C ３ ~C １２ ) Cycloalkyl, (C ３ ~C １２ ) Heterocycloalkyl, (C ６ ~C １８ ) Aryl, (C ６ ~C １８ ) Ariel-(C １ ~C １２ ) alkyl, (5-10 member) heteroaryl, (5-10 member) heteroaryl-(C １ ~C １２ ) Alkyl (The alkyl has 1 to 3 R １６ Selected from (which are arbitrarily substituted by the base), R １６ (C) is a halogen atom. １ ~C １２ ) Alkoxy, (C ６ ~C １８ ) Selected from the arrows, Or R １５ Equation b: 【Transformation 5】 (In the formula, L is (C １ ~C １２ ) is alkylene, R １ａ -CN, -CONH ２ , -CO ２ R ６ａ or -SO ２ - (C １ ~C １２ ) Selected from alkyl groups, R ２ａ R ３ａ , R ４ａ and R ５ａ Independently from, H, F, Cl, Br, I, -OH, -OR ７ａ -SH, -SR ８ａ , -SOR ９ａ SO ２ R １０ａ , -NH ２ , - NHR １１ａ , -N(R １２ａ ) ２ ,-NHCOR １３ａ , - NHSO ２ OR １４ａ , -NO ２ ,-CN,(C １ ~C １２ ) alkyl, (C １ ~C １２ ) Haloalkyl, (C ２ ~C １２ ) Alkenil, (C ２ ~C １２ ) Alkinyl, (C １ ~C １２ ) Heteroalkyl, (C ３ ~C １２ ) Cycloalkyl, (C ３ ~C １２ ) Heterocycloalkyl, (C ６ ~C １８ ) Aryl, (C ６ ~C １８ ) Ariel-(C １ ~C １２ ) alkyl, (5-10 member) heteroaryl or (5-10 member) heteroaryl-(C １ ~C １２ ) Selected from alkyl groups, R ３ａ , R ４ａ and R ５ａ is H, F, Cl, Br, I, -OH, -OR ７ -SH, -SR ８ａ , -SOR ９ａ SO ２ R １０ａ , -NH ２ , - NHR １１ａ , -N(R １２ａ ) ２ ,-NHCOR １３ａ , - NHSO ２ OR １４ａ , -NO ２ ,-CN,(C １ ~C １２ ) alkyl, (C １ ~C １２ ) Haloalkyl, (C ２ ~C １２ ) Alkenil, (C ２ ~C １２ ) Alkinyl, (C １ ~C １２ ) Heteroalkyl, (C ３ ~C １２ ) Cycloalkyl, (C ３ ~C １２ ) Heterocycloalkyl, (C ６ ~C １８ ) Aryl, (C ６ ~C １８ ) Ariel-(C １ ~C １２ ) alkyl, (5-10 member) heteroaryl or (5-10 member) heteroaryl-(C １ ~C １２ ) Selected independently from alkyl, R ６ａ , R ７ａ , R ８ａ , R ９ａ , R １０ａ , R １１ａ , R １２ａ , R １３ａ and R １４ａ is, (C １ ~C １２ ) alkyl, (C １ ~C １２ ) Haloalkyl, (C ２ ~C １２ ) Alkenil, (C ２ ~C １２ ) Alkinyl, (C １ ~C １２ ) Heteroalkyl, (C ３ ~C １２ ) Cycloalkyl, (C ３ ~C １２ ) Heterocycloalkyl, (C ６ ~C １８ ) Aryl, (C ６ ~C １８ ) Ariel-(C １ ~C １２ ) alkyl, (5-10 member) heteroaryl or (5-10 member) heteroaryl-(C １ ~C １２ (Selected independently of alkyl) It has the following structure: The aryl or heteroaryl group is optionally substituted by one or more substituents, particularly by one or two substituents, wherein the substituents are: Halogens, especially F or Cl, • Carboxylic acid esters, especially methyl esters or ethyl esters, ・ (C １ ~C １２ ) Alkyl, especially methyl, ethyl or isopropyl, ・ (C １ ~C １２ ) Alkoxy, especially methoxy or ethoxy, • Carboxylic acid, Nitrile, • Amines, especially -NH ２ , NHCH ３ , or N(CH ３ ) ２ Selected from, The plastic base is as defined in any one of claims 1 to 12. composition.

18. Use of the composition according to claim 17 in an optical article.

19. below: 【Transformation 6】 A compound selected from or a salt thereof.

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