Azacoumarin and azathiocoumarin derivatives for use in optically active devices.

Abstract

The present invention relates to polymerized compounds containing photoactive chromophores, and novel ophthalmic devices comprising the polymerized compounds and specific monomeric compounds that are particularly suitable for compositions and ophthalmic devices. The present invention also relates to processes for altering the optical properties of the ophthalmic devices or precursor articles for making the ophthalmic devices.

Description

[Technical Field]

[0001] The present invention relates to novel ophthalmic devices comprising polymerized compounds containing photoactive chromophores and specific monomeric compounds that are particularly suitable for compositions and ophthalmic devices. The present invention also relates to processes for altering the optical properties of the ophthalmic devices or precursor articles for making the ophthalmic devices. [Background technology]

[0002] Cataract is a general term for an eye disease that causes the normally clear lens of the eye to become cloudy, impairing vision and, in severe cases, leading to blindness. Cataracts are the leading cause of blindness worldwide, affecting over 100 million people. Due to the fact that its primary cause is aging and the average age of the population is increasing, the number of cataracts is expected to continue to increase substantially in the future.

[0003] Effective treatment of cataracts is only possible through surgical intervention, in which the eye's natural lens is removed through an incision in the cornea and replaced with an ophthalmic device, often referred to as an "intraocular lens." Current state-of-the-art surgical techniques use eye mapping in preparation for surgery to approximate the optimal refractive power for each patient.

[0004] Although cataract surgery is one of the most widely used and safest surgical procedures, it is not without its own set of postoperative problems. Often, the refractive power of the implanted intraocular lens (IOL) is insufficient to restore good vision. Such problems can be caused, for example, by changes in the shape of the eye as a result of the surgery, as well as irregular wound healing and positioning errors that result in an ophthalmic device with suboptimal optical properties. As a result, patients may still require corrective vision aids, such as eyeglasses, to see properly. In some cases, the refractive power produced by the implanted ophthalmic device falls far short of the required refractive power, necessitating further surgery. Because the body's healing ability decreases with age, further surgery is undesirable, especially in the elderly. Furthermore, there is a risk of inducing endophthalmitis, an inflammation of the eye, which can lead to complete loss of vision or, worse, the loss of the eye.

[0005] Thus, there is a public health need for optically active ophthalmic devices, particularly artificial intraocular lenses, that allow for non-invasive adjustment of the refractive power after implantation of the lens, thereby preferably further reducing the need for post-operative visual aids.

[0006] Some developments in this respect have already been made, as evidenced for example by WO 2007 / 033831, WO 2009 / 074520, US 2010 / 0324165, WO 2017 / 032442, WO 2017 / 032443, WO 2017 / 032444, WO 2018 / 149850, WO 2018 / 149852, WO 2018 / 149853, WO 2018 / 149855, WO 2018 / 149856 or WO 2018 / 149857.

[0007] M. Schraub et al., European Polymer Journal 51 (2014) 21-27, describe the optical chemistry of 3-phenyl-coumarin-containing polymethacrylates.

[0008] The synthesis of azacoumarins is known from the literature, for example from R.B. Moffett, J. Org. Chem. 1970, 35(11), 3596-3600, D. Bonnetaud et al, J. Heterocycl. Chem. 1972, 9(1), 165-166D, F. Trecourt et al, J. Chem. Soc. Perkin Trans I, 1990, 2409-2415, Billeret et al, J. Heterocycl. Chem 1993, 30(3), 671-674, G. Brufola et al, Heterocycles, 1997, 45, 9, 1715-1721 and D. Wang et al, Org. Lett. 2017, 19, 984-987, as well as from the patent literature, for example from Chinese Patent No. 106810559.

[0009] The synthesis of pyranopyridones is known, for example, from OS Wolfbeis, Monatshefte fur Chemie, 1982, 113, 365-370.

[0010] US Pat. No. 4,103,256 describes a dye laser containing a laser dye solution of an azacoumarin compound.

[0011] Japanese Patent Publication Nos. 8301849, 8337583 and US Pat. No. 5,585,385 describe heterocyclic compounds having tachykinin receptor antagonist activity.

[0012] Patent Publication No. 2004203751 describes 6,6-heterobicyclic derivatives as corticotropin-releasing factor (hormone) CRF (CRH) antagonists useful for Alzheimer's disease and obesity.

[0013] Chinese Patent No. 106810560 describes a method for synthesizing azacoumarin derivatives and their application in antitumor drugs.

[0014] Chinese Patent No. 106810559 describes selective inhibitors of fibroblast growth factor receptors, which contain a nitrogen-containing heterocyclic six-membered ring, with a double bond-containing group attached to the bicycle via an N-phenyl-N group.

[0015] WO2007136125 and WO2007132948 describe compositions for inhibiting gene transcription in the extracellular matrix.

[0016] WO2007082178 describes prostaglandin reductase inhibitors.

[0017] WO2008094476 describes substituted pyrano[2,3-B]pyridine derivatives as cannabinoid-1 receptor modulators.

[0018] WO 2010049269, WO 2010049270, and WO 2011117195 describe substituted pyridines and their use as herbicides. WO 2011057942 describes substituted pyridines for use as pesticides in agriculture and veterinary medicine. WO 2012150550 describes aminopyranones as pesticidal compounds.

[0019] WO2018171688 describes compounds for the treatment and / or prevention of obesity and obesity-related disorders.

[0020] WO 2000008026 describes the synthesis of fungicidal fused bicyclic heterocycles.

[0021] US Patent No. 20070053831 describes a method for labeling structures such as β-amyloid plaques and neurofibrillary tangles in vivo or in vitro, which involves contacting brain tissue with certain azacoumarin compounds.

[0022] WO2009032754 describes compounds and methods useful as modulators of CB2 for treating or preventing disease states.

[0023] US Patent No. 20110021522 describes azacoumarin compounds and related derivatives and pharmaceutical compositions thereof as activators of procaspases 3, 6 and / or 7.

[0024] WO2013130689 describes compounds for treating spinal muscular atrophy.

[0025] WO2016146583 describes the synthesis of KV1.3 inhibitors and related starting materials.

[0026] However, there remains a need to provide alternative or improved ophthalmic devices, such as contact lenses or lenses, that are implanted by state-of-the-art cataract surgical procedures, and there remains a need to provide special compounds for the manufacture of ophthalmic devices, such as intraocular lenses, that are implanted by state-of-the-art cataract surgical procedures, particularly state-of-the-art microincision cataract surgical procedures. Summary of the Invention [Problem to be solved by the invention]

[0027] As a result, it is an object of the present application to provide alternative or improved ophthalmic devices and suitable compounds for the manufacture of such ophthalmic devices.

[0028] It is also an object of the present application to provide compounds, the optical properties of which can be altered, preferably by non-invasive techniques.

[0029] A further object of the present application is to provide an alternative compound or compounds that have advantages in combination with currently known compounds, preferably those suitable for ophthalmic devices.

[0030] An advantage of the monomers of formula (I) used in the preparation of ophthalmic devices according to the present invention is better handling due to their low melting point due to their use in compositions and / or polymers / copolymers. A further advantage is that the liquid to low melting monomers of formula (I) used in the preparation of ophthalmic devices according to the present invention allow for greater flexibility in the selection of initiators for heat-activated polymerization.

[0031] The advantages of the polymers or copolymers comprising polymerized monomers of formula (I) according to the present invention are good flexibility and low glass transition temperatures. The polymers or copolymers according to the present invention preferably exhibit significant polarizability or refractive index changes after irradiation, in part exhibiting higher starting refractive indices. The total refractive index change per mmol of photoactive chromophore is much higher compared to prior art materials. This allows for greater flexibility in adjusting the polarizability or refractive index of ophthalmic devices according to the present invention. Based on this advantage of the polymers or copolymers of the present invention, ophthalmic devices comprising such materials can be manufactured thinner than ophthalmic devices comprising prior art materials. [Means for solving the problem]

[0032] The inventors have now discovered that the above objectives may be achieved either individually or in any combination by the ophthalmic devices and compounds of the present application.

[0033] The present invention relates to an ophthalmic device, or a precursor article for producing an ophthalmic device, comprising at least one polymeric compound of formula (I):

[0034] [ka] During the ceremony, Divalent group

[0035] [ka] is selected from the group consisting of formula (B-1), formula (B-2), formula (B-3), formula (B-4) or formula (B-5),

[0036] [ka] asterisk * indicates the bond to the remainder of formula (I), Y1, Y2, Y3, and Y4 are each independently CR' or N, provided that only one of Y1, Y2, Y3, and Y4 is N, and the others are CR'; Y5 is O, S, or NR B and R B is independently selected in each occurrence from a linear or branched chain alkyl group having 1 to 10 carbon atoms, or a partially or fully fluorinated linear or branched chain alkyl group having 1 to 10 carbon atoms; X is O or S; Y0 is O or S; A1, A2, A3, and A4 are each independently N, CR″, or CY-R2-R1, provided that when m1 is 1, only one of A1, A2, A3, and A4 is N, and the others are CR″, provided that when m1 is 0, only one of A1, A2, A3, and A4 is N, and only one of A1, A2, A3, and A4 is CY-R2-R1, and the others are each independently CR″; or when m1 is 0, adjacent A1-A2, A2-A3, or A3-A4 are each independently -N(R2-R1)-C(=O)- or -C(=O)-N(R2-R1)-, and the remaining A3, A4, A1, and A2 are each independently CR''; Y's are, independently of one another, O, S, SO2 or a bond; m1 is 0 or 1, n1 is 4, n2 is 2, R' in each occurrence is independently selected from the group consisting of H, F, SF5, CN, SO2CF3, a straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkyl group having 1 to 20 carbon atoms, a non-halogenated, partially halogenated or fully halogenated cycloalkyl group having 3 to 6 carbon atoms, a straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkoxy group having 1 to 20 carbon atoms, and a straight or branched chain, non-halogenated, partially halogenated or fully halogenated thioalkyl group having 1 to 20 carbon atoms; R″ in each occurrence is independently selected from the group consisting of H, F, Cl, Br, CN, SO2CF3, straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkyl groups having 1 to 20 carbon atoms, non-halogenated, partially halogenated or fully halogenated cycloalkyl groups having 3 to 6 carbon atoms, straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkoxy groups having 1 to 20 carbon atoms, and straight or branched chain, non-halogenated and partially halogenated or fully halogenated thioalkyl groups having 1 to 20 carbon atoms; R1 is a trialkoxysilyl group or a dialkoxyalkylsilyl group in which the alkyl group and / or the alkoxy group are each independently linear or branched and have 1 to 6 carbon atoms, or a silyl group of formula (1), formula (2), or formula (3), or a polymerizable group of formula (4),

[0037] [ka] Here, alkyl, in each occurrence, independently means a straight or branched chain alkyl group having 1 to 6 carbon atoms; * " are, in each occurrence independently of each other, a linker, -R2-, -R2-Y or [Y-R2-] m1 indicates a bond to During the ceremony, X 11is selected from the group consisting of O, S, O-SO2, SO2-O, C(=O), OC(=O), C(=O)O, S(C=O), and (C=O)S; R5, R6, and R7, in each occurrence, are independently selected from the group consisting of H, F, linear or branched, non-fluorinated, partially or fully fluorinated alkyl groups having 1 to 20 carbon atoms, and aryl groups having 6 to 14 carbon atoms; c is 0 or 1; -R2- is -(C(R)2) o - or -(C(R)2) p -X8-(C(R)2) q -(X9) s -(C(R)2) r -(X 10 ) t -(C(R)2) u - and R in each occurrence is independently selected from the group consisting of H, F, a linear or branched chain alkyl group having 1 to 4 carbon atoms, or a linear or branched chain partially or fully fluorinated alkyl group having 1 to 4 carbon atoms; o is selected from the group consisting of 0 to 20; X8, X 9、 X 10 is independently in each occurrence O, S, SO, or NR; s and t are 0 or 1, p, q are independently selected in each occurrence from the group consisting of 1 to 10; r, u are independently selected in each occurrence from the group consisting of 0 to 10, wherein -(C(R)2) p -X8-(C(R)2) q -(X9) s -(C(R)2) r -(X 10 ) t -(C(R)2) u The total number of atoms is at most 20, R0 in each occurrence is independently selected from the group consisting of linear or branched alkyl groups having 1 to 4 carbon atoms, and linear or branched partially or fully fluorinated alkyl groups having 1 to 4 carbon atoms; R3 is H, F, Cl, Br, CN, or a linear or branched, non-halogenated, partially halogenated, or fully halogenated alkyl group having 1 to 20 carbon atoms; When m1 is 0, R4 is R'; When m1 is 1, R4 is R1.

[0038] The present invention further relates to a process for forming an ophthalmic device or a precursor article for manufacturing an ophthalmic device as described above or preferably below, the process comprising: - providing a composition comprising at least one compound of formula (I) as described above or preferably as described below, and / or an oligomer or polymer derived from a compound of formula (I) as described below or preferably as described below, but having at least one reactive group remaining for polymerization and optionally further monomers different from the compound of formula (I), and / or a crosslinker, and / or an ultraviolet absorber, and / or a radical initiator, - then forming an ophthalmic device or precursor article from the composition; Includes.

[0039] The present invention further relates to a process for modifying the optical properties of an ophthalmic device or a precursor article for manufacturing an ophthalmic device as described above or preferably below, said process comprising: - providing an ophthalmic device or precursor article by a process as described above or preferably below; - subsequently exposing the ophthalmic device or precursor article to radiation having a wavelength of at least 200 nm and at most 1500 nm; Includes.

[0040] The present invention further relates to an ophthalmic device or a precursor article for producing an ophthalmic device obtained by the process described above or, preferably, below, which alters the optical properties.

[0041] The present invention further relates to oligomers, polymers, or copolymers comprising at least one polymeric compound of formula (I), as described above or preferably below.

[0042] The present invention further relates to a composition for polymerization comprising at least one compound of formula (I) as described above or preferably below, and / or an oligomer or polymer derived from a compound of formula (I) as described above or preferably below but having at least one reactive group remaining for polymerization, and / or a crosslinker, and / or an UV absorber, and / or a radical initiator, and optionally further monomers different from the compound of formula (I).

[0043] The present invention further relates to compounds of formula (I):

[0044] [ka] During the ceremony, Divalent group

[0045] [ka] is selected from the group of formula (B-1), formula (B-2), formula (B-3), formula (B-4) or formula (B-5),

[0046] [ka] asterisk * indicates the bond to the remainder of formula (I), Y1, Y2, Y3, and Y4 are each independently CR' or N, provided that only one of Y1, Y2, Y3, and Y4 is N, and the others are CR'; Y5 is O, S, or NR B and R B is independently selected in each occurrence from a linear or branched chain alkyl group having 1 to 10 carbon atoms, or a partially or fully fluorinated linear or branched chain alkyl group having 1 to 10 carbon atoms; A1, A2, A3, and A4 are each independently N, CR″, or CY-R2-R1, provided that when m1 is 1, only one of A1, A2, and A3 is N, and the others and A4 are CR″, provided that when m1 is 0, only one of A1, A2, and A3 is N, and only one of A1, A2, A3, and A4 is CY-R2-R1, and the others are each independently CR″; or when m1 is 0, adjacent A1-A2, A2-A3, or A3-A4 are each independently -N(R2-R1)-C(=O)- or -C(=O)-N(R2-R1)-, and the remaining A3, A4, A1, and A2 are each independently CR''; Y's are, independently of one another, O, S, SO2 or a bond; m1 is 0 or 1, n1 is 4, n2 is 2, R' in each occurrence is independently selected from the group consisting of H, F, SF5, CN, SO2CF3, a straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkyl group having 1 to 20 carbon atoms, a non-halogenated, partially halogenated or fully halogenated cycloalkyl group having 3 to 6 carbon atoms, a straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkoxy group having 1 to 20 carbon atoms, and a straight or branched chain, non-halogenated, partially halogenated or fully halogenated thioalkyl group having 1 to 20 carbon atoms; R″ in each occurrence is independently selected from the group consisting of H, F, Cl, Br, CN, SO2CF3, straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkyl groups having 1 to 20 carbon atoms, non-halogenated, partially halogenated or fully halogenated cycloalkyl groups having 3 to 6 carbon atoms, straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkoxy groups having 1 to 20 carbon atoms, and straight or branched chain, non-halogenated and partially halogenated or fully halogenated thioalkyl groups having 1 to 20 carbon atoms; R1 is a trialkoxysilyl group or a dialkoxyalkylsilyl group in which the alkyl group and / or the alkoxy group are each independently linear or branched and have 1 to 6 carbon atoms, or a silyl group of formula (1), formula (2), or formula (3), or a polymerizable group of formula (4),

[0047] [ka] Here, alkyl, in each occurrence, independently means a straight or branched chain alkyl group having 1 to 6 carbon atoms; * " are, in each occurrence independently of each other, a linker, -R2-, -R2-Y or [Y-R2-] m1 indicates a bond to During the ceremony, X 11 is selected from the group consisting of O, S, O-SO2, SO2-O, C(=O), OC(=O), C(=O)O, S(C=O), and (C=O)S; R5, R6, and R7, in each occurrence, are independently selected from the group consisting of H, F, linear or branched, non-fluorinated, partially or fully fluorinated alkyl groups having 1 to 20 carbon atoms, and aryl groups having 6 to 14 carbon atoms; c is 0 or 1; -R2- is -(C(R)2) o - or -(C(R)2) p -X8-(C(R)2) q -(X9) s -(C(R)2)r -(X 10 ) t -(C(R)2) u - and R in each occurrence is independently selected from the group consisting of H, F, a linear or branched chain alkyl group having 1 to 4 carbon atoms, or a linear or branched chain partially or fully fluorinated alkyl group having 1 to 4 carbon atoms; o is 0 to 20, X8, X 9、 X 10 is independently in each occurrence O, S, SO, or NR; s and t are 0 or 1, p and q are independently selected in each occurrence from the group consisting of 1 to 10; r and u are independently selected in each occurrence from the group consisting of 0 to 10, wherein -(C(R)2) p -X8-(C(R)2) q -(X9) s -(C(R)2) r -(X 10 ) t -(C(R)2) u The total number of atoms is at most 20, R0 in each occurrence is independently selected from the group consisting of linear or branched alkyl groups having 1 to 4 carbon atoms, and linear or branched partially or fully fluorinated alkyl groups having 1 to 4 carbon atoms; R3 is H, F, Cl, Br, CN, or a linear or branched, non-halogenated, partially halogenated, or fully halogenated alkyl group having 1 to 20 carbon atoms; When m1 is 0, R4 is R'; when m1 is 1, R4 is R1; However, when m1 is 0, Y is O or S, and A2 is CY-R2-R1, Divalent group

[0048] [ka] is at the 3-position and is selected from formula (B-3) and formula (B-4), Y4 in formula (B-3) is N, Y3 in formula (B-4) is N, and c is 1; However, when m1 is 1, A2 is CR″, and R″ is a linear or branched, non-halogenated, partially halogenated or fully halogenated alkoxy group having 1 to 20 carbon atoms, and a linear or branched, non-halogenated, partially halogenated or fully halogenated thioalkyl group having 1 to 20 carbon atoms, Divalent group

[0049] [ka] is at the 3-position and is selected from formula (B-3), wherein Y2 in formula (B-3) is CR', R' is H, Y4 in formula (B-3) is N, Y is a bond, O or S, and c is 1; However, when m1 is 1, Y is a bond, c is 0, and R3 is Cl, Divalent group

[0050] [ka] is in third place, o is 5-20, However, when m1 is 0, Y is a bond or O, c is 0, and R3 is Cl, Divalent group

[0051] [ka] is in third place, o is 7-20, However, when m1 is 0, X is O, Y0 is O, and Y is a bond, c is 1 and X 11 are O, S, O-SO2, SO2-O, OC(=O), C(=O)O, S(C=O) and (C=O)S, However, when m1 is 1, X is O, and Y0 is O, o is 5 to 20; However, when m1 is 1, c is 0, and Y is a bond or O, Divalent group

[0052] [ka] is in third place, o is 11-20, However, when m1 is 1, A1 or A3 is N, Y is a bond, and c is 0, Divalent group

[0053] [ka] is in third place, o is 7-20, However, when m1 is 0, X is O, Y0 is O, Y is O or S, c is 0, A2 is CY-R2-R1, A3 is Br, and A1 is N, Divalent group

[0054] [ka] is at the 4-position and is selected from formula (B-1), formula (B-3), and formula (B-4), and o is 2 to 20. [Brief explanation of the drawings]

[0055] [Figure 1] 1 is a graph showing the relationship between refractive index change Δn and amount of mmol photoactive chromophore per total amount of formulation in grams for the compounds listed in Table 5. DETAILED DESCRIPTION OF THE INVENTION

[0056] The compounds of formula (I) as described above or preferably below may preferably be used as monomers for the preparation of precursor articles such as blanks which may be converted into ophthalmic devices such as ocular implants or in particular intraocular lenses, or may preferably be used in the preparation of ophthalmic devices as described above or preferably below.

[0057] The compounds of formula (I) comprising any monomeric unit according to the present invention and all preferred embodiments of the compounds of formula (I) include all stereoisomers or racemic mixtures.

[0058] The compounds of formula (I) offer several advantages over prior art materials for the preparation of ophthalmic devices or precursor articles for making ophthalmic devices, as discussed above. Furthermore, the addition of a nitrogen atom to the left aromatic moiety of the central chromophore of compounds of formula (I) or oligomers, polymers, and copolymers comprising polymerized compounds of formula (I) significantly affects the optical properties over prior art compounds, as discussed above.

[0059] Polymers that are foldable at room temperature generally have a glass transition temperature (T) below room temperature (approximately 21°C). g ) at which they are readily deformable without causing physical damage to the polymer, for example by inducing creep, stress, or cracking. For polymers in intraocular lenses, a T of 15°C or less is required. g is preferred.

[0060] Polymers used in ophthalmic device manufacturing, preferably intraocular lens manufacturing, preferably have a relatively high refractive index, which allows for the creation of thinner ophthalmic devices, such as intraocular lenses. Preferably, polymers used in ophthalmic devices, preferably intraocular lenses, have a refractive index greater than about 1.5, and currently most preferably greater than about 1.55.

[0061] In the description of this invention, an asterisk (" * "), when used, indicates a bond to an adjacent unit or group, or in the case of a polymer, to an adjacent repeat unit or any other group, whenever not otherwise defined.

[0062] A straight or branched alkyl group having 1 to 10 carbon atoms denotes an alkyl group having 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms, such as methyl, ethyl, isopropyl, n-propyl, isobutyl, n-butyl, tert-butyl, n-pentyl, 1-, 2- or 3-methylbutyl, 1,1-, 1,2- or 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, n-heptyl, n-octyl, ethylhexyl, n-nonyl or n-decyl. Straight or branched chain alkyl groups having 1 to 20 carbon atoms include all examples of straight or branched chain alkyl groups having 1 to 10 carbon atoms, including any alkyl groups having 11, 12, 13, 14, 15, 16, 17, 18, 19, and 20 carbon atoms, such as n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, and n-eicosyl.

[0063] The term partially halogenated alkyl group indicates that at least one H atom of the alkyl group is replaced with F, Cl, Br, or I. Preferably, the alkyl group is partially fluorinated, meaning that at least one H atom of the alkyl group is replaced with F. A preferred partially halogenated alkyl group is CHCF.

[0064] The term fully halogenated alkyl group indicates that all H atoms of the alkyl group have been replaced with F, Cl, Br, and / or I. Preferably, the alkyl group is fully fluorinated, meaning that all H atoms of the alkyl group have been replaced with F. Preferred fully fluorinated alkyl groups are trifluoromethyl or pentafluoroethyl.

[0065] The term halogenated or preferably fluorinated additionally corresponds to other groups such as halogenated cycloalkyl groups, halogenated alkoxy groups, or halogenated thioalkyl groups.

[0066] Cycloalkyl groups having 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl, which may be partially or fully halogenated or fluorinated as described above. Preferably, the cycloalkyl group is cyclopropyl.

[0067] A straight or branched chain alkoxy group having 1 to 20 carbon atoms is an O-alkyl group having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms, such as methoxy, ethoxy, iso-propoxy, n-propoxy, iso-butoxy, n-butoxy, tert-butoxy, n-pentyloxy, 1-, 2- or 3-methylbutyloxy, 1,1-, 1,2- or 2,2-dimethylpropoxy, 1-ethylpropoxy, n-hexyloxy, alkoxy, n-heptyloxy, n-octyloxy, ethylhexyloxy, n-nonyloxy, n-decyloxy, n-undecyloxy, n-dodecyloxy, n-tridecyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy, n-nonadecyloxy, and n-eicosyloxy, which may be partially or fully halogenated, or preferably partially or fully fluorinated. A preferred fully fluorinated alkoxy group is trifluoromethoxy.

[0068] A straight or branched chain thioalkyl group having 1 to 20 carbon atoms is an S-alkyl group having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms, such as thiomethyl, 1-thioethyl, 1-thio-isopropyl, 1-thio-n-propanol, 1-thio-isobutyl, 1-thio-n-butyl, 1-thio-tert-butyl, 1-thio-n-pentyl, 1-thio-1-, -2- or -3-methylbutyl, 1-thio-1,1-, -1,2- or -2,2-dimethylpropyl, 1-thio-1-ethylpropyl, 1-thio-n-pentyl, 1-thio-n-isopropyl, 1-thio-n-butyl, 1-thio-n-tert-butyl, 1-thio-n-pentyl, 1-thio-n-isopropyl ... The thioether groups include 1-thio-n-hexyl, 1-thio-n-heptyl, 1-thio-n-octyl, 1-thio-ethylhexyl, 1-thio-n-nonyl, 1-thio-n-decyl, 1-thio-n-undecyl, 1-thio-n-dodecyl, 1-thio-n-tridecyl, 1-thio-n-tetradecyl, 1-thio-n-pentadecyl, 1-thio-n-hexadecyl, 1-thio-n-heptadecyl, 1-thio-n-octadecyl, 1-thio-n-nonadecyl, and 1-thio-n-eicosyl, which may be partially or fully halogenated, or preferably partially or fully fluorinated. A preferred fully fluorinated thioether group is trifluoromethyl thioether.

[0069] Preferred alkyl and alkoxy radicals have 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms.

[0070] Aryl groups in the context of the present invention contain 6 to 40 ring atoms and heteroaryl groups, in the context of the present invention, contain 5 to 40 ring atoms, including at least one heteroatom. The heteroatoms are preferably selected from N, O and / or S. An aryl or heteroaryl group is understood herein to mean either a simple aromatic cycle, i.e., phenyl, or a simple heteroaromatic cycle, such as pyridinyl, pyrimidinyl, thiophenyl, etc., or a fused (annelated) aryl or heteroaryl group, such as naphthyl, anthracenyl, phenanthrenyl, quinolinyl, or isoquinolinyl.

[0071] The aryl or heteroaryl group is preferably benzene, naphthalene, anthracene, phenanthrene, pyrene, benzanthracene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-indenocarbazole, cis- or trans-indocarbazole, truxene, isotruxene, spirotoxene, benzopyrene, benzopyrene, benzophenone ... Truxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthridine, pyrimidine azole, pyrazine imidazole, quinoxaline imidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, hexaazatriphenylene, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1,5-diazaanthracene, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazapyrene Benzene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorubine, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,It is derived from 3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine and benzothiadiazole.

[0072] A polymerizable group is a group that can undergo or undergo polymerization, thus forming an oligomer or polymer.

[0073] Polymerization is the process of taking individual monomers and chaining them together to make longer units. These longer units are called polymers. The compounds of formula (I) described above, and preferably below, are suitable monomers for preparing ophthalmic devices or precursor articles for making ophthalmic devices.

[0074] Within the scope of the present invention, the polymerizable group R1, when oligomerized or polymerized, results in the formation of or is part of the backbone of an oligomer, polymer, or copolymer comprising the polymerized compound of formula (I). Suitable polymerizable groups are: a trialkoxysilyl group or a dialkoxyalkylsilyl group, each of which is a straight or branched chain alkyl group and / or alkoxy group, each of which independently has 1 to 6 carbon atoms, or a silyl group of formula (1), formula (2), or formula (3), or a polymerizable group of formula (4),

[0075] [ka] Here, alkyl, in each occurrence, independently means a straight or branched chain alkyl group having 1 to 6 carbon atoms; * " are, in each occurrence independently of each other, a linker, -R2-, -R2-Y or [Y-R2-] m1 indicates a bond to During the ceremony, X 11 is selected from the group consisting of O, S, O-SO2, SO2-O, C(=O), OC(=O), C(=O)O, S(C=O), and (C=O)S; R5, R6, and R7, in each occurrence, are independently selected from the group consisting of H, F, linear or branched, non-fluorinated, partially or fully fluorinated alkyl groups having 1 to 20 carbon atoms, and aryl groups having 6 to 14 carbon atoms; c is defined to be 0 or 1.

[0076] Particularly preferred polymerizable groups are described below:Particularly preferred polymerizable groups are described below.

[0077] Aryl having 6 to 14 carbon atoms is preferably an aryl group selected from the group consisting of phenyl, naphthyl or anthryl, particularly preferably phenyl.

[0078] In one preferred embodiment, compounds of formula (I) that act as monomers for the preparation of the aforementioned ophthalmic devices or precursor articles for making ophthalmic devices, or as monomers for the preparation of oligomers, polymers or copolymers according to the invention, or as compounds according to the invention, contain a polymerizable group R1 attached to the photoactive ring system via -R2- and Y. This is the case for compounds of formula (I) where m1 is 0, which compounds can therefore be described by formula (I').

[0079] Accordingly, the present invention further relates to an ophthalmic device or a precursor article for producing an ophthalmic device, comprising at least one polymeric compound of formula (I'),

[0080] [ka] In the formula, R1, -R2-, Y, R3, X, Y0, R', and R'' are

[0081] [ka] has the meaning as stated above or preferably as stated above or below, A1, A2, A3, and A4 are each independently N, CR″, or CY-R2-R1, provided that only one of A1, A2, A3, and A4 is N, only one of A1, A2, A3, and A4 is CY-R2-R1, and the others are each independently CR″; or Adjacent pairs of A1-A2, A2-A3, or A3-A4 are each independently -N(R2-R1)-C(=O)- or -C(=O)-N(R2-R1)-, and the remaining pairs of A3, A4, A1, and A2 are each independently CR'' and R4 is R'.

[0082] Thus, the present invention further relates to compounds of formula (I) in which m1 is 0, which compounds can preferably be described according to formula (I'):

[0083] [ka] In the formula, R1, -R2-, Y, R3, X, Y0, R', and R'' are

[0084] [ka] has the meaning as stated above or preferably as stated above or below, A1, A2, A3, and A4 are each independently N, CR″, or CY-R2-R1, provided that only one of A1, A2, and A3 is N, only one of A1, A2, A3, and A4 is CY-R2-R1, and the others are each independently CR″; or, adjacent A1-A2, A2-A3, or A3-A4 are each independently -N(R2-R1)-C(=O)- or -C(=O)-N(R2-R1)-, and the remaining A3, A4, A1, and A2 are each independently CR'' and R4 is R'; However, when Y is O or S and A2 is CY-R2-R1, Divalent group

[0085] [ka] is at the 3-position and is selected from formula (B-3) and formula (B-4), Y4 in formula (B-3) is N, Y3 in formula (B-4) is N, and c is 1; However, when Y is a bond or O, c is 0, and R3 is Cl, Divalent group

[0086] [ka] is in third place, o is 7-20, However, when X is O, Y is O, Y is a bond, and c is 1, then X 11 are O, S, O-SO2, SO2-O, OC(=O), C(=O)O, S(C=O) and (C=O)S, provided that when X is O, Y is O, Y is O or S, c is 0, A is CY-R-R, A is Br, and A is N, then: Divalent group

[0087] [ka] is at the 4-position and is selected from formula (B-1), formula (B-3), and formula (B-4), and o is 2 to 20.

[0088] In formula (I) or formula (I'), the position of the substituent R1-R2-Y or R1-R2- is determined by the positions of A1, A2, A3, A4, A1-A2, A2-A3 and A3-A4.

[0089] In the compounds of formula (I'-a), the substituent A1 is CY-R2-R1, which is at the 8-position of the photoactive chromophore, and A2, A3 and A4 have the meanings described above for the compounds of formula (I) or formula (I'). In the compounds of formula (I'-a), A2 is preferably N.

[0090] In the compounds of formula (I'-b), the substituent A2 is CY-R2-R1, which is at the 7-position of the photoactive chromophore, and A1, A3 and A4 have the meanings described above for the compounds of formula (I) or formula (I'). In the compounds of formula (I'-b), A1 or A3 is preferably N.

[0091] In the compounds of formula (I'-c), the substituent A3 is CY-R2-R1, which is at the 6-position of the photoactive chromophore, and A1, A2 and A4 have the meanings described above for the compounds of formula (I) or formula (I'). In the compounds of formula (I'-c), A1 or A2 is preferably N.

[0092] In the compounds of formula (I'-d), the substituent A4 is CY-R2-R1, which is at the 5-position of the photoactive chromophore, and A1, A2 and A3 have the meanings described above for the compounds of formula (I) or formula (I'). In the compounds of formula (I'-d), A1 or A2 is preferably N.

[0093] In compounds of formula (I'-e), the substituents A1-A2 are -N(R2-R1)-CO-, and A3 and A4 have the meanings described above for compounds of formula (I) or formula (I').

[0094] In compounds of formula (I'-f), the substituents A1-A2 are -CO-N(R2-R1), and A3 and A4 have the meanings described above for compounds of formula (I) or formula (I').

[0095] In compounds of formula (I'-g), the substituents A2-A3 are -N(R2-R1)-CO-, and A1 and A4 have the meanings described above for compounds of formula (I) or formula (I').

[0096] In compounds of formula (I'-h), the substituents A2-A3 are -CO-N(R2-R1), and A1 and A4 have the meanings described above for compounds of formula (I) or formula (I').

[0097] In compounds of formula (I'-i), the substituents A3-A4 are -N(R2-R1)-CO-, where A1 and A2 have the meanings described above for compounds of formula (I) or formula (I').

[0098] The present invention therefore further relates to an ophthalmic device or a precursor article for producing an ophthalmic device comprising at least one polymerized compound of formula (I), wherein m1 is 0, which can preferably be described according to formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h) and formula (I'-i),

[0099] [ka]

[0100] [ka] In the formula, R1, -R2-, X, Y0, Y, A1, A2, A3, A4, R3, R4 and

[0101] [ka] has the meaning as defined above or preferably as defined above or below.

[0102] Accordingly, the present invention relates to compounds of formula (I), wherein n is 1 and m is 0, and which may be described preferably according to formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h), and formula (I'-i), as previously described, wherein R, -R-, X, Y, Y, A, A, A, A, R, R and

[0103] [ka] has the meaning as set forth above, or preferably as set forth above or below, and must be used as disclosed, subject to the provisos given.

[0104] Preferred positions of R1-R2-YC or R1-R2-N are, for example, the 8- and / or 7-positions of the photoactive chromophore visualized in formula (I'-a), formula (I'-b), formula (I'-e), formula (I'-g) and formula (I'-f).

[0105] In another preferred embodiment of the present invention, the compound of formula (I) which serves as a monomer for the preparation of an ophthalmic device or a precursor article for the manufacture of an ophthalmic device as described above, or as a monomer for the preparation of an oligomer, polymer or copolymer according to the present invention or as a compound according to the present invention as described above, comprises a polymerizable group R1 linked via -R2- and Y to a divalent group attached to a photoactive chromophore. This is the case for compounds of formula (I) where m1 is 1, which compound can therefore be described by formula (I'').

[0106] Thus, the present invention further relates to an ophthalmic device or a precursor article for producing an ophthalmic device, comprising at least one polymeric compound of formula (I″),

[0107] [ka] In the formula, R1, -R2-, Y, R3, X, Y0, R', and R'' are

[0108] [ka] has the meaning as stated above or preferably as stated above or below, A1, A2, A3, and A4 are each independently N or CR'', provided that only one of A1, A2, A3, and A4 is N, and the others are CR''.

[0109] The present invention therefore further relates to compounds of formula (I) in which m1 is 1, which can be preferably described according to formula (I″):

[0110] [ka] In the formula, R1, -R2-, Y, R3, X, Y0, R', and R'' are

[0111] [ka] has the meaning as stated above or preferably as stated above or below, A1, A2, A3, and A4 are each independently N or CR″, provided that only one of A1, A2, and A3 is N, and the others and Ar4 are CR″; However, when A2 is CR″ and R″ is a linear or branched, non-halogenated, partially halogenated or fully halogenated alkoxy group having 1 to 20 carbon atoms, and a linear or branched, non-halogenated, partially halogenated or fully halogenated thioalkyl group having 1 to 20 carbon atoms, Divalent group

[0112] [ka] is at the 3-position and is selected from formula (B-3), wherein Y2 in formula (B-3) is CR', R' is H, Y4 in formula (B-3) is N, Y is a bond, O or S, and c is 1; However, when Y is a bond, c is 0, and R3 is Cl, Divalent group

[0113] [ka] is in third place, o is 5-20, However, when X is O and Y0 is O, o is 5 to 20; However, when c is 0 and Y is a bond or O, Divalent group

[0114] [ka] is in third place, o is 11-20, However, when A1 or A3 is N, Y is a bond, and c is 0, Divalent group

[0115] [ka] is in third place, and o is 7-20.

[0116] As described above for ophthalmic devices, precursor articles for making ophthalmic devices, compounds of Formula (I), Formula (I'), Formula (I'-a), Formula (I'-b), Formula (I'-c), Formula (I'-d), Formula (I'-e), Formula (I'-f), Formula (I'-g), Formula (I'-h), Formula (I'-i) or Formula (I''), and any oligomers, polymers or copolymers derived therefrom according to the present invention, the substituent R'' may, independently in each occurrence, be H, F, Cl, Br, CN, SOCF, a compound having 1 to 1 carbon atoms, a linear or branched, non-halogenated, partially halogenated or fully halogenated alkyl group having from 20 carbon atoms, a non-halogenated, partially halogenated or fully halogenated cycloalkyl group having from 3 to 6 carbon atoms, a linear or branched, non-halogenated, partially halogenated or fully halogenated alkoxy group having from 1 to 20 carbon atoms, and a linear or branched, non-halogenated and partially halogenated or fully halogenated thioalkyl group having from 1 to 20 carbon atoms.

[0117] R" is independently in each occurrence preferably H, F, Cl, Br, CN, or a straight or branched chain non-halogenated, partially halogenated, or fully halogenated alkyl group having 1 to 20 carbon atoms. R" is particularly preferably H.

[0118] As described above for ophthalmic devices, precursor articles for making ophthalmic devices, compounds of formula (I), formula (I'), formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), and formula (I'-h), formula (I'-i) or formula (I'') and any oligomers, polymers or copolymers derived therefrom according to the present invention,

[0119] [ka] is selected from the group of formula (B-1), formula (B-2), formula (B-3), formula (B-4) or formula (B-5),

[0120] [ka] asterisk * represents a linkage to the remainder of formula (I), formula (I'), formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h), formula (I'-i) or formula (I''); Y1, Y2, Y3, and Y4 are each independently CR' or N, provided that only one of Y1, Y2, Y3, and Y4 is N, and the others are CR'; Y5 is O, S, or NR B and R B R is independently selected in each occurrence from a linear or branched chain alkyl group having 1 to 10 carbon atoms, or a linear or branched chain partially or fully fluorinated alkyl group having 1 to 10 carbon atoms. B is preferably a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched partially or fully fluorinated alkyl group having 1 to 4 carbon atoms.

[0121] Within the group of formula (B-5), Y5 is preferably O or S.

[0122] In one embodiment of the present invention, the divalent group

[0123] [ka] is preferably a group of formula (B-1) to formula (B-4).

[0124] In one embodiment of the present invention, the divalent group

[0125] [ka] is preferably a group of formula (B-1).

[0126] As described above for an ophthalmic device, a precursor article for making an ophthalmic device, a compound of Formula (I), Formula (I'), Formula (I'-a), Formula (I'-b), Formula (I'-c), Formula (I'-d), Formula (I'-e), Formula (I'-f), Formula (I'-g), Formula (I'-h), Formula (I'-i) or Formula (I''), and any oligomer, polymer or copolymer derived therefrom according to the present invention or in groups (B-1) through (B-5), the substituent R' is independently in each occurrence H, F, SF, CN, SO2C F3 is selected from the group consisting of a straight-chain or branched-chain, non-halogenated, partially halogenated or fully halogenated alkyl group having 1 to 20 carbon atoms, a non-halogenated, partially halogenated or fully halogenated cycloalkyl group having 3 to 6 carbon atoms, a straight-chain or branched-chain, non-halogenated, partially halogenated or fully halogenated alkoxy group having 1 to 20 carbon atoms, and a straight-chain or branched-chain, non-halogenated, partially halogenated or fully halogenated thioalkyl group having 1 to 20 carbon atoms.

[0127] R' is independently in each occurrence preferably H, F, SF, CN, SOCF, a straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkyl group having 1 to 10 carbon atoms, a non-halogenated, partially halogenated or fully halogenated cycloalkyl group having 3 to 6 carbon atoms, a straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkoxy group having 1 to 10 carbon atoms, and a straight or branched chain, non-halogenated, partially halogenated or fully halogenated thioalkyl group having 1 to 10 carbon atoms.

[0128] In one embodiment of the present invention, preferably all R' are H.

[0129] In one embodiment of the present invention, preferably one R' is different from H and the other substituent R' is selected from the list as above.

[0130] In one embodiment of the present invention, preferably two R' are different from H and the other substituent R' is selected from the list as above.

[0131] R', independently of one another, are particularly preferably selected from the group consisting of F, CN, SO2CF3, SF5, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl, methoxy, ethoxy, propoxy, trifluoromethoxy, pentafluoroethoxy, thiomethyl and thioethyl.

[0132] R', independently of one another, are particularly preferably selected from the group consisting of F, ethyl, n-pentyl, trifluoromethyl, methoxy and trifluoromethoxy.

[0133] With regard to the compounds according to the invention, the stated provisos must be taken into account for the definition of R'.

[0134] As described above for the ophthalmic device, the precursor article for producing the ophthalmic device, the compound of Formula (I), Formula (I'), Formula (I'-a), Formula (I'-b), Formula (I'-c), Formula (I'-d), Formula (I'-e), Formula (I'-f), Formula (I'-g), Formula (I'-h), Formula (I'-i), or Formula (I''), and any oligomer, polymer, or copolymer derived therefrom according to the present invention, R3 is H, F, Cl, Br, CN, or a linear or branched, non-halogenated, partially halogenated, or fully halogenated alkyl group having 1 to 20 carbon atoms. Preferably, R3 is H, F, or a linear or branched, non-halogenated, partially halogenated, or fully halogenated alkyl group having 1 to 10 carbon atoms. Particularly preferably, R3 is H.

[0135] As described above for the ophthalmic device, the precursor article for producing an ophthalmic device, the compound of Formula (I'), Formula (I'-a), Formula (I'-b), Formula (I'-c), Formula (I'-d), Formula (I'-e), Formula (I'-f), Formula (I'-g), Formula (I'-h), or Formula (I'-i) and any oligomer, polymer, or copolymer derived therefrom according to the present invention, R4 is R', and R' is as defined above or preferably has the meaning as defined above.

[0136] As described above for ophthalmic devices, precursor articles for making ophthalmic devices, compounds of Formula (I), Formula (I'), Formula (I'-a), Formula (I'-b), Formula (I'-c), Formula (I'-d), Formula (I'-e), Formula (I'-f), Formula (I'-g), and Formula (I'-h), Formula (I'-i) or Formula (I'') and any oligomers, polymers or copolymers derived therefrom according to the present invention, X is O or S, preferably O.

[0137] As described above for ophthalmic devices, precursor articles for making ophthalmic devices, compounds of Formula (I), Formula (I'), Formula (I'-a), Formula (I'-b), Formula (I'-c), Formula (I'-d), Formula (I'-e), Formula (I'-f), Formula (I'-g), Formula (I'-h), Formula (I'-i) or Formula (I'') and any oligomers, polymers or copolymers derived therefrom according to the present invention, Y is O or S, preferably O.

[0138] The present invention further relates to an ophthalmic device or a precursor article for producing an ophthalmic device comprising at least one polymerized compound of Formula (I), Formula (I'), Formula (I'-a), Formula (I'-b), Formula (I'-c), Formula (I'-d), Formula (I'-e), Formula (I'-f), Formula (I'-g), Formula (I'-h), Formula (I'-i) or Formula (I'') as defined above, or preferably as defined above, wherein X is O and Y is O.

[0139] In these embodiments of the invention, when m1 is 0 and R4 is R', the substitution pattern of the (B-1) group is preferably selected from (S-1) to (S-12):

[0140] [ka] wherein R' independently of one another has the meaning described above or preferably described below. Preferred substitution patterns are (S-1), (S-7), (S-10), (S-11) and (S-12). Particularly preferred substitution patterns are (S-7) and / or (S-10) and / or (S-12). A very particularly preferred substitution pattern is (S-7). A very particularly preferred substitution pattern is (S-10). A very particularly preferred substitution pattern is (S-12).

[0141] As described above, the substituent R4 corresponds to R1 when m1 is 1 in formula (I) or formula (I″), and R′ in the divalent groups of formulas (B-1) to (B-5) has the meaning described above, or a preferred or particularly preferred meaning described above.

[0142] In this embodiment where R4 is R1 and R1 is linked to a divalent radical of Formula (B-1) through Formula (B-4) via -R2-Y-, such R1-R2-Y- group is preferably in the ortho, meta, or para position relative to the bond of the divalent radical linked to the remainder of Formula (I) or Formula (I''). In this embodiment where R4 is R1 and R1 is linked to a divalent radical via -R2-Y-, such R1-R2-Y- group is particularly preferably in the ortho or para position relative to the bond of the divalent radical of Formula (B-1), Formula (B-2), or Formula (B-4) linked to the remainder of Formula (I) or Formula (I''). In this embodiment where R4 is R1 and R1 is linked to a divalent radical via -R2-Y-, such R1-R2-Y- group is very particularly preferably in the para position relative to the bond of the divalent radical of formula (B-1) or formula (B-2) linked to the remainder of formula (I) or formula (I'').

[0143] Accordingly, the present invention further relates to an ophthalmic device or a precursor article for producing an ophthalmic device comprising a polymeric compound of formula (I) or formula (I″), wherein R4 is R1, R′ has the meaning as defined above or preferably as defined below, and R1 is bonded to a divalent radical via —R2-Y—, such R1-R2-Y— group being in the ortho or para position relative to the bond of the divalent radical of formula (B-1), formula (B-2) and formula (B-4) to the remainder of formula (I) or formula (I″).

[0144] a divalent group as described above or preferably as described above

[0145] [ka] The preferred location of is at the 3-position of the photoactive chromophore.

[0146] The following formula is for a compound of formula (I) read as formula (I#), R3 and a divalent group

[0147] [ka] Summarizing the preferred positions of

[0148] [ka] In the formula, R1, -R2-, X, Y0, Y, R3, R4, m1,

[0149] [ka] A1, A2, A3 and A4 have the meanings as described above or preferably as described above or below. Such compounds according to formula (I#) preferably serve as monomers of formula (I) for the preparation of the aforementioned ophthalmic devices or precursor articles for producing ophthalmic devices, or for the preparation of oligomers, polymers or copolymers according to the invention.

[0150] According to the present invention, the compounds of formula (I), (I#), (I'), (I'-a), (I'-b), (I'-c), (I'-d), (I'-e), (I'-f), (I'-g), (I'-h), (I'-i) and (I'') having the substituents as described above or preferably as described above, have a polymerizable group as described above or preferably as described above or below and have at least one linking element Y-R2 or -R2-.

[0151] According to the present invention, Y is independently, at each occurrence, O, S, O=S=O or a bond.

[0152] According to the present invention, the linking element -R2- is -(C(R)2) o - or -(C(R)2) p -X8-(C(R)2) q -(X9) s -(C(R)2) r -(X 10 ) t -(C(R)2) u-, R is independently in each occurrence selected from the group consisting of H, F, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched partially or fully fluorinated alkyl group having 1 to 4 carbon atoms, o is selected from the group consisting of 1 to 20, X8, and X9, and X 10 is, in each occurrence, O, S, SO, or NR; s and t are, independently in each occurrence, 0 or 1; p and q are, in each occurrence, independently selected from the group consisting of 1 to 10; r and u are, in each occurrence, independently selected from the group consisting of 0 to 10; -(C(R)) p -X8-(C(R)2) q -(X9) s -(C(R)2) r -(X 10 ) t -(C(R)2) u The total number of atoms is up to 20. R in NR is independently at each occurrence selected from the group consisting of linear or branched alkyl groups having 1 to 4 carbon atoms and linear or branched partially or fully fluorinated alkyl groups having 1 to 4 carbon atoms. R is independently at each occurrence preferably methyl, ethyl, or trifluoromethyl. R is particularly preferably independently at each occurrence methyl.

[0153] According to the present invention, R, in each occurrence, is independently selected from the group consisting of H, F, a linear or branched alkyl group having 1 to 8 carbon atoms, or a linear or branched partially or fully fluorinated alkyl group having 1 to 4 carbon atoms. It is particularly preferred that R is, independently in each occurrence, H, F, methyl or ethyl. R is very particularly preferably H.

[0154] In another preferred embodiment of the present invention, o is preferably selected from the group consisting of 7, 8, 9, 10, 11, 12, 13 and 14 in the compounds of formula (I), (I#), (I'), (I'-a), (I'-b), (I'-c), (I'-d), (I'-e), (I'-f), (I'-g), (I'-h), (I'-i) and (I''), which act as a monomer for the preparation of an ophthalmic device or a precursor article for producing an ophthalmic device as described above, or for the preparation of an oligomer, polymer or copolymer according to the present invention or within the compound according to the present invention. Preferably, o is selected from the group consisting of 5, 6, 7, 8, 9, 10, 11, 12 and 13. Particularly preferably, o is selected from the group consisting of 8, 9, 10, 11 and 12. With regard to the compounds according to the invention, the stated provisos must be taken into account for the definition of o.

[0155] In another preferred embodiment of the present invention, s, t, X8, X9, X in the compounds of formula (I), formula (I#), formula (I'), formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h), formula (I'-i) and formula (I'') 10 , p, q, r and u act as monomers for the preparation of an ophthalmic device or a precursor article for producing an ophthalmic device as described above, or for the preparation of an oligomer, polymer or copolymer according to the invention or within a compound according to the invention, and have the following preferred meanings: Preferably, s is 1. Preferably, s is 0. Preferably, t is 0 or 1. Preferably, s and t are 0.

[0156] Preferably, X8, X9 and X 10 is O, S, or SO2. Particularly preferred are X8, X9, and X 10 is O. Particularly preferred are X8, X9 and X 10 is S. Particularly preferred are X8, X9 and X 10 is SO2.

[0157] Preferably, p and q are each independently 1, 3, 3, 4, 5 or 6, particularly preferably 1 or 2, and very particularly preferably 2.

[0158] Preferably, r and u are each independently 0, 1, 2 or 3, particularly preferably 0, 1 or 2, very particularly preferably 0.

[0159] When o is 0, -R2- is a bond.

[0160] According to the present invention, suitable examples of -R2- are -(CH2)-, -(CH2)2-, -(CH2)3-, -(CH2)4-, -(CH2)5-, -(CH2)6-, -(CH2)7-, -(CH2)8-, -(CH2)9-, -(CH2) 10 -, -(CH2) 11 -, -(CH2) 12 -, -(CH2) 13 -, -(CH2) 14 -, -(CH2) 15 -, -(CH2) 16 -, -(CH2) 17 -, -(CH2) 18 -, -(CH2) 19 -, -(CH2) 20 -, -(CHCH3)-, -(CHCH3)2-, -(CHCH3)3-, -(CHCH3)4-, -(CHCH3)5-, -(CHCH3)6-, -(CHCH3)7-, -(CHCH3)8-, -(CHCH3)9-, -(CHCH3) 10 -, -(CHCH3) 11 -, -(CHCH3) 12 -, -(CHCH3) 13 -, -(CHCH3) 14 -, -(CHCH3) 15 -, -(CHCH3) 16 -, -(CHCH3) 17 -, -(CHCH3) 18 -, -(CHCH3) 19 -, -(CHCH3) 20-、-(C(CH3)2)-、-(C(CH3)2)2-、-(C(CH3)2)3-、-(C(CH3)2)4-、-(C(CH3)2)5-、-(C(CH3)2)6-、-(C(CH3)2)7-、-(C(CH3)2)8-、-(C(CH3)2)9-、-(C(CH3)2) 10 -、-(C(CH3)2) 11 -、-(C(CH3)2) 12 -、-(C(CH3)2) 13 -、-(C(CH3)2) 14 -、-(C(CH3)2) 15 -、-(C(CH3)2) 16 -、-(C(CH3)2) 17 -、-(C(CH3)2) 18 -、-(C(CH3)2) 19 -、-(C(CH3)2) 20 -、-(CHC2H5)-、-(CHC2H5)2-、-(CHC2H5)3-、-(CHC2H5)4-、-(CHC2H5)5-、-(CHC2H5)6-、-(CHC2H5)7-、-(CHC2H5)8-、-(CHC2H5)9-、-(CHC2H5) 10 -、-(CHC2H5) 11 -、-(CHC2H5) 12 -、-(CHC2H5) 13 -、-(CHC2H5) 14 -、-(CHC2H5) 15 -、-(CHC2H5) 16 -、-(CHC2H5) 17 -、-(CHC2H5) 18 -、-(CHC2H5) 19 -、-(CHC2H5) 20 -、-(CH2)-(CHCH3)-(CH2)-、-(CH2)-(CHCH3)-(CH2)2-、-(CH2)-(CHCH3)-(CH2)3-、-(CH2)-(CHCH3)-(CH2) 11 -、-(CH2)2-(CHCH3)-(CH2)-、-(CH2)3-(CHCH3)-(CH2)-、-(CH2) 11-(CHCH3)-(CH2)-、-(CH2)2-O-(CH2)2-、-(CH2)3-O-(CH2)3-、-(CH2)2-O -(CH2)2-O-(CH2)2-、-(CH2)3-O-(CH2)3-O-(CH2)3-、-(CH2)2-O-(CH2)2 -O-(CH2)6-、-(CH2)6-O-(CH2)2-O-(CH2)2-、-(CH2)2-O-(CH2)2-O-(CH2 )8-、-(CH2)8-O-(CH2)2-O-(CH2)2-、-(CH2)2-S-(CH2)2-、-(CH2)3-S-(C H2)3-、-(CH2)2-S-(CH2)2-S-(CH2)2-、-(CH2)3-S-(CH2)3-S-(CH2)3-、- (CH2)2-S-(CH2)2-S-(CH2)6-、-(CH2)6-S-(CH2)2-S-(CH2)2-、-(CH2)2- S-(CH2)2-S-(CH2)8-、-(CH2)8-S-(CH2)2-S-(CH2)2-、-(CH2)2-SO2-(CH2)2-、-(CH2)3-SO2-(CH2)3-、-(CH2)2-SO2-(CH2)2-SO2-(CH2)2-、-(CH2) 3-SO2-(CH2)3-SO2-(CH2)3-、-(CH2)2-SO2-(CH2)2-SO2-(CH2)6-、-(CH2)6-SO2-(CH2)2-SO2-(CH2)2-、-(CH2)2-SO2-(CH2)2-SO2-(CH2)8-、-(CH2)8-SO2-(CH2)2-SO2-(CH2)2-、-(CH2)-S-(CH2)2-O-(CH2)-、-(CH2)-SO2-(CH2)2-O-(CH2)-、-(CH2)-SO2-(CH2)2-S-(CH2)-、-(CH2)-O-(CH2)2-S -(CH2)2-O-(CH2)-、-(CH2)-S-(CH2)2-O-(CH2)2-S-(CH2)-、-(CH2)-SO2-(CH2)2-SO2-(CH2)-、-(CH2)-S-(CH2)2-S-(CH2)2-S-(CH2)-、-(CH2)-SO2-(CH2)2-SO2-(CH2)2-SO2-(CH2)-、-(CH2)-O-(CH2)2-SO2-(CH2)2-O-(CH2)-、-(CH2)2-(NCH3)-(CH2)2-、-(CH2)3-(NCH3)-(CH2)3-、-(CH2)2-(NCH3)-(CH2)2-(NCH3)-(CH2)2-, -(CH2)3-(NCH3)-(CH2)3-(NCH3)-(CH2)3-, -(CH2)2-(NCH3)-(CH2)2-(NCH3)-(CH2)6-, -(CH2)6-(NCH3)-(CH2)2-(NCH3)-(CH2)2-, -(CH2)2-(NCH3)-(CH2)2-(NCH3)-(CH2)8- and -(CH2)8-(NCH3)-(CH2)2-(NCH3)-(CH2)2-; -(CF2)-(CH2)-, -(CH2)-(CF2)-, -(CH2)-(CF2)-(CH2)-, -(CH2)-(CF2)-(CH2)2-, -(CH2)-(CF2)-(CH2)3-, -(CH2)-(CF2)-(CH2)4-, -(CH2) -(CF2)-(CH2)5-, -(CH2)-(CF2)-(CH2)6-, -(CH2)-(CF2)-(CH2)7-, -(CH2)-(CF2)-(CH2)8-, -(CH2)-(CF2)-(CH2)9-, -(CH2)-(CF2)-(CH2) 10 -, -(CH2)2-(CF2)-(CH2)-, -(CH2)3-(CF2)-(CH2)-, -(CH2)4-(CF2)-(CH2)-, -(CH2)5-(CF2)-(CH2)-, -( CH2)6-(CF2)-(CH2)-, -(CH2)7-(CF2)-(CH2)-, -(CH2)8-(CF2)-(CH2)-, -(CH2)9-(CF2)-(CH2)-, -(CH2) 10-(CF2)-(CH2)-、-(CH2)2-(CF2)-(CH2)2-、-(CH2)3-(CF2)-(CH2)3-、-(CH2)4-(CF2)-(CH2)4-、-(CH2)5-(CF2)-(CH2)5-、-(CH2)2-(CF2)-(CH2)-、-(CH2)2-(CF2)-(CH2)3-、-(CH2)2-(CF2)-(CH2)4-、-(CH2)2-(CF2)-(CH2)5-、-(CH2)2-(CF2)-(CH2)6-、-(CH2)2-(CF2)-(CH2)7-、-(CH2)2-(CF2)-(CH2)8-、-(CH2)2-(CF2)-(CH2)9-、-(CH2)3-(CF2)-(CH2)-、-(CH2)3-(CF2)-(CH2)2-、-(CH2)3-(CF2)-(CH2)4-、-(CH2)3-(CF2)-(CH2)5-、-(CH2)3-(CF2)-(CH2)6-、-(CH2)3-(CF2)-(CH2)7-、-(CH2)3-(CF2)-(CH2)8-、-(CH2)4-(CF2)-(CH2)-、-(CH2)4-(CF2)-(CH2)2-、-(CH2)4-(CF2)-(CH2)3-、-(CH2)4-(CF2)-(CH2)5-、-(CH2)4-(CF2)-(CH2)6-、-(CH2)4-(CF2)-(CH2)7-、-(CH2)5-(CF2)-(CH2)-、-(CH2)5-(CF2)-(CH2)2-、-(CH2)5-(CF2)-(CH2)3-、-(CH2)5-(CF2)-(CH2)4-、-(CH2)5-(CF2)-(CH2)6-、-(CH2)6-(CF2)-(CH2)-、-(CH2)6-(CF2)-(CH2)2-、-(CH2)6-(CF2)-(CH2)3-、-(CH2)6-(CF2)-(CH2)4-、-(CH2)6-(CF2)-(CH2)5-、 -(CFH)-(CH2)-、-(CH2)-(CFH)-、-(CH2)-(CFH)-(CH2)-、-(CH2)-(CFH)-(CH2)2-、-(CH2)-(CFH)-(CH2)3-、-(CH2)-(CFH)-(CH2)4-、-(CH2)-(CFH)-(CH2)5-、-(CH2)-(CFH)-(CH2)6-、-(CH2)-(CFH)-(CH2)7-、-(CH2)-(CFH)-(CH2)8-、-(CH2)-(CFH)-(CH2)9-、-(CH2)-(CFH)-(CH2) 10 -、-(CH2)2-(CFH)-(CH2)-、-(CH2)3-(CFH)-(CH2)-、-(CH2)4-(CFH)-(CH2)-、-(CH2)5-(CFH)-(CH2)-、-(CH2)6-(CFH)-(CH2)-、-(CH2)7-(CFH)-(CH2)-、-(CH2)8-(CFH)-(CH2)-、-(CH2)9-(CFH)-(CH2)-、-(CH2) 10-(CFH)-(CH2)-、-(CH2)2-(CFH)-(CH2)2-、-(CH2)3-(CFH)-(CH2)3-、-(CH2)4-(CFH)-(CH2)4-、-(CH2)5-(CFH)-(CH2)5-、-(CH2)2-(CFH)-(CH2)-、-(CH2)2-(CFH)-(CH2)3-、-(CH2)2-(CFH)-(CH2)4-、-(CH2)2-(CFH)-(CH2)5-、-(CH2)2-(CFH)-(CH2)6-、-(CH2)2-(CFH)-(CH2)7-、-(CH2)2-(CFH)-(CH2)8-、-(CH2)2-(CFH)-(CH2)9-、-(CH2)3-(CFH)-(CH2)-、-(CH2)3-(CFH)-(CH2)2-、-(CH2)3-(CFH)-(CH2)4-、-(CH2)3-(CFH)-(CH2)5-、-(CH2)3-(CFH)-(CH2)6-、-(CH2)3-(CFH)-(CH2)7-、-(CH2)3-(CFH)-(CH2)8-、-(CH2)4-(CFH)-(CH2)-、-(CH2)4-(CFH)-(CH2)2-、-(CH2)4-(CFH)-(CH2)3-、-(CH2)4-(CFH)-(CH2)5-、-(CH2)4-(CFH)-(CH2)6-、-(CH2)4-(CFH)-(CH2)7-、-(CH2)5-(CFH)-(CH2)-、-(CH2)5-(CFH)-(CH2)2-、-(CH2)5-(CFH)-(CH2)3-、-(CH2)5-(CFH)-(CH2)4-、-(CH2)5-(CFH)-(CH2)6-、-(CH2)6-(CFH)-(CH2)-、-(CH2)6-(CFH)-(CH2)2-、-(CH2)6-(CFH)-(CH2)3-、-(CH2)6-(CFH)-(CH2)4-、-(CH2)6-(CFH)-(CH2)5-、 -(CF2)2-(CH2)-、-(CH2)-(CF2)2-、-(CH2)-(CF2)2-(CH2)-、-(CH2)-(CF2)2-(CH2)2-、-(CH2)-(CF2)2-(CH2)3-、-(CH2)-(CF2)2-(CH2)4-、-(CH2)-(CF2)2-(CH2)5-、-(CH2)-(CF2)2-(CH2)6-、-(CH2)-(CF2)2-(CH2)7-、-(CH2)-(CF2)2-(CH2)8-、-(CH2)-(CF2)2-(CH2)9-、-(CH2)2-(CF2)2-(CH2)-、-(CH2)3-(CF2)2-(CH2)-、-(CH2)4-(CF2)2-(CH2)-、-(CH2)5-(CF2)2-(CH2)-、-(CH2)6-(CF2)2-(CH2)-、-(CH2)7-(CF2)2-(CH2)-、-(CH2)8-(CF2)2-(CH2)-、-(CH2)9-(CF2)2-(CH2)-、-(CH2)2-(CF2)2-(CH2)2-、-(CH2)3-(CF2)2-(CH2)3-、-(CH2)4-(CF2)2-(CH2)4-、-(CH2)5-(CF2)2-(CH2)5-、-(CH2)2-(CF2)2-(CH2)-、-(CH2)2-(CF2)2-(CH2)3-、-(CH2)2-(CF2)2-(CH2)4-、-(CH2)2-(CF2)2-(CH2)5-、-(CH2)2-(CF2)2-(CH2)6-、-(CH2)2-(CF2)2-(CH2)7-、-(CH2)2-(CF2)2-(CH2)8-、-(CH2)3-(CF2)2-(CH2)-、-(CH2)3-(CF2)2-(CH2)2-、-(CH2)3-(CF2)2-(CH2)4-、-(CH2)3-(CF2)2-(CH2)5-、-(CH2)3-(CF2)2-(CH2)6-、-(CH2)3-(CF2)2-(CH2)7-、-(CH2)4-(CF2)2-(CH2)-、-(CH2)4-(CF2)2-(CH2)2-、-(CH2)4-(CF2)2-(CH2)3-、-(CH2)4-(CF2)2-(CH2)5-、-(CH2)4-(CF2)2-(CH2)6-、-(CH2)5-(CF2)2-(CH2)-、-(CH2)5-(CF2)2-(CH2)2-、-(CH2)5-(CF2)2-(CH2)3-、-(CH2)5-(CF2)2-(CH2)4-、-(CH2)6-(CF2)2-(CH2)-、-(CH2)6-(CF2)2-(CH2)2-、-(CH2)6-(CF2)2-(CH2)3-、-(CH2)6-(CF2)2-(CH2)4-、 -(CFH)2-(CH2)-、-(CH2)-(CFH)2-、-(CH2)-(CFH)2-(CH2)-、-(CH2)-(CFH)2-(CH2)2-、-(CH2)-(CFH)2-(CH2)3-、-(CH2)-(CFH)2-(CH2)4-、-(CH2)-(CFH)2-(CH2)5-、-(CH2)-(CFH)2-(CH2)6-、-(CH2)-(CFH)2-(CH2)7-、-(CH2)-(CFH)2-(CH2)8-、-(CH2)-(CFH)2-(CH2)9-、-(CH2)2-(CFH)2-(CH2)-、-(CH2)3-(CFH)2-(CH2)-、-(CH2)4-(CFH)2-(CH2)-、-(CH2)5-(CFH)2-(CH2)-、-(CH2)6-(CFH)2-(CH2)-、-(CH2)7-(CFH)2-(CH2)-、-(CH2)8-(CFH)2-(CH2)-、-(CH2)9-(CFH)2-(CH2)-、-(CH2)2-(CFH)2-(CH2)2-、-(CH2)3-(CFH)2-(CH2)3-、-(CH2)4-(CFH)2-(CH2)4-、-(CH2)5-(CFH)2-(CH2)5-、-(CH2)2-(CFH)2-(CH2)-、-(CH2)2-(CFH)2-(CH2)3-、-(CH2)2-(CFH)2-(CH2)4-、-(CH2)2-(CFH)2-(CH2)5-、-(CH2)2-(CFH)2-(CH2)6-、-(CH2)2-(CFH)2-(CH2)7-、-(CH2)2-(CFH)2-(CH2)8-、-(CH2)3-(CFH)2-(CH2)-、-(CH2)3-(CFH)2-(CH2)2-、-(CH2)3-(CFH)2-(CH2)4-、-(CH2)3-(CFH)2-(CH2)5-、-(CH2)3-(CFH)2-(CH2)6-、-(CH2)3-(CFH)2-(CH2)7-、-(CH2)4-(CFH)2-(CH2)-、-(CH2)4-(CFH)2-(CH2)2-、-(CH2)4-(CFH)2-(CH2)3-、-(CH2)4-(CFH)2-(CH2)5-、-(CH2)4-(CFH)2-(CH2)6-、-(CH2)5-(CFH)2-(CH2)-、-(CH2)5-(CFH)2-(CH2)2-、-(CH2)5-(CFH)2-(CH2)3-、-(CH2)5-(CFH)2-(CH2)4-、-(CH2)6-(CFH)2-(CH2)-、-(CH2)6-(CFH)2-(CH2)2-、-(CH2)6-(CFH)2-(CH2)3-、-(CH2)6-(CFH)2-(CH2)4-、 -(CF2)3-(CH2)-、-(CH2)-(CF2)3-、-(CH2)-(CF2)3-(CH2)-、-(CH2)-(CF2)3-(CH2)2-、-(CH2)-(CF2)3-(CH2)3-、-(CH2)-(CF2)3-(CH2)4-、-(CH2)-(CF2)3-(CH2)5-、-(CH2)-(CF2)3-(CH2)6-、-(CH2)-(CF2)3-(CH2)7-、-(CH2)-(CF2)3-(CH2)8-、-(CH2)2-(CF2)3-(CH2)-、-(CH2)3-(CF2)3-(CH2)-、-(CH2)4-(CF2)3-(CH2)-、-(CH2)5-(CF2)3-(CH2)-、-(CH2)6-(CF2)3-(CH2)-、-(CH2)7-(CF2)3-(CH2)-、-(CH2)8-(CF2)3-(CH2)-、-(CH2)2-(CF2)3-(CH2)2-、-(CH2)3-(CF2)3-(CH2)3-、-(CH2)4-(CF2)3-(CH2)4-、-(CH2)2-(CF2)3-(CH2)-、-(CH2)2-(CF2)3-(CH2)3-、-(CH2)2-(CF2)3-(CH2)4-、-(CH2)2-(CF2)3-(CH2)5-、-(CH2)2-(CF2)3-(CH2)6-、-(CH2)2-(CF2)3-(CH2)7-、-(CH2)3-(CF2)3-(CH2)-、-(CH2)3-(CF2)3-(CH2)2-、-(CH2)3-(CF2)3-(CH2)4-、-(CH2)3-(CF2)3-(CH2)5-、-(CH2)3-(CF2)3-(CH2)6-、-(CH2)4-(CF2)3-(CH2)-、-(CH2)4-(CF2)3-(CH2)2-、-(CH2)4-(CF2)3-(CH2)3-、-(CH2)4-(CF2)3-(CH2)5-、-(CH2)5-(CF2)3-(CH2)-、-(CH2)5-(CF2)3-(CH2)2-、-(CH2)5-(CF2)3-(CH2)3-、-(CH2)5-(CF2)3-(CH2)4-、(CH2)6-(CF2)3-(CH2)-、-(CH2)6-(CF2)3-(CH2)2-、-(CH2)6-(CF2)3-(CH2)3-、 -(CF2)4-(CH2)-、-(CH2)-(CF2)4-、-(CH2)-(CF2)4-(CH2)-、-(CH2)-(CF2)4-(CH2)2-、-(CH2)-(CF2)4-(CH2)3-、-(CH2)-(CF2)4-(CH2)4-、-(CH2)-(CF2)4-(CH2)5-、-(CH2)-(CF2)4-(CH2)6-、-(CH2)-(CF2)4-(CH2)7-、-(CH2)-(CF2)4-(CH2)8-、-(CH2)-(CF2)4-(CH2)9-、-(CH2)-(CF2)4-(CH2) 10 -、-(CH2)2-(CF2)4-(CH2)-、-(CH2)3-(CF2)4-(CH2)-、-(CH2)4-(CF2)4-(CH2)-、-(CH2)5-(CF2)4-(CH2)-、-(CH2)6-(CF2)4-(CH2)-、-(CH2)7-(CF2)4-(CH2)-、-(CH2)2-(CF2)4-(CH2)2-、-(CH2)3-(CF2)4-(CH2)3-、-(CH2)4-(CF2)4-(CH2)4-、-(CH2)5-(CF2)4-(CH2)5-、-(CH2)2-(CF2)4-(CH2)3-、-(CH2)2-(CF2)4-(CH2)4-、-(CH2)2-(CF2)4-(CH2)5-、-(CH2)2-(CF2)4-(CH2)6-、-(CH2)3-(CF2)4-(CH2)2-、-(CH2)3-(CF2)4-(CH2)4-、-(CH2)4-(CF2)4-(CH2)2-、-(CH2)4-(CF2)4-(CH2)3-、-(CH2)5-(CF2)4-(CH2)2-、-(CH2)5-(CF2)4-(CH2)3-、-(CH2)6-(CF2)4-(CH2)2-、 -(CF2)5-(CH2)-、-(CH2)-(CF2)5-、-(CH2)-(CF2)5-(CH2)-、-(CH2)-(CF2)5-(CH2)2-、-(CH2)-(CF2)5-(CH2)3-、-(CH2)-(CF2)5-(CH2)4-、-(CH2)-(CF2)5-(CH2)5-、-(CH2)-(CF2)5-(CH2)6-、-(CH2)2-(CF2)5-(CH2)-、-(CH2)3-(CF2)5-(CH2)-、-(CH2)4-(CF2)5-(CH2)-、-(CH2)5-(CF2)5-(CH2)-、-(CH2)6-(CF2)5-(CH2)-、-(CH2)2-(CF2)5-(CH2)2-、-(CH2)3-(CF2)5-(CH2)3-、-(CH2)4-(CF2)5-(CH2)4-、-(CH2)2-(CF2)5-(CH2)3-、-(CH2)2-(CF2)5-(CH2)4-、-(CH2)2-(CF2)5-(CH2)5-、-(CH2)2-(CF2)5-(CH2)6-、-(CH2)3-(CF2)5-(CH2)2-、-(CH2)3-(CF2)5-(CH2)4-、-(CH2)4-(CF2)5-(CH2)2-、-(CH2)4-(CF2)5-(CH2)3-、-(CH2)5-(CF2)5-(CH2)2-、 -(CHCF3)-(CH2)-、-(CH2)-(CHCF3)-、-(CH2)-(CHCF3)-(CH2)-、-(CH2)-(CHCF3)-(CH2)2-、-(CH2)-(CHCF3)-(CH2)3-、-(CH2)-(CHCF3)-(CH2)4-、-(CH2)-(CHCF3)-(CH2)5-、-(CH2)-(CHCF3)-(CH2)6-、-(CH2)-(CHCF3)-(CH2)7-、-(CH2)-(CHCF3)-(CH2)8-、-(CH2)-(CHCF3)-(CH2)9-、-(CH2)-(CHCF3)-(CH2) 10-、-(CH2)2-(CHCF3)-(CH2)-、-(CH2)3-(CHCF3)-(CH2)-、-(CH2)4-(CHCF3)-(CH2)-、-(CH2)5-(CHCF3)-(CH2)-、-(CH2)6-(CHCF3)-(CH2)-、-(CH2)7-(CHCF3)-(CH2)-、-(CH2)8-(CHCF3)-(CH2)-、-(CH2)9-(CHCF3)-(CH2)-、-(CH2) 10 -(CHCF3)-(CH2)-、-(CH2)2-(CHCF3)-(CH2)2-、-(CH2)3-(CHCF3)-(CH2)3-、-(CH2)4-(CHCF3)-(CH2)4-、-(CH2)5-(CHCF3)-(CH2)5-、-(CH2)2-(CHCF3)-(CH2)3-、-(CH2)2-(CHCF3)-(CH2)4-、-(CH2)2-(CHCF3)-(CH2)5-、 -(CH2)2-(CHCF3)-(CH2)6-、-(CH2)2-(CHCF3)-(CH2)7-、-(CH2)2-(CHCF3)-(CH2)8-、-(CH2)2-(CHCF3)-(CH2)9-、-(CH2)3-(CHCF3)-(CH2)2-、-(CH2)3-(CHCF3)-(CH2)4-、-(CH2)3-(CHCF3)-(CH2)5-、-(CH2)3-(CHCF3)- (CH2)6-、-(CH2)3-(CHCF3)-(CH2)7-、-(CH2)3-(CHCF3)-(CH2)8-、-(CH2)4-(CHCF3)-(CH2)2-、-(CH2)4-(CHC) F3)-(CH2)3-、-(CH2)4-(CHCF3)-(CH2)5-、-(CH2)4-(CHCF3)-(CH2)6-、-(CH2)4-(CHCF3)-(CH2)7-、-(CH2)5- (CHCF3)-(CH2)2-、-(CH2)5-(CHCF3)-(CH2)3-、-(CH2)5-(CHCF3)-(CH2)4-、-(CH2)5-(CHCF3)-(CH2)6-、-(CH2)6-(CHCF3)-(CH2)2-、-(CH2)6-(CHCF3)-(CH2)3-、-(CH2)6-(CHCF3)-(CH2)4-、-(CH2)6-(CHCF3)-(CH2)5-、 -(CHCF3)2-(CH2)-、-(CH2)-(CHCF3)2-、-(CH2)-(CHCF3)2-(CH2)-、-(CH2)-(CHCF3)2-(CH2)2-、-(CH2)-(CHCF3)2-(CH2)3-、-(CH2)-(CHCF3)2-(CH2)4-、-(CH2)-(CHCF3)2-(CH2)5-、-(CH2)-(CHCF3)2-(CH2)6-、-(CH2)-(CHCF3)2-(CH2)7-、-(CH2)-(CHCF3)2-(CH2)8-、-(CH2)-(CHCF3)2-(CH2)9 (CH2)2-(CHCF3)2-(CH2)-、-(CH2)3-(CHCF3)2-(CH2)-、-(CH2)4-(CHCF3)2-(CH2)- CH2)7-(CHCF3)2-(CH2)-、-(CH2)8-(CHCF3)2-(CH2)-、-(CH2)9-(CHCF3)2-(CH2)-、-(CH2)2-(CHCF3)2-(CH2)2-、-(CH2)3-(CHCF3)2-(CH2)3-、-(CH 2)4-(CHCF3)2-(CH2)4-、-(CH2)5-(CHCF3)2-(CH2)5-、-(CH2)2-(CHCF3)2-(CH2)3-、-(CH2)2-(CHCF3)2-(CH2)4-、-(CH2)2-(CHCF3)2-(CH2)5-、-(CH2)2-(CHCF3)2-(CH2)6-、-(CH2)2-(CHCF3)2-(CH2)7-、-(CH2)2-(CHCF3)2-(CH2)8-、-(CH2)3-(CHCF3)2-(CH2)2-、-(CH2)3-(CHCF3)2-(CH2)4-、-( CH2)3-(CHCF3)2-(CH2)5-、-(CH2)3-(CHCF3)2-(CH2)6-、-(CH2)3-(CHCF3)2-(CH2)7-、-(CH2)4-(CHCF3)2-(CH2)2-、-(CH2)4-(CHCF3)2-(CH2)3-、-(CH2)4-(CHCF3)2-(CH2)5-、-(CH2)4-(CHCF3)2-(CH2)6-、-(CH2)5-(CHCF3)2-(CH2)2-、-(CH2)5-(CHCF3)2-(CH2)3-、-(CH2)5-(CHCF3)2-(CH2)4-、-(CH2)6-(CHCF3)2-(CH2)2-、-(CH2)6-(CHCF3)2-(CH2)3-、-(CH2)6-(CHCF3)2-(CH2)4-、 -(CHCF3)3-(CH2)-、-(CH2)-(CHCF3)3-、-(CH2)-(CHCF3)3-(CH2)-、-(CH2)-(CHCF3)3-(CH2)2-、-(CH2)-(CHCF3)3-(CH2)3-、-(CH2)-(CHCF3)3-(CH2)4-、-(CH2)-(CHCF3)3-(CH2)5-、-(CH2)-(CHCF3)3-(CH2)6-、-(CH2)-(CHCF3)3-(CH2)7-、-(CH2)-(CHCF3)3-(CH2)8 -、-(CH2)2-(CHCF3)3-(CH2)-、-(CH2)3-(CHCF3)3-(CH2)-、-(CH2)4-(CHCF3)3-(CH2)-、-(CH2)5-(CHCF3)3-(CH2)-、-(CH2)6-(CHCF3)3-(CH2)-、-(CH2)7-(CHCF3)3-(CH2)-、-(CH2)8-(CHCF3)3-(CH2)-、-(CH2)2-(CHCF3)3-(CH2)2-、-(CH2)3-(CHCF3)3-(CH2)3-、-(C H2)4-(CHCF3)3-(CH2)4-、-(CH2)2-(CHCF3)3-(CH2)3-、-(CH2)2-(CHCF3)3-(CH2)4-、-(CH2)2-(CHCF3)3-(CH2)5-、-(CH2)2-(CHCF3)3-(CH2)6-、-(CH2)2-(CHCF3)3-(CH2)7-、-(CH2)3-(CHCF3)3-(CH2)2-、-(CH2)3-(CHCF3)3-(CH2)4-、-(CH2)3-(CHCF3)3-(CH2)5-、- (CH2)3-(CHCF3)3-(CH2)6-、-(CH2)4-(CHCF3)3-(CH2)2-、-(CH2)4-(CHCF3)3-(CH2)3-、-(CH2)4-(CHCF3)3-(CH2)5-、-(CH2)5-(CHCF3)3-(CH2)2-、-(CH2)5-(CHCF3)3-(CH2)3-、-(CH2)5-(CHCF3)3-(CH2)4-、-(CH2)6-(CHCF3)3-(CH2)2-、-(CH2)6-(CHCF3)3-(CH2)3-、 -(CHCF3)4-(CH2)-、-(CH2)-(CHCF3)4-、-(CH2)-(CHCF3)4-(CH2)-、-(CH2)-(CHCF3)4-(CH2)2-、-(CH2)-(CHCF3)4-(CH2)3-、-(CH2)-(CHCF3)4-(CH2)4-、-(CH2)-(CHCF3)4-(CH2)5-、-(CH2)-(CHCF3)4-(CH2)6-、-(CH2)-(CHCF3)4-(CH2)7-、-(CH2)-(CHCF3)4-(CH2)8-、-(CH2)-(CHCF3)4-(CH2)9-、-(CH2)-(CHCF3)4-(CH2) 10 -、-(CH2)2-(CHCF3)4-(CH2)-、-(CH2)3-(CHCF3)4-(CH2)-、-(CH2)4-(CHCF3)4-(CH2)-、-(CH2)5-(CHCF3)4-(CH2)-、-(CH2)6-(CHCF3)4-(CH2)-、-(CH2)7-(CHCF3)4-(CH2)-、-(CH2)2-(CHCF3)4-(CH2)2-、-(CH2)3-(CHCF3)4-(CH2)3-、-(CH2)4-(CHCF3)4-(CH2)4-、-(CH2)5-(CHCF3)4-(CH2)5-、-(CH2)2-(CHCF3 )4-(CH2)3-、-(CH2)2-(CHCF3)4-(CH2)4-、-(CH2)2-(CHCF3)4-(CH2)5-、-(CH2)2-(CHCF3)4-(CH2)6-、-(CH2)3-(CHCF3)4-(CH2)2-、-(CH2)3-(CHCF3)4-(CH2)4-、-(CH2)4-(CHCF3)4-(CH2)2-、-(CH2)4-(CHCF3)4-(CH2)3-、-(CH2)5-(CHCF3)4-(CH2)2-、-(CH2)5-(CHCF3)4-(CH2)3-、-(CH2)6-(CHCF3)4-(CH2)2-、 -(CHCF3)5-(CH2)-、-(CH2)-(CHCF3)5-、-(CH2)-(CHCF3)5-(CH2)-、-(CH2)-(CHCF3)5-(CH2)2-、-(CH2)-(CHCF3)5-(CH2)3-、-(CH2)-(CHCF3)5-(CH2)4-、-(CH2)-(CHCF3)5-(CH2 )5-、-(CH2)-(CHCF3)5-(CH2)6-、-(CH2)2-(CHCF3)5-(CH2)-、-(CH2)3-(CHCF3)5-(CH2)-、-(CH2)4-(CHCF3)5-(CH2)-、-(CH2)5-(CHCF3)5-(CH2)-、-(CH2)6-(CHCF3)5-(CH2)-、- (CH2)2-(CHCF3)5-(CH2)2-、-(CH2)3-(CHCF3)5-(CH2)3-、-(CH2)4-(CHCF3)5-(CH2)4-、-(CH2)2-(CHCF3)5-(CH2)3-、-(CH2)2-(CHCF3)5-(CH2)4-、-(CH2)2-(CHCF3)5-(CH2)5-、 -(CH2)2-(CHCF3)5-(CH2)6-、-(CH2)3-(CHCF3)5-(CH2)2-、-(CH2)3-(CHCF3)5-(CH2)4-、-(CH2)4-(CHCF3)5-(CH2)2-、-(CH2)4-(CHCF3)5-(CH2)3-、-(CH2)5-(CHCF3)5-(CH2)2-、 -[C(CH3)CF3]-(CH2)-、-(CH2)-[C(CH3)CF3]-、-(CH2)-[C(CH3)CF3]-(CH2)-、-(CH2)-[C( CH3)CF3]-(CH2)2-、-(CH2)-[C(CH3)CF3]-(CH2)3-、-(CH2)-[C(CH3)CF3]-(CH2)4-、-(CH2) -[C(CH3)CF3]-(CH2)5-、-(CH2)-[C(CH3)CF3]-(CH2)6-、-(CH2)-[C(CH3)CF3]-(CH2)7-、- (CH2)-[C(CH3)CF3]-(CH2)8-、-(CH2)-[C(CH3)CF3]-(CH2)9-、-(CH2)-[C(CH3)CF3]-(CH2) 10-、-(CH2)2-[C(CH3)CF3]-(CH2)-、-(CH2)3-[C(CH3)CF3]-(CH2)-、-(CH2)4-[C(CH3)CF3]-(CH2)-、-(CH2)5-[C(CH3)CF3]-(CH2)-、-(CH2)6-[C(CH3)CF3]-(CH2)-、-(CH2)7-[C(CH3)CF3]-(CH2)-、-(CH2)8-[C(CH3)CF3]-(CH2)-、-(CH2)9-[C(CH3)CF3]-(CH2)-、-(CH2) 10-[C(CH3)CF3]-(CH2)-、-(CH2)2-[C(CH3)CF3]-(CH2)2-、-(CH2)3-[C(CH3)CF3]-(CH2)3-、-(CH2)4-[C(CH3)CF3]-(CH2)4-、-(CH2)5-[C(CH3)CF3]-(CH2)5-、-(CH2)2-[C(CH3)CF3]-(CH2)3-、-(CH2)2-[C(CH3)CF3]-(CH2)4-、-(CH2)2-[C(CH3)CF3]-(CH2)5-、-(CH2)2-[C(CH3)CF3]-(CH2)6-、-(CH2)2-[C(CH3)CF3]-(CH2)7-、-(CH2)2-[C(CH3)CF3]-(CH2)8-、-(CH2)2-[C(CH3)CF3]-(CH2)9-、-(CH2)3-[C(CH3)CF3]-(CH2)2-、-(CH2)3-[C(CH3)CF3]-(CH2)4-、-(CH2)3-[C(CH3)CF3]-(CH2)5-、-(CH2)3-[C(CH3)CF3]-(CH2)6-、-(CH2)3-[C(CH3)CF3]-(CH2)7-、-(CH2)3-[C(CH3)CF3]-(CH2)8-、-(CH2)4-[C(CH3)CF3]-(CH2)2-、-(CH2)4-[C(CH3)CF3]-(CH2)3-、-(CH2)4-[C(CH3)CF3]-(CH2)5-、-(CH2)4-[C(CH3)CF3]-(CH2)6-、-(CH2)4-[C(CH3)CF3]-(CH2)7-、-(CH2)5-[C(CH3)CF3]-(CH2)2-、-(CH2)5-[C(CH3)CF3]-(CH2)3-、-(CH2)5-[C(CH3)CF3]-(CH2)4-、-(CH2)5-[C(CH3)CF3]-(CH2)6-、-(CH2)6-[C(CH3)CF3]-(CH2)2-、-(CH2)6-[C(CH3)CF3]-(CH2)3-、-(CH2)6-[C(CH3)CF3]-(CH2)4-、-(CH2)6-[C(CH3)CF3]-(CH2)5-、 -[C(CH3)CF3]2-(CH2)-、-(CH2)-[C(CH3)CF3]2-、-(CH2)-[C(CH3)CF3]2-(CH2)-、-(CH2)-[C(CH3)CF3]2-(CH2)2-、-(CH2)-[C(CH3)CF3]2-(CH2)3-、-(CH2)-[C(CH3)CF3]2-(CH2)4-、-(CH2)-[C(CH3)CF3]2-(CH2)5-、-(CH2)-[C(CH3)CF3]2-(CH2)6-、-(CH2)-[C(CH3)CF3]2-(CH2)7-、-(CH2)-[C(CH3)CF3]2-(CH2)8-、-(CH2)-[C(CH3)CF3]2-(CH2)9-、-(CH2)2-[C(CH3)CF3]2-(CH2)-、-(CH2)3-[C(CH3)CF3]2-(CH2)-、-(CH2)4-[C(CH3)CF3]2-(CH2)-、-(CH2)5-[C(CH3)CF3]2-(CH2)-、-(CH2)6-[C(CH3)CF3]2-(CH2)-、-(CH2)7-[C(CH3)CF3]2-(CH2)-、-(CH2)8-[C(CH3)CF3]2-(CH2)-、-(CH2)9-[C(CH3)CF3]2-(CH2)-、-(CH2)2-[C(CH3)CF3]2-(CH2)2-、-(CH2)3-[C(CH3)CF3]2-(CH2)3-、-(CH2)4-[C(CH3)CF3]2-(CH2)4-、-(CH2)5-[C(CH3)CF3]2-(CH2)5-、-(CH2)2-[C(CH3)CF3]2-(CH2)3-、-(CH2)2-[C(CH3)CF3]2-(CH2)4-、-(CH2)2-[C(CH3)CF3]2-(CH2)5-、-(CH2)2-[C(CH3)CF3]2-(CH2)6-、-(CH2)2-[C(CH3)CF3]2-(CH2)7-、-(CH2)2-[C(CH3)CF3]2-(CH2)8-、-(CH2)3-[C(CH3)CF3]2-(CH2)2-、-(CH2)3-[C(CH3)CF3]2-(CH2)4-、-(CH2)3-[C(CH3)CF3]2-(CH2)5-、-(CH2)3-[C(CH3)CF3]2-(CH2)6-、-(CH2)3-[C(CH3)CF3]2-(CH2)7-、-(CH2)4-[C(CH3)CF3]2-(CH2)2-、-(CH2)4-[C(CH3)CF3]2-(CH2)3-、-(CH2)4-[C(CH3)CF3]2-(CH2)5-、-(CH2)4-[C(CH3)CF3]2-(CH2)6-、-(CH2)5-[C(CH3)CF3]2-(CH2)2-、-(CH2)5-[C(CH3)CF3]2-(CH2)3-、-(CH2)5-[C(CH3)CF3]2-(CH2)4-、-(CH2)6-[C(CH3)CF3]2-(CH2)2-、-(CH2)6-[C(CH3)CF3]2-(CH2)3-、-(CH2)6-[C(CH3)CF3]2-(CH2)4-、 -[C(CH3)CF3]3-(CH2)-、-(CH2)-[C(CH3)CF3]3-、-(CH2)-[C(CH3)CF3]3-(CH2)-、-(CH2)-[C(CH3)CF3]3-(CH2)2-、-(CH2)-[C(CH3)CF3]3-(CH2)3-、-(CH2)-[C(CH3)CF3]3-(CH2)4-、-(CH2)-[C(CH3)CF3]3-(CH2)5-、-(CH2)-[C(CH3)CF3]3-(CH2)6-、-(CH2)-[C(CH3)CF3]3-(CH2)7-、-(CH2)-[C(CH3)CF3]3-(CH2)8-、-(CH2)2-[C(CH3)CF3]3-(CH2)-、-(CH2)3-[C(CH3)CF3]3-(CH2)-、-(CH2)4-[C(CH3)CF3]3-(CH2)-、-(CH2)5-[C(CH3)CF3]3-(CH2)-、-(CH2)6-[C(CH3)CF3]3-(CH2)-、-(CH2)7-[C(CH3)CF3]3-(CH2)-、-(CH2)8-[C(CH3)CF3]3-(CH2)-、-(CH2)2-[C(CH3)CF3]3-(CH2)2-、-(CH2)3-[C(CH3)CF3]3-(CH2)3-、-(CH2)4-[C(CH3)CF3]3-(CH2)4-、-(CH2)2-[C(CH3)CF3]3-(CH2)3-、-(CH2)2-[C(CH3)CF3]3-(CH2)4-、-(CH2)2-[C(CH3)CF3]3-(CH2)5-、-(CH2)2-[C(CH3)CF3]3-(CH2)6-、-(CH2)2-[C(CH3)CF3]3-(CH2)7-、-(CH2)3-[C(CH3)CF3]3-(CH2)2-、-(CH2)3-[C(CH3)CF3]3-(CH2)4-、-(CH2)3-[C(CH3)CF3]3-(CH2)5-、-(CH2)3-[C(CH3)CF3]3-(CH2)6-、-(CH2)4-[C(CH3)CF3]3-(CH2)2-、-(CH2)4-[C(CH3)CF3]3-(CH2)3-、-(CH2)4-[C(CH3)CF3]3-(CH2)5-、-(CH2)5-[C(CH3)CF3]3-(CH2)2-、-(CH2)5-[C(CH3)CF3]3-(CH2)3-、-(CH2)5-[C(CH3)CF3]3-(CH2)4-、-(CH2)6-[C(CH3)CF3]3-(CH2)2-、-(CH2)6-[C(CH3)CF3]3-(CH2)3-、 -[C(CH3)CF3]4-(CH2)-、-(CH2)-[C(CH3)CF3]4-、-(CH2)-[C(CH3)CF3]4-(CH2)-、-(CH2)-[C(CH3)CF3]4-(CH2)2-、-(CH2)-[C(CH3)CF3]4-(CH2)3-、-(CH2)-[C(CH3)CF3]4-(CH2)4-、-(CH2)-[C(CH3)CF3]4-(CH2)5-、-(CH2)-[C(CH3)CF3]4-(CH2)6-、-(CH2)-[C(CH3)CF3]4-(CH2)7-、-(CH2)-[C(CH3)CF3]4-(CH2)8-、-(CH2)-[C(CH3)CF3]4-(CH2)9-、-(CH2)-[C(CH3)CF3]4-(CH2) 10-、-(CH2)2-[C(CH3)CF3]4-(CH2)-、-(CH2)3-[C(CH3)CF3]4-(CH2)-、-(CH2)4-[C(CH3)CF3]4-(CH2)-、-(CH2)5-[C(CH3)CF3]4-(CH2)-、-(CH2)6-[C(CH3)CF3]4-(CH2)-、-(CH2)7-[C(CH3)CF3]4-(CH2)-、-(CH2)2-[C(CH3)CF3]4-(CH2)2-、-(CH2)3-[C(CH3)CF3]4-(CH2)3-、-(CH2)4-[C(CH3)CF3]4-(CH2)4-、-(CH2)5-[C(CH3)CF3]4-(CH2)5-、-(CH2)2-[C(CH3)CF3]4-(CH2)3-、-(CH2)2-[C(CH3)CF3]4-(CH2)4-、-(CH2)2-[C(CH3)CF3]4-(CH2)5-、-(CH2)2-[C(CH3)CF3]4-(CH2)6-、-(CH2)3-[C(CH3)CF3]4-(CH2)2-、-(CH2)3-[C(CH3)CF3]4-(CH2)4-、-(CH2)4-[C(CH3)CF3]4-(CH2)2-、-(CH2)4-[C(CH3)CF3]4-(CH2)3-、-(CH2)5-[C(CH3)CF3]4-(CH2)2-、-(CH2)5-[C(CH3)CF3]4-(CH2)3-、-(CH2)6-[C(CH3)CF3]4-(CH2)2-、 -[C(CH3)CF3]5-(CH2)-、-(CH2)-[C(CH3)CF3]5-、-(CH2)-[C(CH3)CF3]5-(CH2)-、-(CH2)-[C(CH3)CF3]5-(CH2)2-、-(CH2)-[C(CH3)CF3]5-(CH2)3-、-(CH2)-[C(CH3)CF3]5-(CH2)4-、-(CH2)-[C(CH3)CF3]5-(CH2)5-、-(CH2)-[C(CH3)CF3]5-(CH2)6-、-(CH2)2-[C(CH3)CF3]5-(CH2)-、-(CH2)3-[C(CH3)CF3]5-(CH2)-、-(CH2)4-[C(CH3)CF3]5-(CH2)-、-(CH2)5-[C(CH3)CF3]5-(CH2)-、-(CH2)6-[C(CH3)CF3]5-(CH2)-、-(CH2)2-[C(CH3)CF3]5-(CH2)2-、-(CH2)3-[C(CH3)CF3]5-(CH2)3-、-(CH2)4-[C(CH3)CF3]5-(CH2)4-、-(CH2)2-[C(CH3)CF3]5-(CH2)3-、-(CH2)2-[C(CH3)CF3]5-(CH2)4-、-(CH2)2-[C(CH3)CF3]5-(CH2)5-、-(CH2)2-[C(CH3)CF3]5-(CH2)6-、-(CH2)3-[C(CH3)CF3]5-(CH2)2-、-(CH2)3-[C(CH3)CF3]5-(CH2)4-、-(CH2)4-[C(CH3)CF3]5-(CH2)2-、-(CH2)4-[C(CH3)CF3]5-(CH2)3-、-(CH2)5-[C(CH3)CF3]5-(CH2)2-、 -[CH(CH2CF3)]-(CH2)-、-(CH2)-[CH(CH2CF3)]-、-(CH2)-[CH(CH2CF3)]-(CH2)-、-(CH2)-[CH(CH2CF3)]-(CH2)2-、-(CH2)-[CH(CH2CF3)]-(CH2)3-、-(CH2)-[CH(CH2CF3)]-(CH2)4-、-(CH2)-[CH(CH2CF3)]-(CH2)5-、-(CH2)-[CH(CH2CF3)]-(CH2)6-、-(CH2)-[CH(CH2CF3)]-(CH2)7-、-(CH2)-[CH(CH2CF3)]-(CH2)8-、-(CH2)-[CH(CH2CF3)]-(CH2)9-、-(CH2)-[CH(CH2CF3)]-(CH2) 10 -、-(CH2)2-[CH(CH2CF3)]-(CH2)-、-(CH2)3-[CH(CH2CF3)]-(CH2)-、-(CH2)4-[CH(CH2CF3)]-(CH2)-、-(CH2)5-[CH(CH2CF3)]-(CH2)-、-(CH2)6-[CH(CH2CF3)]-(CH2)-、-(CH2)7-[CH(CH2CF3)]-(CH2)-、-(CH2)8-[CH(CH2CF3)]-(CH2)-、-(CH2)9-[CH(CH2CF3)]-(CH2)-、-(CH2) 10-[CH(CH2CF3)]-(CH2)-、-(CH2)2-[CH(CH2CF3)]-(CH2)2-、-(CH2)3-[CH(CH2CF3)]-(CH2)3-、-(CH2)4-[CH(CH2CF3)]-(CH2)4-、-(CH2)5-[CH(CH2CF3)]-(CH2)5-、-(CH2)2-[CH(CH2CF3)]-(CH2)3-、-(CH2)2-[CH(CH2CF3)]-(CH2)4-、-(CH2)2-[CH(CH2CF3)]-(CH2)5-、-(CH2)2-[CH(CH2CF3)]-(CH2)6-、-(CH2)2-[CH(CH2CF3)]-(CH2)7-、-(CH2)2-[CH(CH2CF3)]-(CH2)8-、-(CH2)2-[CH(CH2CF3)]-(CH2)9-、-(CH2)3-[CH(CH2CF3)]-(CH2)2-、-(CH2)3-[CH(CH2CF3)]-(CH2)4-、-(CH2)3-[CH(CH2CF3)]-(CH2)5-、-(CH2)3-[CH(CH2CF3)]-(CH2)6-、-(CH2)3-[CH(CH2CF3)]-(CH2)7-、-(CH2)3-[CH(CH2CF3)]-(CH2)8-、-(CH2)4-[CH(CH2CF3)]-(CH2)2-、-(CH2)4-[CH(CH2CF3)]-(CH2)3-、-(CH2)4-[CH(CH2CF3)]-(CH2)5-、-(CH2)4-[CH(CH2CF3)]-(CH2)6-、-(CH2)4-[CH(CH2CF3)]-(CH2)7-、-(CH2)5-[CH(CH2CF3)]-(CH2)2-、-(CH2)5-[CH(CH2CF3)]-(CH2)3-、-(CH2)5-[CH(CH2CF3)]-(CH2)4-、-(CH2)5-[CH(CH2CF3)]-(CH2)6-、-(CH2)6-[CH(CH2CF3)]-(CH2)2-、-(CH2)6-[CH(CH2CF3)]-(CH2)3-、-(CH2)6-[CH(CH2CF3)]-(CH2)4-、-(CH2)6-[CH(CH2CF3)]-(CH2)5-、 -[CH(CH2CF3)]2-(CH2)-、-(CH2)-[CH(CH2CF3)]2-、-(CH2)-[CH(CH2CF3)]2-(CH2)-、-(CH2)-[CH(CH2CF3)]2-(CH2)2-、-(CH2)-[CH(CH2CF3)]2-(CH2)3-、-(CH2)-[CH(CH2CF3)]2-(CH2)4-、-(CH2)-[CH(CH2CF3)]2-(CH2)5-、-(CH2)-[CH(CH2CF3)]2-(CH2)6-、-(CH2)-[CH(CH2CF3)]2-(CH2)7-、-(CH2)-[CH(CH2CF3)]2-(CH2)8-、-(CH2)-[CH(CH2CF3)]2-(CH2)9-、-(CH2)2-[CH(CH2CF3)]2-(CH2)-、-(CH2)3-[CH(CH2CF3)]2-(CH2)-、-(CH2)4-[CH(CH2CF3)]2-(CH2)-、-(CH2)5-[CH(CH2CF3)]2-(CH2)-、-(CH2)6-[CH(CH2CF3)]2-(CH2)-、-(CH2)7-[CH(CH2CF3)]2-(CH2)-、-(CH2)8-[CH(CH2CF3)]2-(CH2)-、-(CH2)9-[CH(CH2CF3)]2-(CH2)-、-(CH2)2-[CH(CH2CF3)]2-(CH2)2-、-(CH2)3-[CH(CH2CF3)]2-(CH2)3-、-(CH2)4-[CH(CH2CF3)]2-(CH2)4-、-(CH2)5-[CH(CH2CF3)]2-(CH2)5-、-(CH2)2-[CH(CH2CF3)]2-(CH2)3-、-(CH2)2-[CH(CH2CF3)]2-(CH2)4-、-(CH2)2-[CH(CH2CF3)]2-(CH2)5-、-(CH2)2-[CH(CH2CF3)]2-(CH2)6-、-(CH2)2-[CH(CH2CF3)]2-(CH2)7-、-(CH2)2-[CH(CH2CF3)]2-(CH2)8-、-(CH2)3-[CH(CH2CF3)]2-(CH2)2-、-(CH2)3-[CH(CH2CF3)]2-(CH2)4-、-(CH2)3-[CH(CH2CF3)]2-(CH2)5-、-(CH2)3-[CH(CH2CF3)]2-(CH2)6-、-(CH2)3-[CH(CH2CF3)]2-(CH2)7-、-(CH2)4-[CH(CH2CF3)]2-(CH2)2-、-(CH2)4-[CH(CH2CF3)]2-(CH2)3-、-(CH2)4-[CH(CH2CF3)]2-(CH2)5-、-(CH2)4-[CH(CH2CF3)]2-(CH2)6-、-(CH2)5-[CH(CH2CF3)]2-(CH2)2-、-(CH2)5-[CH(CH2CF3)]2-(CH2)3-、-(CH2)5-[CH(CH2CF3)]2-(CH2)4-、-(CH2)6-[CH(CH2CF3)]2-(CH2)2-、-(CH2)6-[CH(CH2CF3)]2-(CH2)3-、-(CH2)6-[CH(CH2CF3)]2-(CH2)4-、 -[CH(CH2CF3)]3-(CH2)-、-(CH2)-[CH(CH2CF3)]3-、-(CH2)-[CH(CH2CF3)]3-(CH2)-、-(CH2)-[CH(CH2CF3)]3-(CH2)2-、-(CH2)-[CH(CH2CF3)]3-(CH2)3-、-(CH2)-[CH(CH2CF3)]3-(CH2)4-、-(CH2)-[CH(CH2CF3)]3-(CH2)5-、-(CH2)-[CH(CH2CF3)]3-(CH2)6-、-(CH2)-[CH(CH2CF3)]3-(CH2)7-、-(CH2)-[CH(CH2CF3)]3-(CH2)8-、-(CH2)2-[CH(CH2CF3)]3-(CH2)-、-(CH2)3-[CH(CH2CF3)]3-(CH2)-、-(CH2)4-[CH(CH2CF3)]3-(CH2)-、-(CH2)5-[CH(CH2CF3)]3-(CH2)-、-(CH2)6-[CH(CH2CF3)]3-(CH2)-、-(CH2)7-[CH(CH2CF3)]3-(CH2)-、-(CH2)8-[CH(CH2CF3)]3-(CH2)-、-(CH2)2-[CH(CH2CF3)]3-(CH2)2-、-(CH2)3-[CH(CH2CF3)]3-(CH2)3-、-(CH2)4-[CH(CH2CF3)]3-(CH2)4-、-(CH2)2-[CH(CH2CF3)]3-(CH2)3-、-(CH2)2-[CH(CH2CF3)]3-(CH2)4-、-(CH2)2-[CH(CH2CF3)]3-(CH2)5-、-(CH2)2-[CH(CH2CF3)]3-(CH2)6-、-(CH2)2-[CH(CH2CF3)]3-(CH2)7-、-(CH2)3-[CH(CH2CF3)]3-(CH2)2-、-(CH2)3-[CH(CH2CF3)]3-(CH2)4-、-(CH2)3-[CH(CH2CF3)]3-(CH2)5-、-(CH2)3-[CH(CH2CF3)]3-(CH2)6-、-(CH2)4-[CH(CH2CF3)]3-(CH2)2-、-(CH2)4-[CH(CH2CF3)]3-(CH2)3-、-(CH2)4-[CH(CH2CF3)]3-(CH2)5-、-(CH2)5-[CH(CH2CF3)]3-(CH2)2-、-(CH2)5-[CH(CH2CF3)]3-(CH2)3-、-(CH2)5-[CH(CH2CF3)]3-(CH2)4-、-(CH2)6-[CH(CH2CF3)]3-(CH2)2-、-(CH2)6-[CH(CH2CF3)]3-(CH2)3-、 -[CH(CH2CF3)]4-(CH2)-、-(CH2)-[CH(CH2CF3)]4-、-(CH2)-[CH(CH2CF3)]4-(CH2)-、-(CH2)-[CH(CH2CF3)]4-(CH2)2-、-(CH2)-[CH(CH2CF3)]4-(CH2)3-、-(CH2)-[CH(CH2CF3)]4-(CH2)4-、-(CH2)-[CH(CH2CF3)]4-(CH2)5-、-(CH2)-[CH(CH2CF3)]4-(CH2)6-、-(CH2)-[CH(CH2CF3)]4-(CH2)7-、-(CH2)-[CH(CH2CF3)]4-(CH2)8-、-(CH2)-[CH(CH2CF3)]4-(CH2)9-、-(CH2)-[CH(CH2CF3)]4-(CH2) 10-、-(CH2)2-[CH(CH2CF3)]4-(CH2)-、-(CH2)3-[CH(CH2CF3)]4-(CH2)-、-(CH2)4-[CH(CH2CF3)]4-(CH2)-、-(CH2)5-[CH(CH2CF3)]4-(CH2)-、-(CH2)6-[CH(CH2CF3)]4-(CH2)-、-(CH2)7-[CH(CH2CF3)]4-(CH2)-、-(CH2)2-[CH(CH2CF3)]4-(CH2)2-、-(CH2)3-[CH(CH2CF3)]4-(CH2)3-、-(CH2)4-[CH(CH2CF3)]4-(CH2)4-、-(CH2)5-[CH(CH2CF3)]4-(CH2)5-、-(CH2)2-[CH(CH2CF3)]4-(CH2)3-、-(CH2)2-[CH(CH2CF3)]4-(CH2)4-、-(CH2)2-[CH(CH2CF3)]4-(CH2)5-、-(CH2)2-[CH(CH2CF3)]4-(CH2)6-、-(CH2)3-[CH(CH2CF3)]4-(CH2)2-、-(CH2)3-[CH(CH2CF3)]4-(CH2)4-、-(CH2)4-[CH(CH2CF3)]4-(CH2)2-、-(CH2)4-[CH(CH2CF3)]4-(CH2)3-、-(CH2)5-[CH(CH2CF3)]4-(CH2)2-、-(CH2)5-[CH(CH2CF3)]4-(CH2)3-、-(CH2)6-[CH(CH2CF3)]4-(CH2)2-、 -[CH(CH2CF3)]5-(CH2)-、-(CH2)-[CH(CH2CF3)5-、-(CH2)-[CH(CH2CF3)]5-(CH2)-、-(CH2)-[CH(CH2CF3)]5-(CH2)2-、-(CH2)-[CH(CH2CF3)]5-(CH2)3-、-(CH2)-[CH(CH2CF3)]5-(CH2)4-、-(CH2)-[CH(CH2CF3)]5-(CH2)5-、-(CH2)-[CH(CH2CF3)]5-(CH2)6-、-(CH2)2-[CH(CH2CF3)]5-(CH2)-、-(CH2)3-[CH(CH2CF3)]5-(CH2)-、-(CH2)4-[CH(CH2CF3)]5-(CH2)-、-(CH2)5-[CH(CH2CF3)]5-(CH2)-、-(CH2)6-[CH(CH2CF3)]5-(CH2)-、-(CH2)2-[CH(CH2CF3)]5-(CH2)2-、-(CH2)3-[CH(CH2CF3)]5-(CH2)3-、-(CH2)4-[CH(CH2CF3)]5-(CH2)4-、-(CH2)2-[CH(CH2CF3)]5-(CH2)3-、-(CH2)2-[CH(CH2CF3)]5-(CH2)4-、-(CH2)2-[CH(CH2CF3)]5-(CH2)5-、-(CH2)2-[CH(CH2CF3)]5-(CH2)6-、-(CH2)3-[CH(CH2CF3)]5-(CH2)2-、-(CH2)3-[CH(CH2CF3)]5-(CH2)4-、-(CH2)4-[CH(CH2CF3)]5-(CH2)2-、-(CH2)4-[CH(CH2CF3)]5-(CH2)3-、-(CH2)5-[CH(CH2CF3)]5-(CH2)2-、 -[C(CH3)(CH2CF3)]-(CH2)-、-(CH2)-[C(CH3)(CH2CF3)]-、-(CH2)-[C(CH3)(CH2CF3)]-(CH2)-、-(CH2)-[C(CH3)(CH2CF3)]-(CH2)2-、-(CH2)-[C(CH3)(CH2CF3)]-(CH2)3-、-(CH2)-[C(CH3)(CH2CF3)]-(CH2)4-、-(CH2)-[C(CH3)(CH2CF3)]-(CH2)5-、-(CH2)-[C(CH3)(CH2CF3)]-(CH2)6-、-(CH2)-[C(CH3)(CH2CF3)]-(CH2)7-、-(CH2)-[C(CH3)(CH2CF3)]-(CH2)8-、-(CH2)-[C(CH3)(CH2CF3)]-(CH2)9-、-(CH2)-[C(CH3)(CH2CF3)]-(CH2) 10 -、-(CH2)2-[C(CH3)(CH2CF3)]-(CH2)-、-(CH2)3-[C(CH3)(CH2CF3)]-(CH2)-、-(CH2)4-[C(CH3)(CH2CF3)]-(CH2)-、-(CH2)5-[C(CH3)(CH2CF3)]-(CH2)-、-(CH2)6-[C(CH3)(CH2CF3)]-(CH2)-、-(CH2)7-[C(CH3)(CH2CF3)]-(CH2)-、-(CH2)8-[C(CH3)(CH2CF3)]-(CH2)-、-(CH2)9-[C(CH3)(CH2CF3)]-(CH2)-、-(CH2) 10-[C(CH3)(CH2CF3)]-(CH2)-、-(CH2)2-[C(CH3)(CH2CF3)]-(CH2)2-、-(CH2)3-[C(CH3)(CH2CF3)]-(CH2)3-、-(CH2)4-[C(CH3)(CH2CF3)]-(CH2)4-、-(CH2)5-[C(CH3)(CH2CF3)]-(CH2)5-、-(CH2)2-[C(CH3)(CH2CF3)]-(CH2)3-、-(CH2)2-[C(CH3)(CH2CF3)]-(CH2)4-、-(CH2)2-[C(CH3)(CH2CF3)]-(CH2)5-、-(CH2)2-[C(CH3)(CH2CF3)]-(CH2)6-、-(CH2)2-[C(CH3)(CH2CF3)]-(CH2)7-、-(CH2)2-[C(CH3)(CH2CF3)]-(CH2)8-、-(CH2)2-[C(CH3)(CH2CF3)]-(CH2)9-、-(CH2)3-[C(CH3)(CH2CF3)]-(CH2)2-、-(CH2)3-[C(CH3)(CH2CF3)]-(CH2)4-、-(CH2)3-[C(CH3)(CH2CF3)]-(CH2)5-、-(CH2)3-[C(CH3)(CH2CF3)]-(CH2)6-、-(CH2)3-[C(CH3)(CH2CF3)]-(CH2)7-、-(CH2)3-[C(CH3)(CH2CF3)]-(CH2)8-、-(CH2)4-[C(CH3)(CH2CF3)]-(CH2)2-、-(CH2)4-[C(CH3)(CH2CF3)]-(CH2)3-、-(CH2)4-[C(CH3)(CH2CF3)]-(CH2)5-、-(CH2)4-[C(CH3)(CH2CF3)]-(CH2)6-、-(CH2)4-[C(CH3)(CH2CF3)]-(CH2)7-、-(CH2)5-[C(CH3)(CH2CF3)]-(CH2)2-、-(CH2)5-[C(CH3)(CH2CF3)]-(CH2)3-、-(CH2)5-[C(CH3)(CH2CF3)]-(CH2)4-、-(CH2)5-[C(CH3)(CH2CF3)]-(CH2)6-、-(CH2)6-[C(CH3)(CH2CF3)]-(CH2)2-、-(CH2)6-[C(CH3)(CH2CF3)]-(CH2)3-、-(CH2)6-[C(CH3)(CH2CF3)]-(CH2)4-、-(CH2)6-[C(CH3)(CH2CF3)]-(CH2)5-、 -[C(CH3)(CH2CF3)]2-(CH2)-、-(CH2)-[C(CH3)(CH2CF3)]2-、-(CH2)-[C(CH3)(CH2CF3)]2-(CH2)-、-(CH2)-[C(CH3)(CH2CF3)]2-(CH2)2-、-(CH2)-[C(CH3)(CH2CF3)]2-(CH2)3-、-(CH2)-[C(CH3)(CH2CF3)]2-(CH2)4-、-(CH2)-[C(CH3)(CH2CF3)]2-(CH2)5-、-(CH2)-[C(CH3)(CH2CF3)]2-(CH2)6-、-(CH2)-[C(CH3)(CH2CF3)]2-(CH2)7-、-(CH2)-[C(CH3)(CH2CF3)]2-(CH2)8-、-(CH2)-[C(CH3)(CH2CF3)]2-(CH2)9-、-(CH2)2-[C(CH3)(CH2CF3)]2-(CH2)-、-(CH2)3-[C(CH3)(CH2CF3)]2-(CH2)-、-(CH2)4-[C(CH3)(CH2CF3)]2-(CH2)-、-(CH2)5-[C(CH3)(CH2CF3)]2-(CH2)-、-(CH2)6-[C(CH3)(CH2CF3)]2-(CH2)-、-(CH2)7-[C(CH3)(CH2CF3)]2-(CH2)-、-(CH2)8-[C(CH3)(CH2CF3)]2-(CH2)-、-(CH2)9-[C(CH3)(CH2CF3)]2-(CH2)-、-(CH2)2-[C(CH3)(CH2CF3)]2-(CH2)2-、-(CH2)3-[C(CH3)(CH2CF3)]2-(CH2)3-、-(CH2)4-[C(CH3)(CH2CF3)]2-(CH2)4-、-(CH2)5-[C(CH3)(CH2CF3)]2-(CH2)5-、-(CH2)2-[C(CH3)(CH2CF3)]2-(CH2)3-、-(CH2)2-[C(CH3)(CH2CF3)]2-(CH2)4-、-(CH2)2-[C(CH3)(CH2CF3)]2-(CH2)5-、-(CH2)2-[C(CH3)(CH2CF3)]2-(CH2)6-、-(CH2)2-[C(CH3)(CH2CF3)]2-(CH2)7-、-(CH2)2-[C(CH3)(CH2CF3)]2-(CH2)8-、-(CH2)3-[C(CH3)(CH2CF3)]2-(CH2)2-、-(CH2)3-[C(CH3)(CH2CF3)]2-(CH2)4-、-(CH2)3-[C(CH3)(CH2CF3)]2-(CH2)5-、-(CH2)3-[C(CH3)(CH2CF3)]2-(CH2)6-、-(CH2)3-[C(CH3)(CH2CF3)]2-(CH2)7-、-(CH2)4-[C(CH3)(CH2CF3)]2-(CH2)2-、-(CH2)4-[C(CH3)(CH2CF3)]2-(CH2)3-、-(CH2)4-[C(CH3)(CH2CF3)]2-(CH2)5-、-(CH2)4-[C(CH3)(CH2CF3)]2-(CH2)6-、-(CH2)5-[C(CH3)(CH2CF3)]2-(CH2)2-、-(CH2)5-[C(CH3)(CH2CF3)]2-(CH2)3-、-(CH2)5-[C(CH3)(CH2CF3)]2-(CH2)4-、-(CH2)6-[C(CH3)(CH2CF3)]2-(CH2)2-、-(CH2)6-[C(CH3)(CH2CF3)]2-(CH2)3-、-(CH2)6-[C(CH3)(CH2CF3)]2-(CH2)4-、 -[C(CH3)(CH2CF3)]3-(CH2)-、-(CH2)-[C(CH3)(CH2CF3)]3-、-(CH2)-[C(CH3)(CH2CF3)]3-(CH2)-、-(CH2)-[C(CH3)(CH2CF3)]3-(CH2)2-、-(CH2)-[C(CH3)(CH2CF3)]3-(CH2)3-、-(CH2)-[C(CH3)(CH2CF3)]3-(CH2)4-、-(CH2)-[C(CH3)(CH2CF3)]3-(CH2)5-、-(CH2)-[C(CH3)(CH2CF3)]3-(CH2)6-、-(CH2)-[C(CH3)(CH2CF3)]3-(CH2)7-、-(CH2)-[C(CH3)(CH2CF3)]3-(CH2)8-、-(CH2)2-[C(CH3)(CH2CF3)]3-(CH2)-、-(CH2)3-[C(CH3)(CH2CF3)]3-(CH2)-、-(CH2)4-[C(CH3)(CH2CF3)]3-(CH2)-、-(CH2)5-[C(CH3)(CH2CF3)]3-(CH2)-、-(CH2)6-[C(CH3)(CH2CF3)]3-(CH2)-、-(CH2)7-[C(CH3)(CH2CF3)]3-(CH2)-、-(CH2)8-[C(CH3)(CH2CF3)]3-(CH2)-、-(CH2)2-[C(CH3)(CH2CF3)]3-(CH2)2-、-(CH2)3-[C(CH3)(CH2CF3)]3-(CH2)3-、-(CH2)4-[C(CH3)(CH2CF3)]3-(CH2)4-、-(CH2)2-[C(CH3)(CH2CF3)]3-(CH2)3-、-(CH2)2-[C(CH3)(CH2CF3)]3-(CH2)4-、-(CH2)2-[C(CH3)(CH2CF3)]3-(CH2)5-、-(CH2)2-[C(CH3)(CH2CF3)]3-(CH2)6-、-(CH2)2-[C(CH3)(CH2CF3)]3-(CH2)7-、-(CH2)3-[C(CH3)(CH2CF3)]3-(CH2)2-、-(CH2)3-[C(CH3)(CH2CF3)]3-(CH2)4-、-(CH2)3-[C(CH3)(CH2CF3)]3-(CH2)5-、-(CH2)3-[C(CH3)(CH2CF3)]3-(CH2)6-、-(CH2)4-[C(CH3)(CH2CF3)]3-(CH2)2-、-(CH2)4-[C(CH3)(CH2CF3)]3-(CH2)3-、-(CH2)4-[C(CH3)(CH2CF3)]3-(CH2)5-、-(CH2)5-[C(CH3)(CH2CF3)]3-(CH2)2-、-(CH2)5-[C(CH3)(CH2CF3)]3-(CH2)3-、-(CH2)5-[C(CH3)(CH2CF3)]3-(CH2)4-、-(CH2)6-[C(CH3)(CH2CF3)]3-(CH2)2-、-(CH2)6-[C(CH3)(CH2CF3)]3-(CH2)3-、 -[C(CH3)(CH2CF3)]4-(CH2)-、-(CH2)-[C(CH3)(CH2CF3)]4-、-(CH2)-[C(CH3)(CH2CF3)]4-(CH2)-、-(CH2)-[C(CH3)(CH2CF3)]4-(CH2)2-、-(CH2)-[C(CH3)(CH2CF3)]4-(CH2)3-、-(CH2)-[C(CH3)(CH2CF3)]4-(CH2)4-、-(CH2)-[C(CH3)(CH2CF3)]4-(CH2)5-、-(CH2)-[C(CH3)(CH2CF3)]4-(CH2)6-、-(CH2)-[C(CH3)(CH2CF3)]4-(CH2)7-、-(CH2)-[C(CH3)(CH2CF3)]4-(CH2)8-、-(CH2)-[C(CH3)(CH2CF3)]4-(CH2)9-、-(CH2)-[C(CH3)(CH2CF3)]4-(CH2) 10-、-(CH2)2-[C(CH3)(CH2CF3)]4-(CH2)-、-(CH2)3-[C(CH3)(CH2CF3)]4-(CH2)-、-(CH2)4-[C(CH3)(CH2CF3)]4-(CH2)-、-(CH2)5-[C(CH3)(CH2CF3)]4-(CH2)-、-(CH2)6-[C(CH3)(CH2CF3)]4-(CH2)-、-(CH2)7-[C(CH3)(CH2CF3)]4-(CH2)-、-(CH2)2-[C(CH3)(CH2CF3)]4-(CH2)2-、-(CH2)3-[C(CH3)(CH2CF3)]4-(CH2)3-、-(CH2)4-[C(CH3)(CH2CF3)]4-(CH2)4-、-(CH2)5-[C(CH3)(CH2CF3)]4-(CH2)5-、-(CH2)2-[C(CH3)(CH2CF3)]4-(CH2)3-、-(CH2)2-[C(CH3)(CH2CF3)]4-(CH2)4-、-(CH2)2-[C(CH3)(CH2CF3)]4-(CH2)5-、-(CH2)2-[C(CH3)(CH2CF3)]4-(CH2)6-、-(CH2)3-[C(CH3)(CH2CF3)]4-(CH2)2-、-(CH2)3-[C(CH3)(CH2CF3)]4-(CH2)4-、-(CH2)4-[C(CH3)(CH2CF3)]4-(CH2)2-、-(CH2)4-[C(CH3)(CH2CF3)]4-(CH2)3-、-(CH2)5-[C(CH3)(CH2CF3)]4-(CH2)2-、-(CH2)5-[C(CH3)(CH2CF3)]4-(CH2)3-、-(CH2)6-[C(CH3)(CH2CF3)]4-(CH2)2-、 -[C(CH3)(CH2CF3)]5-(CH2)-、-(CH2)-[C(CH3)(CH2CF3)]5-、-(CH2)-[C(CH3)(CH2CF3)]5-(CH2)-、-(CH2)-[C(CH3)(CH2CF3)]5-(CH2)2-、-(CH2)-[C(CH3)(CH2CF3)]5-(CH2)3-、-(CH2)-[C(CH3)(CH2CF3)]5-(CH2)4-、-(CH2)-[C(CH3)(CH2CF3)]5-(CH2)5-、-(CH2)-[C(CH3)(CH2CF3)]5-(CH2)6-、-(CH2)2-[C(CH3)(CH2CF3)]5-(CH2)-、-(CH2)3-[C(CH3)(CH2CF3)]5-(CH2)-、-(CH2)4-[C(CH3)(CH2CF3)]5-(CH2)-、-(CH2)5-[C(CH3)(CH2CF3)]5-(CH2)-、-(CH2)6-[C(CH3)(CH2CF3)]5-(CH2)-、-(CH2)2-[C(CH3)(CH2CF3)]5-(CH2)2-、-(CH2)3-[C(CH3)(CH2CF3)]5-(CH2)3-、-(CH2)4-[C(CH3)(CH2CF3)]5-(CH2)4-、-(CH2)2-[C(CH3)(CH2CF3)]5-(CH2)3-、-(CH2)2-[C(CH3)(CH2CF3)]5-(CH2)4-、-(CH2)2-[C(CH3)(CH2CF3)]5-(CH2)5-、-(CH2)2-[C(CH3)(CH2CF3)]5-(CH2)6-、-(CH2)3-[C(CH3)(CH2CF3)]5-(CH2)2-、-(CH2)3-[C(CH3)(CH2CF3)]5-(CH2)4-、-(CH2)4-[C(CH3)(CH2CF3)]5-(CH2)2-、-(CH2)4-[C(CH3)(CH2CF3)]5-(CH2)3-、-(CH2)5-[C(CH3)(CH2CF3)]5-(CH2)2-、 -(CH2)2-(CF2)-O-(CF2)-(CH2)2-、-(CH2)2-(CF2)-O-(CH2)-O-(CF2)-(CH2)2-、-(CH2)2-(CF2)-O-(CH2)2-O-(CF2)-(CH2)2、 -(CH2)-(CF2)-O-(CF2)-O-(CF2)-(CH2)-、-(CH2)2-(CF2)-O-(CF2)-O-(CF2)-(CH2)2-、-(CH2)3-(CF2)-O-(CF2)-O-(CF2)-(CH2)3-、-(CH2)4-(CF2)-O-(CF2)-O-(CF2)-(CH2)4-、-(CH2)-(CF2)-O-(CF2)-O-(CF2)-(CH2)2-、-(CH2)-(CF2)-O-(CF2)-O-(CF2)-(CH2)3-、-(CH2)-(CF2)-O-(CF2)-O-(CF2)-(CH2)4-、-(CH2)-(CF2)-O-(CF2)-O-(CF2)-(CH2)5-、-(CH2)-(CF2)-O-(CF2)-O-(CF2)-(CH2)6-、-(CH2)-(CF2)-O-(CF2)-O-(CF2)-(CH2)7-、-(CH2)2-(CF2)-O-(CF2)-O-(CF2)-(CH2)-、-(CH2)3-(CF2)-O-(CF2)-O-(CF2)-(CH2)-、-(CH2)4-(CF2)-O-(CF2)-O-(CF2)-(CH2)-、-(CH2)5-(CF2)-O-(CF2)-O-(CF2)-(CH2)-、-(CH2)6-(CF2)-O-(CF2)-O-(CF2)-(CH2)-、-(CH2)7-(CF2)-O-(CF2)-O-(CF2)-(CH2)-、-(CH2)2-(CF2)-O-(CF2)-O-(CF2)-(CH2)3-、-(CH2)2-(CF2)-O-(CF2)-O-(CF2)-(CH2)4-、-(CH2)2-(CF2)-O-(CF2)-O-(CF2)-(CH2)5-、-(CH2)2-(CF2)-O-(CF2)-O-(CF2)-(CH2)6-、-(CH2)3-(CF2)-O-(CF2)-O-(CF2)-(CH2)2-、-(CH2)4-(CF2)-O-(CF2)-O-(CF2)-(CH2)2-、-(CH2)5-(CF2)-O-(CF2)-O-(CF2)-(CH2)2-、-(CH2)6-(CF2)-O-(CF2)-O-(CF2)-(CH2)2-、-(CH2)3-(CF2)-O-(CF2)-O-(CF2)-(CH2)4-、-(CH2)4-(CF2)-O-(CF2)-O-(CF2)-(CH2)3-、-(CH2)3-(CF2)-O-(CF2)-O-(CF2)-(CH2)5-、-(CH2)5-(CF2)-O-(CF2)-O-(CF2)-(CH2)3-、 -(CH2)-(CF2)-O-(CF2)2-O-(CF2)-(CH2)-、-(CH2)2-(CF2)-O-(CF2)2-O-(CF2)-(CH2)2-、-(CH2)3-(CF2)-O-(CF2)2-O-(CF2)-(CH2)3-、-(CH2)4-(CF2)-O-(CF2)2-O-(CF2)-(CH2)4-、-(CH2)-(CF2)-O-(CF2)2-O-(CF2)-(CH2)2-、-(CH2)-(CF2)-O-(CF2)2-O-(CF2)-(CH2)3-、-(CH2)-(CF2)-O-(CF2)2-O-(CF2)-(CH2)4-、-(CH2)-(CF2)-O-(CF2)2-O-(CF2)-(CH2)5-、-(CH2)-(CF2)-O-(CF2)2-O-(CF2)-(CH2)6-、-(CH2)-(CF2)-O-(CF2)2-O-(CF2)-(CH2)7-、-(CH2)2-(CF2)-O-(CF2)2-O-(CF2)-(CH2)-、-(CH2)3-(CF2)-O-(CF2)2-O-(CF2)-(CH2)-、-(CH2)4-(CF2)-O-(CF2)2-O-(CF2)-(CH2)-、-(CH2)5-(CF2)-O-(CF2)2-O-(CF2)-(CH2)-、-(CH2)6-(CF2)-O-(CF2)2-O-(CF2)-(CH2)-、-(CH2)7-(CF2)-O-(CF2)2-O-(CF2)-(CH2)-、-(CH2)2-(CF2)-O-(CF2)2-O-(CF2)-(CH2)3-、-(CH2)2-(CF2)-O-(CF2)2-O-(CF2)-(CH2)4-、-(CH2)2-(CF2)-O-(CF2)2-O-(CF2)-(CH2)5-、-(CH2)2-(CF2)-O-(CF2)2-O-(CF2)-(CH2)6-、-(CH2)3-(CF2)-O-(CF2)2-O-(CF2)-(CH2)2-、-(CH2)4-(CF2)-O-(CF2)2-O-(CF2)-(CH2)2-、-(CH2)5-(CF2)-O-(CF2)2-O-(CF2)-(CH2)2-、-(CH2)6-(CF2)-O-(CF2)2-O-(CF2)-(CH2)2-、-(CH2)3-(CF2)-O-(CF2)2-O-(CF2)-(CH2)4-、-(CH2)4-(CF2)-O-(CF2)2-O-(CF2)-(CH2)3-、-(CH2)3-(CF2)-O-(CF2)2-O-(CF2)-(CH2)5-、-(CH2)5-(CF2)-O-(CF2)2-O-(CF2)-(CH2)3-、 -(CH2)-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)-、-(CH2)2-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)2-、-(CH2)3-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)3-、-(CH2)4-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)4-、-(CH2)-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)2-、-(CH2)-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)3-、-(CH2)-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)3-、-(CH2)-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)4-、-(CH2)-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)5-、-(CH2)-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)6-、-(CH2)-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)7-、-(CH2)2-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)-、-(CH2)3-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)-、-(CH2)4-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)-、-(CH2)5-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)-、-(CH2)6-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)-、-(CH2)7-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)-、-(CH2)2-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)3-、-(CH2)2-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)4-、-(CH2)2-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)5-、-(CH2)2-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)6-、-(CH2)3-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)2-、-(CH2)4-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)2-、-(CH2)5-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)2-、-(CH2)6-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)2-、-(CH2)3-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)4-、-(CH2)4-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)3-、-(CH2)3-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)5-、-(CH2)5-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)3-、 -(CH2)-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)-、-(CH2)2-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)2-、-(CH2)3-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)3-、-(CH2)4-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)4-、-(CH2)-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)2-、-(CH2)-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)3-、-(CH2)-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)4-、-(CH2)-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)5-、-(CH2)-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)6-、-(CH2)-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)7-、-(CH2)2-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)-、-(CH2)3-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)-、-(CH2)4-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)-、-(CH2)5-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)-、-(CH2)6-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)-、-(CH2)7-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)-、-(CH2)2-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)3-、-(CH2)2-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)4-、-(CH2)2-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)5-、-(CH2)2-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)6-、-(CH2)3-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)2-、-(CH2)4-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)2-、-(CH2)5-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)2-、-(CH2)6-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)2-、-(CH2)3-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)4-、-(CH2)4-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)3-、-(CH2)3-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)5-、-(CH2)5-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)3-、 -(CH2)-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)-、-(CH2)2-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)2-、-(CH2)3-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)3-、-(CH2)4-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)4-、-(CH2)-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)2-、-(CH2)-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)3-、-(CH2)-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)4-、-(CH2)-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)5-、-(CH2)-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)6-、-(CH2)-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)7-、-(CH2)2-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)-、-(CH2)3-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)-、-(CH2)4-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)-、-(CH2)5-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)-、-(CH2)6-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)-、-(CH2)7-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)-、-(CH2)2-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)3-、-(CH2)2-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)4-、-(CH2)2-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)5-、-(CH2)2-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)6-、-(CH2)3-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)2-, -(CH2)4-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)2-, -(CH2)5-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)2-, -(CH2)6-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)2-, -(CH2)3-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)4-, -(CH2)4-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)3-, -(CH2)3-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)5-, -(CH2)5-(CF2)2-O-(CF2)2-O-(CF2)2-O-(CF2)2-(CH2)3-.

[0161] Preferred examples of -R2- according to the present invention are -(CH2)5-, -(CH2)6-, -(CH2)7-, -(CH2)8-, -(CH2)9-, -(CH2) 10 - 11 - 12 - 13-, -(CH2)2-S-(CH2)2-, -(CH2)2-SO2-(CH2)2-, -(CH2)2-S-(CH2)2-S-(CH2)2-, -(CH2)2-O-(CH2)2-O-(CH2)2-, -(CH2)2-S-(CH2)2-O-(CH2)2-, -(CH2)2-SO2-(CH2)2-O-(CH2)2-, -(CH2)2-SO2-(CH2)2-S-(CH2)2-, -(CH2)2-O-(CH2)2-O-(CH2)2-O-(CH2)2-, -(CH2)2-O-(CH2)2-S-(CH2)2-O-(CH2)2-, -(CH2)2-S-(CH2)2-O-(CH2)2-S-(CH2)2-, -(CH2)2-SO2-(CH2)2-O-(CH2)2-SO2-(CH2)2-, -(CH2)2-S-(CH2)2-S-(CH2)2-S-(CH2)2-, -(CH2)2-SO2-(CH2)2-S-(CH2)2-SO2-(CH2)2-, -(CH2)2-SO2-(CH2)2-SO2-(CH2)2-SO2-(CH2)2-, -(CH2)2-O-(CH2)2-SO2-(CH2)2-O-(CH2)2-, -(CH2)3-(CF2)-(CH2)3-, -(CH2)-(CF2)3-(CH2)-, -(CH2)2-(CF2)4-(CH2)2-, -(CH2)-[CH(CF3)]-(CH2)-, -(CH2)-[C(CH3)CF3]-(CH2)-, -(CH2)-[CH(CH2CF3)]-(CH2)-, -(CH2)-[C(CH3)(CH2CF3)]-(CH2)-, -(CH2)2-(CF2)-O-(CF2)-O-(CF2)-(CH2)2- and -(CH2)-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)-.

[0162] Particularly preferred examples of -R2- are, according to the present invention, -(CH2)5-, -(CH2)6-, -(CH2)7-, -(CH2)8-, -(CH2)9-, -(CH2) 10 -, -(CH2) 11 -, -(CH2) 12 -, -(CH2) 13-, -(CH2)2-S-(CH2)2-, -(CH2)2-SO2-(CH2)2-, -(CH2)2-S-(CH2)2-S-(CH2)2-, -(C H2)2-O-(CH2)2-O-(CH2)2-, -(CH2)2-O-(CH2)2-O-(CH2)2-O-(CH2)2-, -(CH2)2-O- (CH2)2-S-(CH2)2-O-(CH2)2-, -(CH2)2-S-(CH2)2-O-(CH2)2-S-(CH2)2-, -(CH2)2- S-(CH2)2-S-(CH2)2-S-(CH2)2- and -(CH2)2-SO2-(CH2)2-S-(CH2)2-SO2-(CH2)2.

[0163] The substituent -R2- in at least one linking element Y-R2- or N-R2-R1 is -(C(R)2) o -, preference is given to compounds of the formula (I), (I#), (I'), (I'-a), (I'-b), (I'-c), (I'-d), (I'-e), (I'-f), (I'-g), (I'-h), (I'-i) and (I'') having the substituents as described above or preferably as described above, with a polymerizable group as described above or preferably as described below, wherein R and o have the meanings as described above or preferably as described below.

[0164] Thus, the substituent -R2- in at least one linking element Y-R2- or N-R2-R1 is -(C(R)2) o -, the monomers of formula (I), (I#), (I'), (I'-a), (I'-b), (I'-c), (I'-d), (I'-e), (I'-f), (I'-g), (I'-h), (I'-i) and (I'') are preferred for preparing the above-described ophthalmic devices or precursor articles for producing ophthalmic devices, having the polymerizable groups as described above or preferably as described above or below, as described above or preferably as having the substituents as described above, where R and o have the meanings as described or preferably as described above. Such ophthalmic devices and precursor articles prepared using these monomers are particularly preferred.

[0165] Particularly preferred examples of -R2- are -(CH2)8-, -(CH2)9-, -(CH2) 10 -, -(CH2) 11 - and -(CH2) 12 Very particularly preferably, -R2 according to the invention is -(CH2) 12 is.

[0166] Accordingly, the present invention further relates to an ophthalmic device or a precursor article for producing an ophthalmic device comprising a polymerized compound of Formula (I), Formula (I#), Formula (I'), Formula (I'-a), Formula (I'-b), Formula (I'-c), Formula (I'-d), Formula (I'-e), Formula (I'-f), Formula (I'-g), Formula (I'-h), Formula (I'-i), and Formula (I''), as described above, or preferably as described above, wherein -R2- is, independently in each occurrence, -(C(R)2) o -, where R and o have the meanings as described or preferably as previously stated.

[0167] Accordingly, the present invention relates to compounds of formula (I), formula (I#), formula (I'), formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h), formula (I'-i), and formula (I''), as described above, or preferably as described above, wherein -R2- is independently in each occurrence -(C(R)2) o -, wherein R and o have the meanings as described or preferably as previously stated, taking into account the disclosed provisos.

[0168] The substituent Y-R2- in formula (I), formula (I#), formula (I'), formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h), formula (I'-i), and formula (I'') is selected from the group consisting of O-R2-, -R2-, wherein Y is a bond, SO2-R2-, and S-R2-; 、 In the formula, -R2 has the meaning given above or preferably or particularly preferably has the meaning given above.

[0169] The substituent Y-R2- is preferably selected from the group consisting of O-R2- and -R2-, where Y is a bond and -R2 has the meanings given above or preferably or particularly preferably given above.

[0170] The substituent Y-R2-R1 in the formula (I), formula (I#), formula (I'), formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h), formula (I'-i), and formula (I'') is O-R2-R1, -R2-R 1、 selected from the group consisting of SO2-R2-R1 and S-R2-R1, or preferably selected from the group consisting of O-R2-R1 and -R2-R1, where -R2- has the meanings given above or preferably or particularly preferably has the meanings given above, and R1 is trimethoxysilyl, triethoxysilyl, dimethoxymethylsilyl, diethoxymethylsilyl or a polymerizable group according to formula (4),

[0171] [ka] During the ceremony, X 11 is selected from the group consisting of O, S, O-SO2, SO2-O, C(=O), OC(=O), C(=O)O, S(C=O), and (C=O)S; R5, R6, and R7, in each occurrence, are independently selected from the group consisting of H, F, a linear or branched non-fluorinated, partially fluorinated, or fully fluorinated alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 14 carbon atoms; c is 0 or 1.

[0172] The substituent N-R2-R1 in the formulae (I), (I#), (I'), (I'-a), (I'-b), (I'-c), (I'-d), (I'-e), (I'-f), (I'-g), (I'-h), (I'-i) and (I'') is preferred, in which -R2 has the meaning as defined above or preferably as defined above, and R1 is trimethoxysilyl, triethoxysilyl, dimethoxymethylsilyl, diethoxymethylsilyl or a polymerizable group according to formula (4),

[0173] [ka] During the ceremony, X 11 is selected from the group consisting of O, S, O-SO2, SO2-O, C(=O), OC(=O), C(=O)O, S(C=O), and (C=O)S; R5, R6, and R7, in each occurrence, are independently selected from the group consisting of H, F, a linear or branched non-fluorinated, partially fluorinated, or fully fluorinated alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 14 carbon atoms; c is 0 or 1.

[0174] In another preferred embodiment of the present invention, in the compounds of formula (I), formula (I#), formula (I'), formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h), formula (I'-i) and formula (I''), 11 , R5, R6 and R7 act as monomers for the preparation of an ophthalmic device or a precursor article for producing an ophthalmic device as described above, or for the preparation of an oligomer, polymer or copolymer according to the invention or within a compound according to the invention, and have the following preferred meanings: Preferably, R6 and R7 are H. Preferably, c is 1.

[0175] Preferably, R5 is H, methyl, ethyl, or phenyl. Particularly preferably, R5 is H or methyl.

[0176] Preferably, X 11 is C(=O), OC(=O) or C(=O)O. Particularly preferably, X 11 is C(=O)O.

[0177] Therefore, a preferred alkenyl group of formula (4) as the polymerizable group R1 according to the present invention is represented by any one selected from the group consisting of formula (4-1), formula (4-2), formula (4-3), formula (4-4), formula (4-5), formula (4-6), formula (4-7), formula (4-8), formula (4-9), formula (4-10), formula (4-11) and formula (4-12).

[0178] [ka]

[0179] The alkenyl group of formula (4) particularly preferred as the polymerizable group R1 according to the present invention is represented by any one selected from the group consisting of the above-mentioned formulas (4-1), (4-2), (4-3), (4-5), (4-6), (4-11) and (4-12).

[0180] The alkenyl group represented by formula (4-1) is called a methacrylate, and the alkenyl group represented by formula (4-2) is called an acrylate.

[0181] The preferred group R1 is preferably combined with the preferred group of the linking element -R2- and / or the linking element Y-R2-. As known to those skilled in the art of organic chemistry, combinations in which two O atoms or one O atom and one S atom are directly bonded to each other are excluded.

[0182] Therefore, the substituents Y-R2-R1 in the formulae (I), (I#), (I'), (I'-a), (I'-b), (I'-c), (I'-d), (I'-e), (I'-f), (I'-g), (I'-h), (I'-i) and (I'') are particularly preferably O-(CH2)5-R 1、O-(CH2)6-R 1 、O-(CH2)7-R 1 、O-(CH2)8-R 1 、O-(CH2)9-R 1 、O-(CH2) 10 -R 1 、O-(CH2) 11 -R 1 、O-(CH2) 12 -R 1 、O-(CH2) 13 -R 1 、O-(CH2)2-S-(CH2)2-R 1 、O-(CH2)2-SO2-(CH2)2-R 1 、O-(CH2)2-S-(CH2)2-S-(CH2)2-R 1 、O-(CH2)2-O-(CH2)2-O-(CH2)2-R 1 、O-(CH2)2-S-(CH2)2-O-(CH2)2-R 1 、O-(CH2)2-SO2-(CH2)2-O-(CH2)2-R 1 、O-(CH2)2-SO2-(CH2)2-S-(CH2)2-R 1 、O-(CH2)2-O-(CH2)2-O-(CH2)2-O-(CH2)2-R 1 、O-(CH2)2-O-(CH2)2-S-(CH2)2-O-(CH2)2-R 1 、O-(CH2)2-S-(CH2)2-O-(CH2)2-S-(CH2)2-R 1 、O-(CH2)2-SO2-(CH2)2-O-(CH2)2-SO2-(CH2)2-R 1 、O-(CH2)2-S-(CH2)2-S-(CH2)2-S-(CH2)2-R 1 、O-(CH2)2-SO2-(CH2)2-S-(CH2)2-SO2-(CH2)2-R 1 、O-(CH2)2-SO2-(CH2)2-SO2-(CH2)2-SO2-(CH2)2-R 1 、O-(CH2)2-O-(CH2)2-SO2-(CH2)2-O-(CH2)2-R 1 、O-(CH2)3-(CF2)-(CH2)3-R 1, O-(CH2)-(CF2)3-(CH2)-R 1 , O-(CH2)2-(CF2)4-(CH2)2-R 1 , O-(CH2)-[CH(CF3)]-(CH2)-R 1 , O-(CH2)-[C(CH3)CF3]-(CH2)-R 1 ,O-(CH2)-[CH(CH2CF3)]-(CH2)-R 1 , O-(CH2)-[C(CH3)(CH2CF3)]-(CH2)-R 1 , O-(CH2)2-(CF2)-O-(CF2)-O-(CF2)-(CH2)2-R 1 and O-(CH2)-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)-R 1 (Wherein R1 is selected from the group consisting of alkenyl of formula (4-1), formula (4-2), formula (4-3), formula (4-4), formula (4-5), formula (4-6), formula (4-7), formula (4-8), formula (4-9), formula (4-10), formula (4-11), or formula (4-12); -(CH2)5-R 1 , -(CH2)6-R 1 , -(CH2)7-R 1 , -(CH2)8-R 1 , -(CH2)9-R 1 , -(CH2) 10 -R 1 , -(CH2) 11 -R 1 , -(CH2) 12 -R 1 , -(CH2) 13 -R 1 , -(CH2)2-S-(CH2)2-R 1 , -(CH2)2-SO2-(CH2)2-R 1 , -(CH2)2-S-(CH2)2-S-(CH2)2-R 1 , -(CH2)2-O-(CH2)2-O-(CH2)2-R 1 , -(CH2)2-S-(CH2)2-O-(CH2)2-R 1 , -(CH2)2-SO2-(CH2)2-O-(CH2)2-R 1 , -(CH2)2-SO2-(CH2)2-S-(CH2)2-R1 , -(CH2)2-O-(CH2)2-O-(CH2)2-O-(CH2)2-R 1 , -(CH2)2-O-(CH2)2-S-(CH2)2-O-(CH2)2-R 1 , -(CH2)2-S-(CH2)2-O-(CH2)2-S-(CH2)2-R 1 , -(CH2)2-SO2-(CH2)2-O-(CH2)2-SO2-(CH2)2-R 1 , -(CH2)2-S-(CH2)2-S-(CH2)2-S-(CH2)2-R 1 , -(CH2)2-SO2-(CH2)2-S-(CH2)2-SO2-(CH2)2-R 1 , -(CH2)2-SO2-(CH2)2-SO2-(CH2)2-SO2-(CH2)2-R 1 , -(CH2)2-O-(CH2)2-SO2-(CH2)2-O-(CH2)2-R 1 , -(CH2)3-(CF2)-(CH2)3-R 1 , -(CH2)-(CF2)3-(CH2)-R 1 , -(CH2)2-(CF2)4-(CH2)2-R 1 , -(CH2)-[CH(CF3)]-(CH2)-R 1 , -(CH2)-[C(CH3)CF3]-(CH2)-R 1 , -(CH2)-[CH(CH2CF3)]-(CH2)-R 1 , -(CH2)-[C(CH3)(CH2CF3)]-(CH2)-R 1 , -(CH2)2-(CF2)-O-(CF2)-O-(CF2)-(CH2)2-R 1 and -(CH2)-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)-R 1 (Wherein, Y is a bond, and R1 is selected from the group consisting of alkenyl of formula (4-1), formula (4-2), formula (4-3), formula (4-4), formula (4-5), formula (4-6), formula (4-7), formula (4-8), formula (4-9), formula (4-10), formula (4-11), or formula (4-12); S-(CH2)5-R 1 , S-(CH2)6-R 1、S-(CH2)7-R 1 、S-(CH2)8-R 1 、S-(CH2)9-R 1 、S-(CH2) 10 -R 1 、S-(CH2) 11 -R 1 、S-(CH2) 12 -R 1 、S-(CH2) 13 -R 1 、S-(CH2)2-S-(CH2)2-R 1 、S-(CH2)2-SO2-(CH2)2-R 1 、S-(CH2)2-S-(CH2)2-S-(CH2)2-R 1 、S-(CH2)2-O-(CH2)2-O-(CH2)2-R 1 、S-(CH2)2-S-(CH2)2-O-(CH2)2-R 1 、S-(CH2)2-SO2-(CH2)2-O-(CH2)2-R 1 、S-(CH2)2-SO2-(CH2)2-S-(CH2)2-R 1 、S-(CH2)2-O-(CH2)2-O-(CH2)2-O-(CH2)2-R 1 、S-(CH2)2-O-(CH2)2-S-(CH2)2-O-(CH2)2-R 1 、S-(CH2)2-S-(CH2)2-O-(CH2)2-S-(CH2)2-R 1 、S-(CH2)2-SO2-(CH2)2-O-(CH2)2-SO2-(CH2)2-R 1 、S-(CH2)2-S-(CH2)2-S-(CH2)2-S-(CH2)2-R 1 、S-(CH2)2-SO2-(CH2)2-S-(CH2)2-SO2-(CH2)2-R 1 、S-(CH2)2-SO2-(CH2)2-SO2-(CH2)2-SO2-(CH2)2-R 1 、S-(CH2)2-O-(CH2)2-SO2-(CH2)2-O-(CH2)2-R 1 、S-(CH2)3-(CF2)-(CH2)3-R 1 、S-(CH2)-(CF2)3-(CH2)-R 1, S-(CH2)2-(CF2)4-(CH2)2-R 1 , S-(CH2)-[CH(CF3)]-(CH2)-R 1 , S-(CH2)-[C(CH3)CF3]-(CH2)-R 1 , S-(CH2)-[CH(CH2CF3)]-(CH2)-R 1 , S-(CH2)-[C(CH3)(CH2CF3)]-(CH2)-R 1 , S-(CH2)2-(CF2)-O-(CF2)-O-(CF2)-(CH2)2-R 1 and S-(CH2)-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)-R 1 (Wherein R1 is selected from the group consisting of alkenyl of formula (4-1), formula (4-2), formula (4-3), formula (4-4), formula (4-5), formula (4-6), formula (4-7), formula (4-8), formula (4-9), formula (4-10), formula (4-11), or formula (4-12); SO2-(CH2)5-R 1 , SO2-(CH2)6-R 1 , SO2-(CH2)7-R 1 , SO2-(CH2)8-R 1 , SO2-(CH2)9-R 1 , SO2-(CH2) 10 -R 1 , SO2-(CH2) 11 -R 1 , SO2-(CH2) 12 -R 1 , SO2-(CH2) 13 -R 1 , SO2-(CH2)2-S-(CH2)2-R 1 , SO2-(CH2)2-SO2-(CH2)2-R 1 ,SO2-(CH2)2-S-(CH2)2-S-(CH2)2-R 1 ,SO2-(CH2)2-O-(CH2)2-O-(CH2)2-R 1 ,SO2-(CH2)2-S-(CH2)2-O-(CH2)2-R 1 , SO2-(CH2)2-SO2-(CH2)2-O-(CH2)2-R 1, SO2-(CH2)2-SO2-(CH2)2-S-(CH2)2-R 1 , SO2-(CH2)2-O-(CH2)2-O-(CH2)2-O-(CH2)2-R 1 , SO2-(CH2)2-O-(CH2)2-S-(CH2)2-O-(CH2)2-R 1 , SO2-(CH2)2-S-(CH2)2-O-(CH2)2-S-(CH2)2-R 1 , SO2-(CH2)2-SO2-(CH2)2-O-(CH2)2-SO2-(CH2)2-R 1 , SO2-(CH2)2-S-(CH2)2-S-(CH2)2-S-(CH2)2-R 1 , SO2-(CH2)2-SO2-(CH2)2-S-(CH2)2-SO2-(CH2)2-R 1 , SO2-(CH2)2-SO2-(CH2)2-SO2-(CH2)2-SO2-(CH2)2-R 1 , SO2-(CH2)2-O-(CH2)2-SO2-(CH2)2-O-(CH2)2-R 1 , SO2-(CH2)3-(CF2)-(CH2)3-R 1 , SO2-(CH2)-(CF2)3-(CH2)-R 1 , SO2-(CH2)2-(CF2)4-(CH2)2-R 1 , SO2-(CH2)-[CH(CF3)]-(CH2)-R 1 , SO2-(CH2)-[C(CH3)CF3]-(CH2)-R 1 , SO2-(CH2)-[CH(CH2CF3)]-(CH2)-R 1 , SO2-(CH2)-[C(CH3)(CH2CF3)]-(CH2)-R 1 , SO2-(CH2)2-(CF2)-O-(CF2)-O-(CF2)-(CH2)2-R 1 and SO2-(CH2)-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)-R 1(wherein R1 is selected from the group consisting of alkenyl of formula (4-1), formula (4-2), formula (4-3), formula (4-4), formula (4-5), formula (4-6), formula (4-7), formula (4-8), formula (4-9), formula (4-10), formula (4-11), or formula (4-12).

[0183] Therefore, the substituents N-R2-R1 in the formulae (I), (I#), (I'), (I'-a), (I'-b), (I'-c), (I'-d), (I'-e), (I'-f), (I'-g), (I'-h), (I'-i) and (I'') are particularly preferably N-(CH2)5-R 1 , N-(CH2)6-R 1 , N-(CH2)7-R 1 , N-(CH2)8-R 1 , N-(CH2)9-R 1 , N-(CH2) 10 -R 1 , N-(CH2) 11 -R 1 , N-(CH2) 12 -R 1 , N-(CH2) 13 -R 1 , N-(CH2)2-S-(CH2)2-R 1 , N-(CH2)2-SO2-(CH2)2-R 1 , N-(CH2)2-S-(CH2)2-S-(CH2)2-R 1 , N-(CH2)2-O-(CH2)2-O-(CH2)2-R 1 , N-(CH2)2-S-(CH2)2-O-(CH2)2-R 1 , N-(CH2)2-SO2-(CH2)2-O-(CH2)2-R 1 , N-(CH2)2-SO2-(CH2)2-S-(CH2)2-R 1 , N-(CH2)2-O-(CH2)2-O-(CH2)2-O-(CH2)2-R 1 , N-(CH2)2-O-(CH2)2-S-(CH2)2-O-(CH2)2-R 1 , N-(CH2)2-S-(CH2)2-O-(CH2)2-S-(CH2)2-R 1, N-(CH2)2-SO2-(CH2)2-O-(CH2)2-SO2-(CH2)2-R 1 , N-(CH2)2-S-(CH2)2-S-(CH2)2-S-(CH2)2-R 1 , N-(CH2)2-SO2-(CH2)2-S-(CH2)2-SO2-(CH2)2-R 1 , N-(CH2)2-SO2-(CH2)2-SO2-(CH2)2-SO2-(CH2)2-R 1 , N-(CH2)2-O-(CH2)2-SO2-(CH2)2-O-(CH2)2-R 1 , N-(CH2)3-(CF2)-(CH2)3-R 1 , N-(CH2)-(CF2)3-(CH2)-R 1 , N-(CH2)2-(CF2)4-(CH2)2-R 1 , N-(CH2)-[CH(CF3)]-(CH2)-R 1 , N-(CH2)-[C(CH3)CF3]-(CH2)-R 1 , N-(CH2)-[CH(CH2CF3)]-(CH2)-R 1 , N-(CH2)-[C(CH3)(CH2CF3)]-(CH2)-R 1 , N-(CH2)2-(CF2)-O-(CF2)-O-(CF2)-(CH2)2-R 1 and N-(CH2)-(CF2)-O-(CF2)-O-(CF2)-O-(CF2)-(CH2)-R 1 (wherein R1 is selected from the group consisting of alkenyl of formula (4-1), formula (4-2), formula (4-3), formula (4-4), formula (4-5), formula (4-6), formula (4-7), formula (4-8), formula (4-9), formula (4-10), formula (4-11), or formula (4-12).

[0184] Particularly preferably, the compounds of formula (I), formula (I#), formula (I'), formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h), formula (I'-i), and formula (I'') contain a polymerizable group R1 and are represented by formula (4-1), formula (4-2), formula (4-5), formula (4-6), formula (4-11), and formula (4-12).

[0185] Very particularly preferably, the compounds of formula (I), formula (I#), formula (I'), formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h), formula (I'-i) and formula (I'') comprise a polymerizable group R1 which is a methacryl or acryl group represented by formula (4-1) and formula (4-2).

[0186] Accordingly, the present invention further relates to an ophthalmic device or a precursor article for producing an ophthalmic device comprising a polymerized compound of Formula (I), Formula (I#), Formula (I'), Formula (I'-a), Formula (I'-b), Formula (I'-c), Formula (I'-d), Formula (I'-e), Formula (I'-f), Formula (I'-g), Formula (I'-h), Formula (I'-i) and / or Formula (I''), as described above, or preferably as described above, wherein R1 in each occurrence is independently an acrylic group or a methacrylic group.

[0187] Thus, the present invention further relates to compounds of formula (I), formula (I#), formula (I'), formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h), formula (I'-i) and / or formula (I''), as described above, or preferably as described above, wherein R1 in each occurrence is independently an acrylic group or a methacrylic group.

[0188] Examples of compounds / monomers of formula I), (I#), (I'), (I'-a), (I'-b), (I'-c), (I'-d), (I'-e), (I'-f), (I'-g), (I'-h), (I'-i) and / or (I'') are the following compounds (A-001) to (A-162), as shown in Table 1.

[0189] Table 1-1

[0190] Table 1-2

[0191] Table 1-3

[0192] Table 1-4

[0193] Table 1-5

[0194] Table 1-6

[0195] Table 1-7

[0196] Table 1-8

[0197] Table 1-9

[0198] Table 1-10

[0199] [Table 1-11]

[0200] [Table 1-12]

[0201] [Table 1-13]

[0202] [Table 1-14]

[0203] [Table 1-15]

[0204] [Table 1-16]

[0205] The compounds of the present application can be synthesized by methods known to those skilled in the art. However, for certain intermediate materials of the present application, novel preparation methods are described herein. Preferably, all syntheses are carried out under an inert atmosphere using dry solvents.

[0206] An exemplary reaction sequence is shown in Scheme 1 for a compound of formula (I#) where X is O, Y is O, m is 1, A is N, A, A, and A are CR″, all further symbols and subscripts have the meanings previously described, and the polymerizable group R is as shown in Scheme 1.

[0207] [ka]

[0208] The first type of reaction is the formation of cinnamic acid derivatives.

[0209] The second type of reaction is the oxidative formation of pyridine 1-oxide.

[0210] The third type of reaction is the base-induced ring closure reaction.

[0211] The fourth type of reaction is the methoxy deprotection reaction.

[0212] The fifth type of reaction is the Williamson ether synthesis reaction.

[0213] The sixth type of reaction is the esterification reaction.

[0214] A representative synthesis of compound A-001 is shown in Scheme 1-1. Part of the synthetic sequence is adopted to the desired chemical structure of A-001 by the method previously described by D. Wang et al., Org. Lett. 2017, 19, 984-987.

[0215] [ka]

[0216] An alternative reaction sequence for compounds of formula (I#) where X is O, Y is O, m is 0, A is N, and A and A are CR″ is shown in Scheme 2-1, where all further symbols and subscripts have the previously defined meanings and the polymerizable group R is as shown in Scheme 2-1.

[0217] [ka]

[0218] The first step of the synthesis described in Scheme 2-1 is not known in the art and is therefore another embodiment of the present invention.

[0219] The second type of reaction is a methoxy deprotection reaction.

[0220] The third type of reaction is the Williamson ether synthesis reaction.

[0221] The fourth type of reaction is the esterification reaction.

[0222] An alternative reaction sequence for compounds of formula (I#) where X is O, Y is O, m is 1, A is N, and A, A, and A are CR″ is further shown in Scheme 2-2, where all additional symbols and subscripts have the previously defined meanings and the polymerizable group R is as shown in Scheme 2-2.

[0223] [ka]

[0224] Again, the first type of reaction is a reaction according to the process of the present invention, which is described in more detail below.

[0225] The second type of reaction is a methoxy deprotection reaction.

[0226] The third type of reaction is the Williamson ether synthesis reaction.

[0227] The fourth type of reaction is the esterification reaction.

[0228] An alternative reaction sequence for compounds of formula (I#) where X is O, Y is O, m is 0, A is N, and A and A are CR″ is further shown in Scheme 2-3, where all additional symbols and subscripts have the previously mentioned meanings.

[0229] [ka]

[0230] The first type of reaction is according to the process of the present invention, which is further described below.

[0231] The second type of reaction is a methoxy deprotection reaction.

[0232] The third type of reaction is the Williamson ether synthesis reaction.

[0233] The fourth type of reaction is the hydrosilylation reaction.

[0234] Accordingly, the present invention further provides a compound of formula (syn-Ia), (syn-Ib), (syn-Ic), (syn-Id), (syn-Ie), (syn-If), (syn-Ig), (syn-Ih), (syn-Ii), (syn-Ij), (syn-Ik), (syn-IL), (syn-Im), (syn-In), (syn-Io), (syn-Ip), (syn-Iq), (syn-Ir) or (syn-Is),

[0235] [ka]

[0236] [ka]

[0237] [ka]

[0238] [ka] (Wherein A1, A2, A3 and A4 are each independently CR″; R3 is H; m1, Y, R2, R4 and

[0239] [ka] and R″ has the meanings as defined above or preferably as defined above), The preparation process includes (syn-1-a), (syn-1-b), (syn-1-c), (syn-1-d), (syn-1-e), (syn-1-f), (syn-1-g), (syn-1-h), (syn-1-i), ( syn-1-j), (syn-1-k), (syn-1-L), (syn-1-m), (syn-1-n), (syn-1-o), (syn-1-p), (syn-1-q), (syn-1-r) or (syn-1-s),

[0240] [ka] Compounds of wherein A1, A2, A3 and A4 are each independently CR″, R3 is H, and R″ is defined as above or preferably as above; Formula (syn-2)

[0241] [ka] in the presence of a buffer system. (Wherein m1, Y, R2, R4 and

[0242] [ka] teeth, as defined above or preferably has the meaning as defined above).

[0243] Suitable buffer systems are lithium methoxide with acetic anhydride, potassium carbonate with acetic anhydride, cesium carbonate with acetic anhydride, potassium tert-butoxide with acetic anhydride, triethylamine with acetic anhydride, pyridine with acetic anhydride, potassium acetate with acetic anhydride.

[0244] A preferred buffer system is potassium acetate with acetic anhydride.

[0245] The compounds of formula (syn-1-a), (syn-1-b), (syn-1-c), (syn-1-d), (syn-1-e), (syn-1-f), (syn-1-g), (syn-1-h), (syn-1-i), (syn-1-j), (syn-1-k), (syn-1-L), (syn-1-m), (syn-1-n), (syn-1-o), (syn-1-p), (syn-1-q), (syn-1-r), (syn-1-s) and (syn-2) are commercially available or can be obtained by known synthetic processes.

[0246] The reaction can be carried out both in open and also in closed equipment.

[0247] It is preferred to mix the starting materials in an inert gas atmosphere whose oxygen content is at most 1000 ppm, particularly preferably less than 500 ppm, and even more preferably at most 100 ppm.

[0248] Therefore, the present invention further relates to a process as described above, wherein the compounds of formula (syn-1-a) to formula (syn-1-s) and formula (syn-2) are used in equimolar amounts.

[0249] Thus, the present invention further relates to a process as described above, wherein part of the buffer system, i.e., potassium acetate, is used in an amount of 0.17 to 1.45 equivalents relative to the starting material. The process preferably uses 0.38 to 1.25 equivalents of potassium acetate. The process more preferably uses 0.45 to 1.00 equivalents of potassium acetate.

[0250] Therefore, the present invention further relates to a process as described above in which acetic anhydride is used as part of a buffer system in an amount of 5.0 to 50.0 equivalents relative to the starting material. The process preferably uses an amount of 10.0 to 25.0 equivalents of acetic anhydride. The process more preferably uses an amount of 12.5 to 20.0 equivalents of acetic anhydride.

[0251] It is further preferred that in the process according to the invention, the reaction of the reactants is followed by a purification step to remove the final product of formula I above from by-products or reaction products.

[0252] Suitable purification steps include separation of readily volatile components by distillation or concentration, extraction with organic solvents, or a combination of these methods. Each known separation method can be used for this purpose or can be combined.

[0253] The present invention therefore further relates to a process as described above, characterized in that the reaction is followed by a purification step.

[0254] The reaction mixture obtained from the reaction is preferably cooled to room temperature and a protic solvent such as water is added. The resulting solid is preferably further recrystallized from an organic solvent.

[0255] Suitable solvents for recrystallization are alcohols such as methanol, ethanol, propanol, ethers such as tetrahydrofuran, diethyl ether, methyl t-butyl ether or dimethoxyethane, or acetone. Preferably, 2-propanol is used.

[0256] In one embodiment of the process according to the invention, as described above, the reaction takes place without organic solvents (solvent-free), i.e. simply in a buffer system as previously described.

[0257] In a preferred embodiment of the process according to the invention, as described above in the embodiments thereof, or as preferred, the reaction of compounds (syn-1-a), (syn-1-b), (syn-1-c), (syn-1-d), (syn-1-e), (syn-1-f), (syn-1-g), (syn-1-h), (syn-1-i), (syn-1-j), (syn-1-k), (syn-1-L), (syn-1-m), (syn-1-n), (syn-1-o), (syn-1-p), (syn-1-q), (syn-1-r) or (syn-1-s) and (syn-2) is carried out at a reaction temperature of 50° C. to 160° C. The reaction is preferably carried out at a temperature of 60° C. to 140° C.

[0258] Further exemplary processes according to the present invention are described in Schemes 2 to 4 below, in which the starting material of formula (syn-1-a) can be replaced with any of the materials of formula (syn-1-c) to formula (syn-1-s) accordingly.

[0259] [ka]

[0260] An advantage of the preparation process according to the invention is that the reaction does not require additional organic solvents and that the solubility of the materials of formula (syn-Ia), (syn-Ib), (syn-Ic), (syn-Id), (syn-Ie), (syn-If), (syn-Ig), (syn-Ih), (syn-Ii), (syn-Ij), (syn-Ik), (syn-IL), (syn-Im), (syn-In), (syn-Io), (syn-Ip), (syn-Iq), (syn-Ir) and (syn-Is) is high in organic solvents, preferably the aforementioned organic solvents. The intermediate materials of formula (syn-Ia), (syn-Ib), (syn-Ic), (syn-Id), (syn-Ie), (syn-If), (syn-Ig), (syn-Ih), (syn-Ii), (syn-Ij), (syn-Ik), (syn-IL), (syn-Im), (syn-In), (syn-Io), (syn-Ip), (syn-Iq), (syn-Ir) and (syn-Is) can be more easily isolated from the reaction mixture.

[0261] The present invention further relates to a process for the synthesis of a compound of formula (I), (I') or (I''), wherein X is O, Y is O and the further symbols and indices have the meanings described above or below, wherein in step 1 a material of formula (syn-Ia), (syn-Ib), (syn-Ic), (syn-Id), (syn-Ie), (syn-If), (syn-Ig), (syn-Ih), (syn-Ii), (syn-Ij), (syn-Ik), (syn-IL), (syn-Im), (syn-In), (syn-Io), (syn-Ip), (syn-Iq), (syn-Ir) or (syn-Is) is prepared,

[0262] [ka]

[0263] [ka]

[0264] [ka]

[0265] [ka] In the formula, A1, A2, A3, and A4 are each independently CR″; R3 is H; m1, Y, R2, R4, and

[0266] [ka] and R″ has the meanings given above or preferably given above, Such preparations include (syn-1-a), (syn-1-b), (syn-1-c), (syn-1-d), (syn-1-e), (syn-1-f), (syn-1-g), (syn-1-h), (syn-1-i), syn-1-j), (syn-1-k), (syn-1-L), (syn-1-m), (syn-1-n), (syn-1-o), (syn-1-p), (syn-1-q), (syn-1-r) or (syn-1-s),

[0267] [ka] and a compound of wherein A1, A2, A3 and A4 are each independently CR″, R3 is H, and R′ is defined as above or preferably as above; Compound of formula (syn-2)

[0268] [ka] (Wherein m1, Y, R2, R4 and

[0269] [ka] teeth, as defined above or preferably having the meanings as defined above) in the presence of a buffer system as defined above or preferably as defined above, followed by a deprotection reaction, a Williamson ether synthesis reaction or a thioether synthesis reaction, and optionally an esterification reaction or a silylation reaction.

[0270] A representative synthesis of compound A-097 is described in Schemes 2-5. As previously mentioned, the first step of the described synthesis is an example of a process according to the present invention.

[0271] [ka]

[0272] The first type of reaction is the process of the present invention as described above.

[0273] The second type of reaction is a methoxy deprotection reaction.

[0274] The third type of reaction is the Williamson ether synthesis reaction.

[0275] The fourth type of reaction is the esterification reaction.

[0276] As mentioned above, the compounds / monomers of formula (I), (I#), (I'), (I'-a), (I'-b), (I'-c), (I'-d), (I'-e), (I'-f), (I'-g), (I'-h), (I'-i) and (I'') as described above or preferably as described above contain polymerizable groups and are pre-treated as monomers for oligomerization or polymerization.

[0277] Thus, the present invention further relates to an oligomer, polymer or copolymer comprising at least one polymeric compound of formula (I), formula (I#), formula (I'), formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h), formula (I'-i) or formula (I'') as described above, or preferably as described above.

[0278] The term "polymer" generally refers to a molecule of high relative molecular weight, the structure of which essentially comprises a plurality of repeating units derived, actually or conceptually, from molecules of lower relative molecular weight (PAC, 1996, 68, 2291). The term "polymer" includes homopolymers and copolymers, unless otherwise specified in this specification. The term "oligomer" generally refers to a molecule of relatively medium molecular weight, the structure of which essentially comprises a plurality of small units derived, actually or conceptually, from molecules of lower relative molecular weight (PAC, 1996, 68, 2291). In the preferred sense according to the present invention, polymer refers to a compound having 30 or more repeating units, and oligomer refers to a compound containing more than 1 and less than 30 repeating units.

[0279] In the above and below, in a polymer, oligomer, a formula representing a compound of formula (I), formula (I#), formula (I'), formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h), formula (I'-i) or formula (I''), or a monomer unit or polymer formed from a compound of formula (I), formula (I#), formula (I'), formula (I'), formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h), formula (I'-i) or formula (I''), an asterisk (" * ") indicates a bond to an adjacent repeating unit in a polymer or oligomer chain or to a terminal group.

[0280] Suitable terminating groups are known to those skilled in the art and will vary depending on the polymerization method used.

[0281] The terms "repeating unit" and "monomer unit" refer to a constitutional repeating unit (CRU), which is the smallest building block, the repetition of which constitutes a regular polymer, a regular oligomeric molecule, a regular block, or a regular chain (PAC, 1996, 68, 2291).

[0282] Unless otherwise stated, molecular weights are number average molecular weights M determined by gel permeation chromatography (GPC) against polystyrene standards in eluents such as tetrahydrofuran, trichloromethane (TCM, chloroform), chlorobenzene, or 1,2,4-trichlorobenzene. n or weight average molecular weight M W Unless otherwise stated, tetrahydrofuran is used as the solvent. The degree of polymerization (n) is given by n = M n / M U where M U is the molecular weight of a single repeat unit as described in J.M.G. Cowie, Polymers: Chemistry & Physics of Modern Materials, Blackie, Glasgow, 1991.

[0283] In polymers, including copolymers, according to the present invention, the total number of repeat units n is preferably ≧30, very preferably ≧100, most preferably ≧200, preferably up to 5000, very preferably up to 3000, most preferably up to 2000, including any combination of the aforementioned lower and upper limits of n.

[0284] The polymers of the present invention include homopolymers, statistical copolymers, random copolymers, alternating copolymers and block copolymers, as well as combinations of the foregoing.

[0285] Throughout the description and claims of this specification, the terms "comprise" and "contain" and variations thereof, such as "comprising" and "comprises," mean "including but not limited to" and are not intended to (and do not) exclude other elements.

[0286] Preferably, the polymerizable group R1 forms a regioregular, alternating, regiorandom, statistical, block or random homopolymer or copolymer backbone or is part of a polymer backbone, R1 having the meanings described or preferably previously described.

[0287] Preferably, such oligomers, polymers or copolymers according to the invention comprise building blocks M according to formula (I), formula (I') or formula (I'') 0 Including,

[0288] [ka] wherein, in each occurrence, the polymerizable group R1 is polymerized to form a regioregular, alternating, regiorandom, statistical, block or random oligomeric or polymeric backbone or is part of a copolymeric backbone, and all symbols and subscripts used within formula (I), formula (I') and formula (I'') have or preferably have the meanings previously described.

[0289] The present invention further relates to a structural unit M according to formula (I), formula (I′) or formula (I″) as described above, or preferably according to formula (I), formula (I′) or formula (I″) as described above. 0 wherein R1, in each occurrence, is polymerized to form a regioregular, alternating, regiorandom, statistical, block, or random oligomeric or polymeric backbone, or is part of a copolymeric backbone.

[0290] Preferably, such polymerizable group R1 is of formula (1-p), formula (2-p), formula (3-p) or formula (4-p):

[0291] [ka] The asterisks " in formulas (1-p) to (4-p) * " represents a bond to an adjacent repeating unit or terminal group in a polymer chain or oligomer chain, and the asterisk " ** " represents a bond to the remainder of formula (I) as described above or preferably as described above, and R5, R6, R7, X 11 and c have the meanings given above or preferably given above.

[0292] The present invention further relates to an ophthalmic device or a precursor article for producing an ophthalmic device as described above or preferably below, wherein the polymerizable group R1 is of formula (1-p), (2-p), (3-p) or (4-p) as described above.

[0293] The present invention further relates to an oligomer, polymer or copolymer as described above or preferably below, wherein the polymerizable group R1 is of the above formula (1-p), formula (2-p), formula (3-p) or formula (4-p).

[0294] Particularly preferably, such oligomers, polymers or copolymers according to the invention have the formula (M 0 -I'-a), formula (M 0 -I'-b), formula (M 0 -I'-c), formula (M 0 -I'-d), formula (M 0 -I'-e), formula (M 0 -I'-f), formula (M 0 -I'-g), formula (M 0 -I'-h), formula (M 0 -I'-i) or formula (M 0 -I'') structural unit M 0 Including,

[0295] [ka]

[0296] [ka]

[0297] [ka] In the formula, R1, -R2-, X, Y0, Y, A1, A2, A3, A4, R3, R4, R5, R6, R7, X 11 , c and

[0298] [ka] has the meaning as defined above or preferably as defined above or below for the compounds of formula (I), formula (I#), formula (I'), formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h), formula (I'-i) or formula (I'').

[0299] As known to those skilled in the art of organic chemistry, combinations in which two O atoms or one O atom and one S atom are directly bonded to each other are excluded.

[0300] The present invention further relates to an ophthalmic device or a precursor article for producing an ophthalmic device as described above or preferably below, comprising a building block M 0 is calculated by the formula (M 0 -I'-a), formula (M 0 -I'-b), formula (M 0 -I'-c), formula (M 0 -I'-d), formula (M 0 -I'-e), formula (M 0 -I'-f), formula (M 0 -I'-g), formula (M 0 -I'-h), formula (M 0 -I'-i) or formula (M0 -I'') and the asterisk " * ", in each occurrence, indicates a bond to an adjacent repeat unit in a polymer or oligomer chain or to a terminal group.

[0301] Preferably, such oligomers, polymers or copolymers according to the invention comprise building blocks (M 0 -I'-a), (M 0 -I'-b), (M 0 -I'-c), (M 0 -I'-d), (M 0 -I'-e), (M 0 -I'-f), (M 0 -I'-g), (M 0 -I'-h), (M 0 -I'-i) or (M 0 -I″), wherein -R2 is -(CH2)5-, -(CH2)6-, -(CH2)7-, -(CH2)8-, -(CH2)9-, -(CH2) 10 -, -(CH2) 11 -, -(CH2) 12 -, -(CH2) 13-, -(CH2)2-S-(CH2)2-, -(CH2)2-SO2-(CH2)2-, -(CH2)2-S-(CH2)2-S-(CH2)2-, -(CH2)2-O-(CH2)2-O-(CH2)2-, - (CH2)2-S-(CH2)2-O-(CH2)2-, -(CH2)2-SO2-(CH2)2-O-(CH2)2-, -(CH2)2-SO2-(CH2)2-S-(CH2)2-, -(CH2)2-O-(C H2)2-O-(CH2)2-O-(CH2)2-, -(CH2)2-O-(CH2)2-S-(CH2)2-O-(CH2)2-, -(CH2)2-S-(CH2)2-O-(CH2)2-S-(CH2)2-, -(CH2)2-SO2-(CH2)2-O-(CH2)2-SO2-(CH2)2-, -(CH2)2-S-(CH2)2-S-(CH2)2-S-(CH2)2-, -(CH2)2-SO2-(CH2)2-S -(CH2)2-SO2-(CH2)2-, -(CH2)2-SO2-(CH2)2-SO2-(CH2)2-SO2-(CH2)2-, -(CH2)2-O-(CH2)2-SO2-(CH2)2-O-(CH2 )2-, -(CH2)3-(CF2)-(CH2)3-, -(CH2)-(CF2)3-(CH2)-, -(CH2)2-(CF2)4-(CH2)2-, -(CH2)-[CH(CF3)]-(CH2)-, -( is selected from: —CH)—[C(CH)CF]—(CH)—, —(CH)—[CH(CHCF)]—(CH)—, —(CH)—[C(CH)(CHCF)]—(CH)—, —(CH)—(CF)—O—(CF)—O—(CF)—(CH)— and —(CH)—(CF)—O—(CF)—O—(CF)—O—(CF)—(CH)—, or preferably have the meanings as previously mentioned, Y is O, S, SO or a bond or preferably has the meanings described above, R3 is H, F, a linear alkyl group having 1 to 4 carbon atoms or a linear alkoxy group having 1 to 4 carbon atoms, or preferably has the meanings given above, X 11is selected from the group consisting of O, S, O-SO2, SO2-O, C(=O), OC(=O), C(=O)O, S(C=O) and (C=O)S, or preferably has the meaning described above; R6 and R7 are H; R5 is H, methyl, ethyl or phenyl or preferably has the meanings given above, c is 1, X, Y0, Y, A1, A2, A3, A4 and

[0302] [ka] has the meaning as defined above or preferably as defined above or below for the compounds of formula (I), formula (I#), formula (I'), formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h), formula (I'-i) or formula (I'').

[0303] Preferably, such oligomers, polymers or copolymers are included in ophthalmic devices or precursor articles for making ophthalmic devices according to the present invention.

[0304] Particularly preferably, such oligomers, polymers or copolymers according to the invention comprise the aforementioned structural units (M 0 -I'-a), (M 0 -I'-b), (M 0 -I'-c), (M 0 -I'-d), (M 0 -I'-e), (M 0 -I'-f), (M 0 -I'-g), (M 0 -I'-h), (M 0 -I'-i) or (M 0 -I″), wherein -R2- is -(CH2)5-, -(CH2)6-, -(CH2)7-, -(CH2)8-, -(CH2)9-, -(CH2) 10 -, -(CH2) 11 -, -(CH2) 12-, -(CH2) 13 -, -(CH2)2-S-(CH2)2-, -(CH2)2-SO2-(CH2)2-, -(CH2)2-S-(CH2)2-S-(CH2)2-, -(CH2)2-O -(CH2)2-O-(CH2)2-, -(CH2)2-O-(CH2)2-O-(CH2)2-O-(CH2)2-, -(CH2)2-O-(CH2)2-S-(CH 2) selected from -O-(CH)-, -(CH)-S-(CH)-O-(CH)-S-(CH)-, -(CH)-S-(CH)-S-(CH)-S-(CH)-, -(CH)-SO-(CH)-S-(CH)-SO-(CH)- or preferably have the meanings as previously mentioned, Y is O, S, SO or a bond or preferably has the meanings described above, R3 is H, F, a linear alkyl group having 1 to 4 carbon atoms or a linear alkoxy group having 1 to 4 carbon atoms, or preferably has the meanings given above, X 11 is selected from the group consisting of O, S, O-SO2, SO2-O, C(=O), OC(=O), C(=O)O, S(C=O) and (C=O)S, or preferably has the meaning described above; R6 and R7 are H; R5 is H, methyl, ethyl or phenyl or preferably has the meanings given above, c is 1,

[0305] [ka] is at the 3-position of the photoactive chromophore as described above or is of formula (I#), X, Y0, Y, A1, A2, A3, A4 and

[0306] [ka] has the meaning as defined above or preferably as defined above or below for the compounds of formula (I), formula (I#), formula (I'), formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h), formula (I'-i) or formula (I'').

[0307] Particularly preferably, such oligomers, polymers or copolymers are included in ophthalmic devices or precursor articles for producing ophthalmic devices according to the present invention.

[0308] The copolymer may comprise one or more polymerized compounds of formula (I), (I#), (I'), (I'-a), (I'-b), (I'-c), (I'-d), (I'-e), (I'-f), (I'-g), (I'-h), (I'-i) or (I'') as described above or preferably as described above, or a copolymer of formula (M 0 -I'-a), formula (M 0 -I'-b), formula (M 0 -I'-c), formula (M 0 -I'-d), formula (M 0 -I'-e), formula (M 0 -I'-f), formula (M 0 -I'-g), formula (M 0 -I'-h), formula (M 0 -I'-i) and / or formula (M 0 -I″) 0 or one or more constitutional units (M 0 -001)~(M 0 -162), which may be the same or different from each other, and may be an oligomer or polymer comprising one or more structural units M 2 may be the same or different from each other. 2 is in units of M 0 Preferably, the one or more structural units M 2Styrene, ethoxyethyl methacrylate (EOEMA), methyl methacrylate (MMA), methyl acrylate, n-alkyl acrylate (n-alkyl group containing 2 to 20 carbon atoms), n-alkyl methacrylate (n-alkyl group containing 2 to 20 carbon atoms), i-alkyl acrylate (i-alkyl group containing 3 to 20 carbon atoms), i-alkyl methacrylate (i-alkyl group containing 3 to 20 carbon atoms), ethoxyethoxyethyl acrylate (EEEA), 2-hydroxyethyl methacrylate (HEMA), tetrahydrofuryl methacrylate (THFMA), glycidyl methacrylate (GMA), 16-hydroxyhexadecyl acrylate, 16-hydroxyhexadecyl methacrylate, 18-hydroxyoctadecyl acrylate, 18-hydroxyoctadecyl methacrylate, 2-phenoxyethyl acrylate acrylate (EGPEA), heptafluorobutyl acrylate, heptafluorobutyl methacrylate, hexafluorobutyl acrylate, hexafluorobutyl methacrylate, hexafluoroisopropyl acrylate, hexafluoroisopropyl methacrylate, octafluoropentyl acrylate, octafluoropentyl methacrylate, pentafluoropropyl acrylate, pentafluoropropyl methacrylate, tetrafluoropropyl methacrylate, trifluoroethyl acrylate, trifluoroethyl methacrylate, bisphenol A diacrylate-1EO / phenol (BPADA), 2-[3'-2'H-benzotriazol-2'-yl)-4'-hydroxyphenyl]ethyl methacrylate (BTPEM), or ethylene glycol dimethacrylate.

[0309] The present invention therefore further relates to an ophthalmic device as described, or preferably as described above, or a precursor article for producing an ophthalmic device, comprising at least one polymeric compound of formula (I), formula (I′) or formula (I″), or a polymeric compound of formula (M 0 -I'-a), formula (M 0 -I'-b), formula (M 0 -I'-c), formula (M0 -I'-d), formula (M 0 -I'-e), formula (M 0 -I'-f), formula (M 0 -I'-g), formula (M 0 -I'-h), formula (M 0 -I'-i) and / or formula (M 0 -I'') structural unit M 0 or one or more constitutional units (M 0 -001)~(M 0-162), including styrene, ethoxyethyl methacrylate (EOEMA), methyl methacrylate (MMA), methyl acrylate, n-alkyl acrylates (n-alkyl groups containing 2 to 20 carbon atoms), n-alkyl methacrylates (n-alkyl groups containing 2 to 20 carbon atoms), i-alkyl acrylates (i-alkyl groups containing 3 to 20 carbon atoms), i-alkyl methacrylates (i-alkyl groups containing 3 to 20 carbon atoms), ethoxyethoxyethyl acrylate (EEEA), 2-hydroxyethyl methacrylate (HEMA), tetrahydrofuryl methacrylate (THFMA), glycidyl methacrylate (GMA), 16-hydroxyhexadecyl acrylate, 16-hydroxyhexadecyl methacrylate, 18-hydroxyoctadecyl acrylate, 18-hydroxyoctadecyl methacrylate, 2-phenoxyethyl acrylate (EGPEA), heptafluorobutyl acrylate, heptafluorobutyl methacrylate, hexafluorobutyl acrylate, hexafluorobutyl methacrylate, hexafluoroisopropyl acrylate, hexafluoroisopropyl methacrylate, octafluoropentyl acrylate, octafluoropentyl methacrylate, pentafluoropropyl acrylate, pentafluoropropyl methacrylate, tetrafluoropropyl methacrylate, trifluoroethyl acrylate, trifluoroethyl methacrylate, bisphenol A diacrylate-1 EO / phenol (BPADA), 2-[3'-2'H-benzotriazol-2'-yl)-4'-hydroxyphenyl]ethyl methacrylate (BTPEM), or ethylene glycol dimethacrylate.

[0310] Particularly preferably, the at least one further polymerized monomer is selected from methyl methacrylate, 2-hydroxyethyl methacrylate, 2-phenoxyethyl acrylate, ethoxyethoxyethyl acrylate, 8-methylnonyl methacrylate, n-butyl methacrylate, 2-ethylhexyl methacrylate, or mixtures thereof.

[0311] Particularly preferably, such copolymers are included in ophthalmic devices or precursor articles for producing ophthalmic devices according to the present invention.

[0312] Alternatively, the oligomer or polymer, preferably polymer, according to the present invention is a homopolymer, i.e. an oligomer or polymer, preferably a polymer, and has the above or preferably the above formula (M 0 -I'-a), formula (M 0 -I'-b), formula (M 0 -I'-c), formula (M 0 -I'-d), formula (M 0 -I'-e), formula (M 0 -I'-f), formula (M 0 -I'-g), formula (M 0 -I'-h), formula (M 0 -I'-i) or formula (M 0 -I″) 0 , or as described below (M 0 -001)~(M 0 -162), including all structural units M 0 are the same.

[0313] Exemplary homopolymer compounds based on the compounds of Formula (I), Formula (I#), Formula (I'), Formula (I'-a), Formula (I'-b), Formula (I'-c), Formula (I'-d), Formula (I'-e), Formula (I'-f), Formula (I'-g), Formula (I'-h), Formula (I'-i) and / or Formula (I'') are the following compounds (P-001) to (P-162), as shown in Table 2.

[0314] [Table 2-1]

[0315] [Table 2-2]

[0316] [Table 2-3]

[0317] Table 2-4

[0318] Table 2-5

[0319] Table 2-6

[0320] Table 2-7

[0321] Table 2-8

[0322] Table 2-9

[0323] Table 2-10

[0324] Table 2-11

[0325] Table 2-12

[0326] Table 2-13

[0327] [Table 2-14]

[0328] [Table 2-15]

[0329] [Table 2-16]

[0330] [Table 2-17]

[0331] The letter n gives the degree of polymerization as explained above.

[0332] Exemplary building blocks M based on compounds of formula (I), formula (I#), formula (I'), formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h), formula (I'-i) and / or formula (I'') 0 , or the formula (M 0 -I'-a), formula (M 0 -I'-b), formula (M 0 -I'-c), formula (M 0 -I'-d), formula (M 0 -I'-e), formula (M 0 -I'-f), formula (M 0 -I'-g), formula (M 0 -I'-h), formula (M 0 -I'-i) or formula (M 0 -I'') structural unit M 0 The following compounds (M 0 -001)~(M 0 -162).

[0333] Table 3-1

[0334] Table 3-2

[0335] Table 3-3

[0336] Table 3-4

[0337] Table 3-5

[0338] Table 3-6

[0339] Table 3-7

[0340] Table 3-8

[0341] Table 3-9

[0342] Table 3-10

[0343] Table 3-11

[0344] [Table 3-12]

[0345] [Table 3-13]

[0346] [Table 3-14]

[0347] [Table 3-15]

[0348] [Table 3-16]

[0349] [Table 3-17]

[0350] Preferably, the copolymer according to the invention as described above or preferably as described above comprises one or more of the aforementioned structural units M having the aforementioned or preferably as described above substituents. 0 in a molar ratio m1, and one or more structural units M 2 in a molar ratio m2, wherein the ratio m1:m2 is at least 0.01 and at most 100.

[0351] Particularly preferably, such copolymers are included in ophthalmic devices or precursor articles for producing ophthalmic devices according to the present invention.

[0352] The oligomers, polymers or copolymers, preferably polymers or copolymers according to the present invention as mentioned above or preferably described, may be crosslinked. Particularly preferably, such polymers or copolymers are included in an ophthalmic device or a precursor article for producing an ophthalmic device according to the present invention.

[0353] The oligomers or polymers of the present invention can be prepared by any suitable method. However, it is preferred that the oligomers, polymers, and copolymers of the present invention are prepared by radical polymerization, and the polymerization reaction is initiated by a suitable radical polymerization initiator. For purposes of the present invention, the type of radical polymerization initiator is not particularly limited and can be any suitable radical-generating compound. Such compounds are well known to those skilled in the art. Suitable polymerization initiators can be selected from thermal initiators or photoinitiators, i.e., compounds that generate radicals upon exposure to heat or irradiation with light of a suitable wavelength. Examples of suitable thermal polymerization initiators can be selected from the group of compounds containing one or more peroxide groups, i.e., the group -OO-, and / or one or more azo groups, i.e., compounds containing the group -N≡N-.

[0354] Suitable polymerization initiators containing one or more peroxide groups may be selected, for example, from the group consisting of t-butyl(peroxy-2-ethyl-hexanoate), di-(tert-butylcyclohexyl)peroxydicarbonate, and benzoyl peroxide.

[0355] Suitable polymerization initiators containing one or more azo groups may be selected, for example, from the group consisting of 1,1'-azobis(cyclohexanecarbonitrile) and 2,2'azobis(cyclohexanecarbonitrile) (AIBN).

[0356] Suitable examples of photoinitiators are dimethylaminobenzoate / camphorquinone, diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO) or phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide (BAPO).

[0357] When a photoinitiator is used as the polymerization initiator, the wavelength required to decompose the photoinitiator is preferably different from the wavelength required to irradiate the compounds of the present application to change their optical properties.

[0358] Preferably, the radical initiator is used in an amount of at least 0.0001 equivalent and at most 0.1 equivalent of the main monomer. Such a radical initiator can be a thermal initiator, for example, azobisisobutyronitrile (AIBN) or a photochemical initiator such as dimethylaminobenzoate / camphorquinone, diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO) or phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide (BAPO).

[0359] The present invention also relates to a polymerization composition.

[0360] Depending on the intended use of the composition as described, or preferably as described above, further different components may be included, such as for example selected from the group consisting of UV absorbers, antioxidants and crosslinkers.

[0361] The cross-linking agent may also be referred to as a cross-linking agent.

[0362] The present invention also relates to at least one compound of formula (I), formula (I#), formula (I'), formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h), formula (I'-i) or formula (I'') or compounds (A-001) to (A-162) as described or preferably as described above, and / or an oligomer having at least one reactive group remaining for polymerization as described above or preferably as described above. and a copolymer and / or a polymer, and / or a crosslinking agent, and / or an ultraviolet absorber, and / or a radical initiator, and optionally a further monomer different from the compounds of formula (I), (I#), (I'), (I'-a), (I'-b), (I'-c), (I'-d), (I'-e), (I'-f), (I'-g), (I'-h), (I'-i), or (I''), or compounds (A-001) to (A-162).

[0363] The compositions comprising at least one compound of the formula (I), (I#), (I'), (I'-a), (I'-b), (I'-c), (I'-d), (I'-e), (I'-f), (I'-g), (I'-h), (I'-i) or (I'') described or preferably described above, or compounds (A-001) to (A-162), or the oligomer or polymer according to the present invention described above, are primarily used for the synthesis of block copolymers, provided that the oligomer or polymer has at least one reactive group capable of reacting with a monomer.

[0364] The compositions may include, comprise, consist essentially of, or consist of essential or optional ingredients. All compounds or components that can be used in the compositions are either known and commercially available, or can be synthesized by known processes or as described herein.

[0365] The components of the composition according to the invention are combined in amounts such that the resulting oligomer, polymer or copolymer according to the invention contains at least 2% to 100% by weight, preferably 3% to 70% by weight, particularly preferably 4% to 51% by weight, and very particularly preferably 5% to 45% by weight of polymerized photoactive chromophores of formula (I), (I#), (I'), (I'-a), (I'-b), (I'-c), (I'-d), (I'-e), (I'-f), (I'-g), (I'-h), (I'-i) or (I'').

[0366] The components of the composition according to the invention are combined in amounts such that the resulting oligomer, polymer or copolymer constituting the material of an ophthalmic device or a precursor article for producing an ophthalmic device according to the invention contains at least 2% to 100% by weight, preferably 3% to 70% by weight, particularly preferably 4% to 51% by weight, and very particularly preferably 5% to 45% by weight of polymerized photoactive chromophores of formula (I), (I#), (I'), (I'-a), (I'-b), (I'-c), (I'-d), (I'-e), (I'-f), (I'-g), (I'-h), (I'-i) or (I'').

[0367] The ultraviolet absorber that can be used in the present composition is not particularly limited, and can be easily selected from those generally known to those skilled in the art.Generally, suitable ultraviolet absorber is unsaturated compound, preferably compound that comprises one or more selected from the group consisting of olefin group, aryl group and heteroaryl group, and these groups can be present in any combination.

[0368] Suitable UV absorbers for use in the present compositions can be selected from those containing a group selected from benzotriazoles, benzophenones, and triazines. Suitable UV absorbers are described, for example, in U.S. Patent Nos. 5,290,892, 5,331,073, and 5,693,095.

[0369] Suitable UV absorbers include 2-(3-(t-butyl)-4-hydroxy-5-(5-methoxy-2-benzotriazolyl)phenoxy)ethyl methacrylate, 3-(3-(t-butyl)-4-hydroxy-5-(5-methoxy-2-benzotriazolyl)phenoxy)propyl methacrylate, 3-(3-t-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl)propyl methacrylate, 3-(3-(tert-butyl)-4-hydroxy-5-(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)phenoxy)propyl methacrylate, 2-(2-hydroxy-5-vinylphenyl)-2H-benzotriazole, allyl-2-hydroxybenzophenone, 2-allyl-6-(2H-benzotriazol-2-yl)-p-cresol, 4-methacryloxy-2-hydroxybenzophenone, 2-methyl-4-hydroxybenzophenone, 2-methyl-6-(2H-benzotriazol-2-yl)-p-cresol, 4-methyl-2 ... -(2'-Hydroxy-3'-methallyl-5'-methylphenyl)benzotriazole, 2-hydroxy-4-methacryloyloxybenzophenone, 4-acryloylethoxy-2-hydroxybenzophenone, 2-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl]ethyl methacrylate, 2-(2'-hydroxy-5'-methacrylamidophenyl)-5-methoxybenzotriazole, 2-(2'-hydroxy-5'-methacrylamidophenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-5'-methacryloxypropylphenyl)benzotriazole, 2-(2'-hydroxy-5'-methacryloylpropyl-3'-tert-butyl-phenyl)-5-methoxy-2H-benzotriazole, 2-(3-(tert-butyl)-4-hydroxy-5-(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)phenoxy)ethyl methacrylate, 2-[3'-tert-butyl-2'-hydroxy-5'-(3''-methacryloyloxypropyl)phenyl]-5-chlorobenzotriazole, 2-{2'-hydroxy-3'-tert-butyl-5'-[3'-methacryloylpropoxy]phenyl}-5-methoxy-2H-benzotriazole, 2-[3'tert-butyl-5'-(3''-dimethylvinylsilylpropoxy)-2'-hydroxyphenyl [4-benzoyl-3-hydroxyphenoxy]ethyl acrylate, or a combination thereof.

[0370] Preferred UV absorbers are selected from the group consisting of 2-[3'-2'H-benzotriazol-2'-yl)-4'-hydroxyphenyl]ethyl methacrylate (BTPEM), 2-(3-(t-butyl)-4-hydroxy-5-(5-methoxy-2-benzotriazolyl)phenoxy)ethyl methacrylate, 3-(3-(t-butyl)-4-hydroxy-5-(5-methoxy-2-benzotriazolyl)phenoxy)propyl methacrylate, 3-(3-t-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl)propyl methacrylate, which can be polymerized with the monomers described above or preferably those described above.

[0371] A suitable crosslinking agent may be used to impart elastomeric properties to the compositions of the present invention and the ophthalmic devices or precursor articles produced therefrom. Typically, any suitable di- or trifunctional monomer can be used as the crosslinking agent. Such monomers are generally well known to those skilled in the art and include poly(ethylene glycol) diacrylate, poly(ethylene glycol) dimethacrylate, ethylene glycol dimethacrylate (EGDMA), ethylene glycol diacrylate, 1,3-propanediol diacrylate, 1,6-hexanediol diacrylate, 1,8-octanediol diacrylate, 1,11-undecanediol diacrylate, 1,12-dodecyl diacrylate, 1,15-pentadecanediol diacrylate, It may be selected from the group consisting of 1,16-hexadecanediol diacrylate, 1,18-octadecanediol diacrylate, 1,3-propanediol dimethacrylate, 1,6-hexanediol dimethacrylate, 1,8-octanediol dimethacrylate, 1,11-undecanediol dimethacrylate, 1,12-dodecyl dimethacrylate, 1,15-pentadecanediol dimethacrylate, 1,16-hexadecanediol dimethacrylate, and 1,18-octadecanediol dimethacrylate.

[0372] Preferred cross-linking agents may be selected from the following group of compounds:

[0373] [ka]

[0374] Ethylene glycol dimethacrylate (EGDMA) is particularly preferred.

[0375] Suitable antioxidants are phenyl acrylate derivatives with a hindered phenol moiety. Preferred antioxidants are:

[0376] [ka]

[0377] The compounds of formula (I), formula (I#), formula (I'), formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h), formula (I'-i) or formula (I'') according to the present invention, or compounds (A-001) to (A-162), as described or preferably as described above, 0 -I'-a), formula (M 0 -I'-b), formula (M 0 -I'-c), formula (M 0 -I'-d), formula (M 0 -I'-e), formula (M 0 -I'-f), formula (M 0 -I'-g), formula (M 0 -I'-h), formula (M 0 -I'-i) or formula (M 0 -I″) 0 or one or more structural units (M 0 -001)~(M 0 -162), those oligomers, polymers, or copolymers described or preferably described above are particularly well suited for use in optically active devices, such as the ophthalmic devices described above.

[0378] The compounds of formula (I), formula (I#), formula (I'), formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h), formula (I'-i) or formula (I'') according to the present invention, or compounds (A-001) to (A-162), as described or preferably as described above, 0 -I'-a), formula (M 0 -I'-b), formula (M 0 -I'-c), formula (M 0 -I'-d), formula (M 0 -I'-e), formula (M 0 -I'-f), formula (M 0 -I'-g), formula (M 0 -I'-h), formula (M0 -I'-i) or formula (M 0 -I″) 0 or one or more structural units (M 0 -001)~(M 0 The oligomers, polymers, or copolymers thereof described above, including (but not limited to) any of the above-described compounds, are susceptible to two-photon or multi-photon absorption. Accordingly, the ophthalmic devices and precursor articles for manufacturing the ophthalmic devices are susceptible to two-photon or multi-photon absorption.

[0379] The ophthalmic device according to the invention, preferably a system for two-photon or multi-photon irradiation of an intraocular lens preferably placed in a patient's eye, is not limited. Some examples are described below.

[0380] Therefore, the present invention also relates to a precursor article for manufacturing an ophthalmic device, said precursor article being a polymer having a structure as described above or preferably having the formula (M 0 -I'-a), formula (M 0 -I'-b), formula (M 0 -I'-c), formula (M 0 -I'-d), formula (M 0 -I'-e), formula (M 0 -I'-f), formula (M 0 -I'-g), formula (M 0 -I'-h), formula (M 0 -I'-i) or formula (M 0 -I″) 0 , or one or more structural units (M 0 -001)~(M 0 -162), or preferably a blank that can be converted into an optically active ophthalmic device comprising at least one oligomer, polymer or copolymer as described above.

[0381] A preferred ophthalmic device is an optically active ophthalmic device. Examples of such ophthalmic devices or ocular implants include lenses, keratoprostheses, and corneal inlays or rings. More preferably, the ophthalmic device or ocular implant is a lens article. Most preferably, the ophthalmic device is a lens. The type of lens is not limited and may include a contact lens or an intraocular lens. Most preferably, the ophthalmic device is an intraocular lens, which may be, for example, a posterior chamber intraocular lens or an anterior chamber intraocular lens.

[0382] The blanks of the present invention may be produced as a step in a manufacturing process used to make ophthalmic devices, preferably intraocular lenses, as described above. For example, but not by way of limitation, the manufacturing process may include the steps of polymer synthesis, polymer sheet casting, blank cutting, optical lathe cutting, optical milling, haptic grinding or mounting, polishing, solvent extraction, sterilization, and packaging, while the term polymer is used as described above or preferably as described above.

[0383] The ophthalmic device or precursor article for producing an ophthalmic device according to the invention as described above, or preferably as described above, comprises: at least one compound of formula (I), formula (I#), formula (I'), formula (I'-a), formula (I'-b), formula (I'-c), formula (I'-d), formula (I'-e), formula (I'-f), formula (I'-g), formula (I'-h), formula (I'-i) or formula (I'') as described herein or preferably as described herein, or compounds (A-001) to (A-162), and / or as described herein or preferably as described herein, but with at least one reactive group remaining for polymerization, and optionally providing a composition comprising an oligomer or polymer having the formula (I), (I#), (I'), (I'-a), (I'-b), (I'-c), (I'-d), (I'-e), (I'-f), (I'-g), (I'-h), (I'-i) or (I'') as described herein or preferably as described herein, or a further monomer different from the compounds of compounds (A-001) to (A-162), and / or a crosslinker, and / or an ultraviolet absorber, and / or a radical initiator; - then forming an ophthalmic device or precursor article from the composition; The compound is formed by a process including:

[0384] Intraocular lenses according to the present invention are believed to exhibit particularly advantageous properties in that they are sufficiently flexible to be rolled or folded, such that a much smaller incision is required for their insertion into the eye, which is believed to allow for improved healing of the eye, particularly with respect to the time it takes for the eye to heal.

[0385] The type of intraocular lens is not limited in any way. It can be, for example, a pseudophakic intraocular lens or a phakic intraocular lens. The former type replaces the eye's natural crystalline lens, usually to replace a removed cataract lens. The latter type is used to supplement the existing lens and function as a permanent corrective lens implanted in the anterior or posterior chamber of the eye to correct the eye's refractive error. It can include, for example, one or more optical components and one or more haptic components, where the one or more optical components function as lenses and the one or more haptic components are attached to the one or more optical components and hold the one or more optical components in place within the eye. The intraocular lens can be a one-piece or multi-piece design, depending on whether the one or more optical components and the one or more haptic components are formed from a single piece of material (one-piece design) or are fabricated separately and then assembled (multi-piece design). The intraocular lenses of the present invention are also designed, for example, to allow them to be rolled or folded small enough to fit through an incision in the eye, the incision being as small as possible, for example, up to 3 mm in length.

[0386] Furthermore, the intraocular lens according to the present invention allows for non-invasive adjustment of the optical properties, in particular the polarizability or refractive power, after implantation of the lens in the eye, thus reducing the need for post-operative visual aids or reducing or completely avoiding follow-up surgery.

[0387] To modify the optical properties, in particular the polarizability or refractive power, of an ophthalmic device according to the present invention, such as an intraocular lens, the device is exposed to radiation having a wavelength of at least 200 nm and up to 1500 nm, which radiation can be based on single-photon, two-photon or multi-photon processes, without limitation.

[0388] The present invention therefore also relates to a process for modifying the optical properties of an ophthalmic device as defined or preferably as defined herein or a precursor article for producing an ophthalmic device, said process comprising: - providing an ophthalmic device or a precursor article for manufacturing an ophthalmic device as defined herein; - subsequently exposing the ophthalmic device or the precursor article to radiation having a wavelength of at least 200 nm and at most 1500 nm.

[0389] Preferably, the radiation has a wavelength of at least 250 nm or 300 nm, more preferably at least 350 nm, even more preferably at least 400 nm, even more preferably at least 450 nm, and most preferably at least 500 nm. Preferably, the radiation has a wavelength of at most 1400 nm or 1300 nm or 1200 nm or 1100 nm or 1000 nm, more preferably at most 950 nm or 900 nm, even more preferably at most 850 nm, even more preferably at most 800 nm, and most preferably at most 750 nm.

[0390] The present invention therefore also relates to an ophthalmic device or a precursor article for manufacturing an ophthalmic device as described above or preferably obtainable by said irradiation process as described above or below.

[0391] Alternatively, the change in refractive power can be described as a modification of the refractive index of the ophthalmic device, as described above, or preferably as described above. Alternatively, the change in refractive power can be described as a modification of the refractive index of the intraocular lens, as described above, or preferably as described above. Illumination within a focal volume results in a refractive optical structure characterized by a change in the refractive index of the bulk of the ophthalmic device, or alternatively, relative to a non-irradiated portion of the ophthalmic device. Illumination within a focal volume results in a refractive optical structure characterized by a change in the refractive index of the bulk of the ophthalmic device or intraocular lens, or alternatively, relative to a non-irradiated portion of the ophthalmic device or intraocular lens. The change in polarizability or refractive index, in turn, can be used to form a patterned desired refractive structure within an optical ophthalmic device, as described above, or preferably as described above, or preferably within an intraocular lens, as described above, or preferably as described above.

[0392] Therefore, the present invention also relates to an ophthalmic device, as described above or preferably obtainable by the irradiation process described above or below, having a refractive optical structure characterized by a change in refractive index relative to the refractive index of the bulk of the ophthalmic device, or alternatively a change in refractive index relative to non-irradiated parts of the ophthalmic device.

[0393] It is preferred to provide a refractive structure that exhibits a change in refractive index and exhibits little or no scattering loss so that ablation or removal of the optical ophthalmic device, preferably an intraocular lens article, is not observed in the illuminated area.

[0394] In such a process, the illumination area of ​​the ophthalmic device as described above, or preferably as described above, can take the form of a two-dimensional or three-dimensional, area, or volume that fills a refractive structure that can provide spherical, aspherical, toroidal, or cylindrical correction. In fact, any optical structure can be formed to provide power correction in both physical directions. Furthermore, optical structures can be stacked vertically or written in separate planes within the ophthalmic device to act as a single lens element as described above, or preferably as described above.

[0395] Therefore, the present invention further relates to a method for locally adjusting the polarizability and / or refractive index of an ophthalmic device according to the present invention, preferably an intraocular lens placed in a patient's eye. The method particularly relates to the creation of an optical profile by adjusting the polarizability in a non-destructive manner by a two-photon or multi-photon process, which allows for different optical profiles compared to single-photon processes and may be advantageously used for the manufacture of ophthalmic devices according to the present invention comprising an optical profile.

[0396] Systems used in the two-photon or multi-photon processes advantageously enable postoperative and non-invasive adjustment of the optical properties / profile of implanted intraocular lenses (IOLs) to eliminate visual defects such as refractive errors. Furthermore, when manufacturing ophthalmic devices according to the present invention, the systems advantageously enable gentle preparation of the ophthalmic device, particularly to enable refractive structures that can provide spherical, aspherical, toroidal, or cylindrical correction and / or maintain the flexibility of the ophthalmic device once preparation of the ophthalmic device is complete. The polarizability of the ophthalmic device is modified based on a two-photon (or generally multi-photon) process, which allows for adjustment of the optical properties / profile of the ophthalmic device or allows for adjustment of the optical properties at different planes of the ophthalmic device. Furthermore, modification of the polarizability based on a two-photon or multi-photon process allows for improved maintenance of the flexibility of the ophthalmic device when treated with wavelengths between 400 nm and 590 nm.

[0397] The present invention therefore further relates to a process for adjusting the polarizability of an ophthalmic device according to the invention based on a two-photon or multi-photon absorption process, the process comprising: providing said ophthalmic device as described above or preferably as described above; adjusting the polarizability of the ophthalmic device through illumination of the ophthalmic device by using the system; Including, The system is an optical system and one or more two-photon or multi-photon illumination sources that illuminate the ophthalmic device with a focused illumination beam at a first wavelength and / or a second wavelength different from the first wavelength; a scanner coupled to one or more illumination sources and configured to scan the illumination beam across the ophthalmic device; an input unit coupled to one or more illumination sources and a scanner; an input unit configured to input data for processing the ophthalmic device by scanning the illumination beam across the ophthalmic device based on input data; The first wavelength is between 600 nm and 800 nm to locally decrease the polarizability of the ophthalmic device based on the treatment of the ophthalmic device, and the second wavelength is between 400 nm and 590 nm to locally increase the polarizability of the ophthalmic device based on the treatment of the ophthalmic device, thereby changing the polymeric optical material of the ophthalmic device, preferably with a significant difference in the UV / visible spectrum relative to the unirradiated polymeric optical material of the ophthalmic device.

[0398] Ultraviolet-visible spectroscopy or ultraviolet-visible spectrophotometry (UV-Vis or UV / Vis) is known to those skilled in the art. It refers to absorption or reflectance spectroscopy in the ultraviolet and part of the completely adjacent visible spectral region. Suitable UV / visible spectrometers are commercially available. The choice of UV / visible spectrometer is not critical for the comparison of the UV / visible spectrum of the initial ophthalmic device made in accordance with the present invention with the UV / visible spectrum of the irradiated ophthalmic device. As long as both measurements are made under comparable conditions, the results known to those skilled in the art can be compared. A suitable spectrometer is the UV / visible spectrometer Lambda 900 manufactured by Perkin Elmer.

[0399] This allows for particularly precise local variations in polarizability.

[0400] The present invention further relates to a method for correcting a patient's vision by modifying the refractive index of an intraocular lens in the patient's eye, comprising: Identifying and measuring the patient's degree of vision correction; determining the location and type of refractive structures to be written into the intraocular lens to correct the patient's vision; Thereafter, exposing the intraocular lens to two-photon or multi-photon radiation having a wavelength of 600 nm to 800 nm to locally reduce the polarizability of the intraocular lens or to expose the intraocular lens; or Thereafter, exposing the intraocular lens to two-photon or multi-photon radiation having a wavelength of 400 nm to 590 nm to locally increase the polarizability of the intraocular lens; Includes.

[0401] In the present application, input data is any kind of data used to create a treatment plan, which is defined as the translation of an ophthalmic need into control commands for the writing process of an ophthalmic device according to the present invention, during which an optical pattern is written by illumination within said ophthalmic device.

[0402] The term "control command" refers to a command that directly controls the writing process as defined above. A control command can, for example, control the movement of a scanner.

[0403] The term "scanner" used in the description is not part of the input unit according to the present invention. The "scanner" described herein is a component of the system that controls the movement of the illumination beam and is used in the process for adjusting the polarizability of the ophthalmic device according to the present invention.

[0404] Ophthalmic need refers to the desired optical profile that needs to be created in the ophthalmic device via the system as described.

[0405] The optical profile is the required change defined by the surgeon according to the patient's examination before or after the ophthalmic device, preferably an intraocular lens, is implanted, such as, but not limited to, a spherical full diopter change, a toric profile, an EDOF profile, or a bi-, tri-, or multifocal profile. Alternatively, the optical profile is the adjustment of the optical properties of the ophthalmic device.

[0406] The optical pattern is the desired change in polarizability that results in a change in refractive index in every voxel of the ophthalmic device.

[0407] The term "optics" as used herein as part of the system used in the process for adjusting the polarizability of an ophthalmic device according to the present invention includes all optical equipment necessary to control the spatial distribution of the illumination source (focal point) on the ophthalmic device. Important parameters of the focal point include the lateral focal point size (or beam waist) and focal length (or Rayleigh range). The optics includes all elements along the optical beam path that determine the focus, such as beam expanders, aperture stops, shutters, and focusing optics, especially microscope objectives or single aspheric lenses.

[0408] Multiphoton excitation occurs only near the focus, preferably by using ultrashort laser pulses, with the average power limited by the sample damage threshold, which is part of the input data defined previously.

[0409] Criteria for selection and optimization of system parameters: One ultimate goal is to provide localized refractive modification of the IOL after implantation as prescribed by the physician to improve the patient's vision. An important criterion for refractive modification procedures is the total treatment time required to achieve the desired results. It is generally recognized that such procedures should not exceed a few minutes to be considered feasible. State-of-the-art systems capable of localized refractive modification do not include approaches to achieve practical treatment times for IOL applications.

[0410] Consideration of system trade-offs and limitations: It is recognized that a practical, high-performance system capable of adjusting an ophthalmic device, generally or an IOL specifically, after implantation requires that its subcomponents, including the irradiation source, optics, scanner, and treatment plan, be treated as a system and therefore must be optimized together, with many interdependencies and tradeoffs between the subcomponents.

[0411] A key requirement for any system / parameter optimization is to stay within the safe limits of the ophthalmic device material, in the case of an IOL, and in the case of the eye with its components (e.g., the retina). Such requirements form the basis of the input data, as previously explained. In particular, two main damage mechanisms of radiation from the irradiation source, preferably a pulsed laser source, can be distinguished: single-pulse damage (dielectric breakdown and avalanche breakdown), and thermal damage, where the temperature of the lens material and / or eye heats up due to subsequent repeated pulses to the same volume. For example, the average power of a pulsed irradiation source is related to the heating and therefore potential damage of the lens material and / or eye. Therefore, while keeping the average power of the irradiation source below the overheating threshold of the lens material and / or eye, pulse energy and pulse repetition rate are inversely related to the product of pulse energy, where the number of pulses per second (= the inverse of the repetition rate) is equal to the average power.

[0412] Average power is defined as the pulse energy multiplied by the number of pulses per second and is characterized in watts (W).

[0413] Illuminance is equal to magnetic flux density (W / cm 2 ).

[0414] Radiation exposure is equal to the fluence (J / cm 2 ).

[0415] One overall goal is to minimize treatment time for IOL adjustment after implantation. While theoretically higher pulse energies with more frequent pulses (=higher repetition rates) can be applied, typically above 1 watt of average power, overheating creates unsafe conditions for the IOL material and the retina. Therefore, to stay within safe operating limits, while completing treatment of the full IOL volume in a few minutes, a preferred radiation exposure can be defined. The preferred radiation exposure is ≦5 kJ / cm2, particularly preferably <1 kJ / cm2, and very particularly preferably <0.3 kJ / cm2. This described radiation exposure also applies to the processes and methods according to the present invention, which are further described below.

[0416] In some cases, the treatment plan may be so excessive that it would exceed the laser safety limits for overheating. The treatment can be stopped to allow all of the ophthalmic device material and tissue affected by the treatment to cool. After cooling, the localization system compares the processed voxels in the ophthalmic device with the optical pattern, and treatment can continue.

[0417] As mentioned above, the process of adjusting the optical properties / profile of the ophthalmic device via the system and according to the requirements is performed according to the treatment plan mentioned above. According to the treatment plan, for example, a toric, spherical, multifocal or EDOF (extended depth of focus) profile can be written into the ophthalmic device according to the present invention. An algorithm can be used to write the profile, for example, a toric, spherical, multifocal or EDOF (extended depth of focus) profile.

[0418] By combining the desired optical profile information with the input data, the required optical pattern and control commands for the illumination source, optics, and scanner of the system as described above can be calculated. Further input data are lens data, such as the required laser energy for a particular refractive index change per voxel of the ophthalmic device material, and further patient data, such as the exact position and orientation of the ophthalmic device in the patient's eye, which is part of the treatment planning data.

[0419] The control commands can be updated and modified during the writing process by processing input data such as, for example, IR temperature measurements, in-process positioning data of the irradiation beam, refractive index data obtained from an ophthalmic device or the eye, e.g., acquired by OCT (Optical Coherence Tomography), and / or Scheimpflug images.

[0420] In further embodiments of the input data, the input data includes lens data of such ophthalmic device, preferably such intraocular lens, and / or treatment planning data related to a treatment plan for such treatment of such ophthalmic device. For example, the lens data may include data related to one or more of the polarizability and / or refractive index of the ophthalmic device as a function of the location, shape, diopter, cylinder, and sphere of each volume or portion of the ophthalmic device, and / or its individual deviations in said dimensions. Thus, the current polarizability may be increased or decreased at specific locations or volumes in one or more planes of the ophthalmic device depending on the current polarizability (or refractive index) and polarizability (or refractive index) obtained via treatment.

[0421] The treatment plan calculations may, in some examples, yield control commands that result in one or more treatment plans, which may include a scan strategy (scan strategy control command data (e.g., scan pattern and / or scan sequence and / or scan speed and / or scan duration and / or scan duration of the scan sequence and / or first and / or second wavelengths (e.g., nanosecond or picosecond or femtosecond pulses) and / or an illumination beam profile and / or radiation (photon) density and / or radiation of the illumination beam at the first and / or second wavelength) across the ophthalmic device. In-process input data such as the refractive index / polarizability of the ophthalmic device to be obtained based on the exposure, in particular the refractive index / polarizability to be obtained in association with a mapping of the refractive index / polarizability to be obtained for specific positions / coordinates of the ophthalmic device, rhexis dimension data of the rhexis dimensions, and eye data relating to the size and / or shape of the patient's eye, positioning data relating to the position and / or orientation of the ophthalmic device relative to the eye, and registration data relating to the identification of the patient and / or the patient's specific eye.

[0422] Preferably, the scan strategy control command data of the scan strategy is a scan pattern and / or a scan rate and / or pulse duration of pulses and / or radiation intensity, as further described below.

[0423] The parameters of the illumination beam(s) may then be adjusted in accordance with lens data and / or treatment planning data as defined herein to precisely (locally) change the polarization / refractive index of the ophthalmic device as desired.

[0424] Preferably, parameters of the radiation beam(s) are adjusted according to lens data and / or treatment planning data as described above or preferably as described herein.

[0425] Those skilled in the art are well aware that optimal illumination focus conditions are reached when the depth of field (Rayleigh range) of the illumination beam matches the desired thickness of the optical structure to be written into the ophthalmic device.

[0426] Those skilled in the art are well aware in this regard that optimal illumination focus conditions are reached when the depth of field (Rayleigh range) of the illumination beam is suitably matched to the local thickness of the ophthalmic device.

[0427] In a further embodiment, the lens data includes data regarding radiation absorption properties of the ophthalmic device (e.g., absorption and / or optical attenuation coefficients, which may be dependent on the wavelength of light), and the system is configured to tune the first wavelength and / or second wavelength of the ophthalmic device to locally change the polarizability based on a multi-photon absorption process. For example, based on the materials used in the ophthalmic device, a specific wavelength or wavelength range may be input for precise local change in the polarizability of the ophthalmic device.

[0428] The one or more irradiation sources as part of the system used in the process for adjusting the polarizability of an ophthalmic device according to the present invention may include one or more pulsed lasers that can be used to generate nanosecond pulses, preferably picosecond pulses, and more preferably femtosecond pulses. Preferably, one irradiation source is used. Particularly preferably, the one or more irradiation sources include one or more pulsed lasers that are used to generate femtosecond pulses. Particularly preferably, one pulsed laser is used to generate femtosecond pulses and is used as the irradiation for the system according to the present invention or the process and method according to the present invention.

[0429] In one embodiment, the one or more irradiation sources include lasers tunable to emit laser beams having first and second wavelengths, respectively, which may be particularly advantageous because a single laser may be used to (locally) increase or decrease the polarizability / refractive index of the ophthalmic device or intraocular lens, as desired.

[0430] In the process for adjusting the polarization rate of an ophthalmic device according to the present invention, different pulsed laser types are suitable for use as the irradiation source in the system. MHz lasers as well as kHz lasers are suitable and have their own advantages. For example, MHz laser systems operate at lower pulse energies, but the focused laser spot can be maintained on the μm scale (less than 1 μm to several μm), and therefore can be used for precise local index modification in all three dimensions to generate diffractive structures. A preferred MHz irradiation source is an 80 MHz laser with a pulse energy in the range of 0.1 to 10 nJ.

[0431] On the other hand, kHz lasers operate at higher pulse energies, typically 0.1-10 μJ, and therefore require larger spot sizes, e.g., 10-100 μm, to avoid damaging the lens material. However, a larger laser spot size implies a larger depth of field (=long Rayleigh range), which may equal or exceed the thickness of the ophthalmic device material. With such a long Rayleigh range, the refractive index layer by layer within the IOL may be modified, but not uniformly along a line around the focal point. Preferred kHz-irradiation sources are lasers with repetition rates of 100-500 kHz.

[0432] The average power of the irradiation source as described above or preferably as described above is preferably 300 to 600 mW, particularly preferably 400 to 500 mW.

[0433] The irradiation source as part of the system used in the process for adjusting the polarizability of an ophthalmic device according to the present invention preferably comprises a tunable laser capable of providing a variable wavelength in the range of about 680-1080 nm, such as a Ti:sapphire laser (e.g., Chameleon Ultra II by Coherent, Santa Clara, CA, USA). The system may also include an optical parametric oscillator (e.g., a frequency-doubled Chameleon Compact OPO-Vis by Coherent, Santa Clara, CA, USA).

[0434] The radiation source as part of the system used in the process for adjusting the polarizability of an ophthalmic device according to the present invention particularly preferably includes a femtosecond pump laser in conjunction with an optical parametric amplifier. The pump laser emits radiation at 1030 nm with an average power greater than 10 Watts in less than 350 fs pulses at a repetition rate of 0.1 to 700 kHz. The pump laser radiation is directed to an optical parametric amplifier, where the pump laser output is frequency-doubled and optically mixed to produce a final tunable output in the wavelength range of 600 nm to 800 nm. A preferred repetition rate is 50 to 600 kHz. A particularly preferred repetition rate is 100 to 500 kHz.

[0435] The radiation source as part of the system used in the process for adjusting the polarizability of an ophthalmic device according to the present invention preferably includes a femtosecond pump laser with an average power greater than 10 Watts at 1030 nm, in combination with an optical parametric amplifier emitting radiation pulses of less than 350 fs at a repetition rate of 1 to 700 kHz. The pump laser radiation is directed to an optical parametric amplifier with one or more second harmonic stages, resulting in a final optical output in the wavelength range of 400 nm to 590 nm. A preferred repetition rate is 50 to 600 kHz. A particularly preferred repetition rate is 100 to 500 kHz.

[0436] The laser types described above, or preferably the above, generate a collimated light beam with a diameter of a few millimeters, which is then directed to the optical system and scanner. The optical beam quality (characterized by the beam quality factor or beam propagation factor) is ideally 1.0-1.5, more ideally 1.0-1.3. According to DIN EN ISO 11146, the optical beam quality is given by the dimension M2.

[0437] The first wavelength of the illumination beam in the system used in the process of adjusting the polarizability of an ophthalmic device according to the present invention is between 600 nm and 800 nm, preferably between 650 nm and 750 nm, more preferably between 670 nm and 720 nm, more preferably between 680 and 710 nm, in order to (locally) reduce the polarizability (and therefore the refractive index) of the IOL.

[0438] The second wavelength of the illumination beam in the system used in the process of adjusting the polarizability of an ophthalmic device according to the present invention is between 400 nm and 590 nm, preferably between 500 nm and 580 nm, more preferably between 530 nm and 570 nm, in order to (locally) increase the polarizability (and therefore the refractive index) of the IOL.

[0439] This allows for particularly precise local variations in polarizability.

[0440] Optical elements in a system used in a process for adjusting the polarizability of an ophthalmic device according to the present invention: The primary function of the optical system is to focus the radiation beam, direct it from the radiation source, and direct it onto the ophthalmic device via a scanner. As mentioned above, the primary considerations are the spot size and depth of focus to minimize treatment time while remaining within the limits set by laser safety requirements and material damage, as described above as part of the general input data. The most important characteristics of the optical system are given by its numerical aperture (NA), along with its effective focal length (EFL) and the diameter of the radiation beam at the entrance aperture of the focusing optics. Furthermore, all optical elements in the system used in the process for adjusting the polarization index of an ophthalmic device according to the present invention should be selected for diffraction or nearly diffraction-limited properties so as not to substantially degrade the optical beam quality.

[0441] The spot size determines the spatial resolution that can be obtained, and different ophthalmic needs will require different spot sizes. Ideally, the spot size is between 1 and 100 μm, more ideally between 50 and 100 μm, to minimize processing time while reducing the possibility of material damage.

[0442] Scanner in a system used in the process for adjusting the polarizability of an ophthalmic device according to the present invention: The scanners used in the system used in the process for adjusting the polarizability of an ophthalmic device according to the present invention may include a galvanometer scanner, a piezoelectric scanner, a rotary scanner, or an acousto-optical modulator, or may be digital, such as a spatial light modulator, a digital micromirror device, or a stereolithography device. Preferably, the scanner as part of the system of the present invention according to the present invention is selected from a galvanometer scanner, a piezoelectric scanner, a rotary scanner, an acousto-optical modulator, a spatial light modulator, a digital micromirror device, or a stereolithography device. A preferred galvanometer scanner is a single pivot-point scanner.

[0443] Preferably, the scanner is configured to operate at a scanning speed of greater than 50 mm / sec, which allows treatment times to be kept short. As a general rule, treatment times should not exceed a few minutes per treatment session, preferably less than 10 minutes, more preferably less than 5 minutes, and most preferably less than 3 minutes.

[0444] The treatment area may be defined as the volume and size of the ophthalmic device, typically the optic of the ophthalmic device or intraocular lens, is 5mm to 7mm in diameter and typically 0.2mm to 2.0mm thick.

[0445] The optimal radiation exposure is less than 1 kJ / cm2, more ideally less than 0.3 kJ / cm2, to address the entire volume of the ophthalmic device while keeping the overall radiation exposure low and reducing treatment time.

[0446] Particularly preferably, a random scan pattern or interleaved scan lines are used to spread the illumination energy of the illumination beam.

[0447] Scanning can be performed in three modes: In bottom-up scanning, the laser can move from spot to spot with a specific dwell time on each spot ("bottom-up, spot-to-spot"); alternatively, in bottom-up scanning, the laser can dwell on overlapping spots ("bottom-up, spot overlay"); or alternatively, the laser can move at a fixed speed without dwelling on any spot ("moving at constant speed").

[0448] In one embodiment of the scan pattern, the IOL is scanned with the illumination source as described above, or preferably as described above, by thinning across the pupil. The IOL, contained in the capsular bag at the time of scanning, has previously been inserted through a corneal incision using conventional operating procedures. In this embodiment, the entire volume of the IOL is scanned, and the scanning is performed in a bottom-up manner (i.e., the portion of the IOL further from the cornea is scanned first), in which an optical profile is created to avoid unnecessary changes in the refractive index in the optical path.

[0449] As previously mentioned, a primary consideration in selecting a scanning program is minimizing localized heating of the ophthalmic device and / or the patient's eye, so various variables are used in the scanning program. Anatomical characteristics, such as Rhexis and pupil size, and optical characteristics, such as numerical aperture and laser pulse characteristics, are taken into account to create a laser program with a specific scanning speed and sequence. The relationship between the lens coordinate system and the eye coordinate system is automatically taken into account in this example.

[0450] The parameters of the scanning program and / or treatment plan are preferably the first and second wavelengths, scanning speed and sequence, positioning of the lens relative to the eye (e.g., in Cartesian coordinates), scanning strategy, resulting refractive index change (optical pattern), numerical aperture of the objective lens, Rhexis, optical diameter of the pupil and / or lens (in some instances about 6 mm), pulse duration of the laser beam (shape, intensity and xy positioning), laser safety when operating the laser, and centration relative to the lens and eye positioning.

[0451] In one embodiment of a system used in the process for adjusting the polarizability of an ophthalmic device according to the present invention, the photons generated by the laser are preferably directed through a mirror (e.g., as optical element 1) to, for example, a beam expander, which prepares the beam for a subsequent scanner and focusing optics. After passing through the beam expander, the photons are directed to a scanner (e.g., a galvanometer scanner, a piezoelectric scanner, a rotary scanner, an acousto-optical modulator, or digitally using a spatial light modulator, a digital micromirror device, or a stereolithography device).

[0452] After passing through the scanner, the laser beam travels through another optical system, such as a divider mirror. In this embodiment, the divider mirror splits the beam into a main imaging beam for ophthalmic device illumination and a beam for monitoring beam characteristics and positioning feedback. After the divider mirror, the optical beam is focused onto the ophthalmic device by an imaging group or focusing optics. In one embodiment, the imaging group includes a microscope objective or low NA optics to obtain a high numerical aperture (for μm-level spatial resolution) to enable higher pulse energies in the μJ range.

[0453] The system as described above may further include a microscope objective coupled to the scanner for focusing the illumination beam onto the ophthalmic device by the microscope objective, the microscope objective having a numerical aperture of 0.1 to 0.8, preferably 0.2 to 0.5, more preferably 0.2 to 0.4. Providing a microscope objective with such a numerical aperture may enable high illumination beam quality, particularly with regard to focusing and resolution characteristics of the beam used to process an intraocular lens.

[0454] The microscope objective comprises a typical lens configuration that allows for example correction of chromatic aberrations. The microscope objective is preferably coupled to an eye interface system, typically a suction system that holds the patient's eye in a fixed position, as further described below.

[0455] In a further embodiment of an objective for use in a system such as described above, the objective is an Olympus LUCPLFLN objective for focusing an illumination beam onto an ophthalmic device.

[0456] An alternative focusing optics / imaging group consists of a single aspheric lens, preferably with an effective focal length within 50-150 mm and a numerical aperture preferably between 0.025 and 0.1.

[0457] The above-described, or preferably the above-described, system may further comprise a positioning system for determining the position of the focal point of the irradiation beam within the eye of the patient, the positioning system being coupled to a scanner, and scanning of the irradiation beam across the intraocular lens by the scanner being based on the position of the focal point of the irradiation beam within the eye.

[0458] The positioning system may comprise a localization system such as an optical coherence tomography system, a confocal microscope, or a shear imperfect camera. The positioning system may be directly or indirectly coupled to a scanner. In some instances where a confocal microscope is used, the confocal microscope may be directly coupled to the scanner.

[0459] The positioning system described above is used to provide topographic data of the eye to the positioning system in order to determine the position of the laser focus relative to the eye and the intraocular lens in question.

[0460] Confocal microscopes use partially transparent mirrors to allow video imaging.

[0461] The system as described above, or preferably as described above, is preferably further configured to determine a position and / or orientation of the intraocular lens relative to the eye and the exit of the illumination beam, and wherein the scanning of the illumination beam across the intraocular lens by the scanner is based on the position and / or orientation of the intraocular lens relative to the eye. This may be particularly advantageous as the position of the intraocular lens may not be centered relative to the eye and the misalignment may be taken into account when treating the intraocular lens with the illumination beam(s).

[0462] With respect to the position of the IOL, at least two coordinate systems may be considered to be relevant, namely the coordinate system of the eye and the coordinate system of the lens in the eye, since both may not be centered relative to each other.

[0463] With respect to the position of the IOL, at least two coordinate systems may be considered relevant, namely the x, y, z coordinates of the eye and the x, y, z coordinates of the lens in the eye, since both may not be centered relative to each other.

[0464] In one embodiment, the localization system generates input data, including, for example, data regarding the lens position and / or orientation of the ophthalmic device within the eye, data relative to the laser beam exit, and / or optical power mapping of the eye and / or ophthalmic device, which are used to calculate the optical pattern or treatment duration.

[0465] Additionally, the localization system may generate input data during the writing process. These in-process input data may include, for example, data regarding the lens position and / or orientation of the ophthalmic device within the eye, and data relative to the laser beam exit, and / or optical power mapping of the eye and / or ophthalmic device. These data are used for in-process modification of the control commands used to generate the optical pattern.

[0466] The system as described above, or preferably as described above, may further comprise a temperature management unit coupled to one or both of (i) the one or more irradiation sources and (ii) the scanner, the temperature management unit configured to determine a temperature of a portion of the ophthalmic device during the treatment of the ophthalmic device by the scanning based on irradiation beam characteristics of the irradiation beam and ophthalmic device characteristics of the ophthalmic device, and the system configured to control one or both of (i) the one or more irradiation sources and (ii) the scanner based on the determination of the temperature, thereby ensuring that the eye and / or the ophthalmic device are not adversely affected by treatment with the irradiation beam.

[0467] Furthermore, the temperature management unit is preferably configured to predict the temperature of the ophthalmic device during said treatment, and said input data includes the predicted temperature, which may allow precautions to be taken to ensure that the eye and / or ophthalmic device are not potentially adversely affected upon treatment with the irradiation beam.

[0468] Alternatively, the thermal management unit is an infrared camera that logs the eye temperature and correlates the measured data with a common data set with calibration data to calculate the actual eye temperature.

[0469] In another embodiment, the temperature dependence of the refractive index is used for temperature control. In these examples, the system includes a power mapping device. Based on the deviation of the measured power map and the progression of the written predicted power map, the temperature within the lens can be calculated in the process.

[0470] In another embodiment, the temperature dependence of the emission spectrum is used for temperature control. In these examples, the system includes a UV-Vis spectrometer. Based on the deviation of the measured emission peak wavelength and / or peak width, the temperature of the focal point can be calculated in the process.

[0471] The system as described above, or preferably as described above, may further comprise an eye interface system configured to hold the eye of the patient in a fixed position. The eye interface system may comprise a suction system for fixing the position of the patient's eye during treatment.

[0472] The patient can be "docked" into the system in either a supine or standing position.

[0473] The system as described above, or preferably as described above, may further comprise a wireless or wired receiver and / or transceiver for one or more of: (i) sending control commands to one or more illumination sources; (ii) sending control commands to the scanner; and (iii) inputting control command data to the scanner required to create the light pattern.

[0474] Thus, one or more irradiation sources and / or scanners may be remotely controlled. Additionally or alternatively, data relating to one or both of the lens data and treatment planning data may be stored externally from the system and provided to the system as needed. In some examples, it may be preferable to provide a wired receiver or transceiver for controlling at least one or more irradiation sources and / or for controlling the scanner to reduce (or avoid) any delays in transmitting control signals to the one or more irradiation sources and / or scanner.

[0475] In another example, the receiver / transceiver transmits the treatment planning data and lens data to a central computing unit, which calculates the optical pattern and returns it as input data to the receiver, which provides it to the system.

[0476] The system as described above, or preferably as described above, may further comprise a device for locally measuring the refractive power of the ophthalmic device during said treatment of the ophthalmic device. Adjustments to one or more of the illumination source(s), scanner, and input data may be made during the treatment process.

[0477] The system as described above, or preferably as described above, may further comprise a refractometer for locally measuring the refractive index of the ophthalmic device during the treatment of the ophthalmic device. Adjustments to one or more of the illumination source(s), scanner, and input data may be made during the treatment process.

[0478] Further components of the system providing photons are optionally a cover in which all equipment is built, a power unit providing sufficient energy for the system and all subsystems and subsystems such as a suction system and / or a refrigerator.

[0479] In addition to the components mentioned above, a controller, firmware, and a graphics user interface (GUI) and treatment algorithms can be provided. To connect to the system, connectivity can be established via Bluetooth, Wi-Fi, or other ports such as RS-232.

[0480] The present invention further relates to a method for locally adjusting the polarizability of an intraocular lens according to the present invention placed in a patient's eye, the method comprising the steps of: scanning strategy control command data of a scanning strategy for said scanning of said irradiation beam across the intraocular lens (e.g. a scan pattern and / or a scan sequence and / or a scan speed and / or a scan duration of a scan pattern and / or a scan duration of a scan sequence and / or a pulse duration of pulses of an irradiation beam of the first and / or second wavelength and / or an irradiation beam profile of said irradiation beam and / or a radiation (photon) density and / or a radiation intensity and / or a radiation power and / or a radiation wavelength); temperature data of the current and / or predicted temperature of the intraocular lens during said exposure; Refractive index data of the refractive index of the intraocular lens to be acquired based on said exposure, in particular the refractive index data to be acquired relating to mapping of the refractive index to be acquired to specific positions / coordinates of the intraocular lens; rhexis dimension data of rhexis dimension, ocular data relating to the size and / or shape of the patient's eye; positioning data relating to the position and / or orientation of the intraocular lens relative to the eye; and It includes one or more of the following enrollment data regarding the identity of the patient and / or the patient's particular eye.

[0481] The present invention further relates to a method for locally adjusting the polarizability of an intraocular lens according to the present invention placed in a patient's eye, wherein exposing the intraocular lens to the radiation beam comprises exposing a first volume of the intraocular lens before exposing a second volume of the intraocular lens, the first volume being further away from the cornea of ​​the patient's eye than the second volume.

[0482] In the above clause, the first step of the method may be providing the intraocular lens.

[0483] In examples, exposing the intraocular lens to the irradiation beam may include exposing a first volume and / or plane and / or location of the intraocular lens before exposing a second volume and / or plane and / or location of the intraocular lens, the first volume and / or plane and / or location being further from the cornea of ​​the patient's eye than the second volume and / or plane and / or location, and the volume and / or plane and / or location irradiated at a later time point in the irradiation sequence may be closer to the cornea than the volume and / or plane and / or location irradiated at an earlier time point. The volume may thereby be associated with one or more planes of the intraocular lens.

[0484] The present invention further relates to a method for correcting the visual acuity of a patient by modifying the refractive index of an intraocular lens according to the present invention in the patient's eye, comprising: Identifying and measuring the patient's degree of vision correction; determining the location and type of refractive structures to be written into the intraocular lens to correct the patient's vision; Thereafter, exposing the intraocular lens to two-photon or multi-photon radiation having a wavelength of 600 nm to 800 nm to locally reduce the polarizability of the intraocular lens; and / or Thereafter, exposing the intraocular lens to two-photon or multi-photon radiation having a wavelength of 400 nm to 590 nm to locally increase the polarizability of the intraocular lens, preferably by using the systems and / or processes described above for exposing the intraocular lens to the radiation.

[0485] As outlined above, a change in polarizability leads to a change in the refractive index.

[0486] It should be noted that variations of the embodiments described in the present invention are covered by the scope of the present invention. Any feature disclosed in the present invention can be replaced with an alternative feature serving the same purpose or an equivalent or similar purpose, unless expressly excluded. Therefore, any feature disclosed in the present invention should be considered as a general series example or as an equivalent or similar feature, unless otherwise specified.

[0487] All features of the present invention can be combined with one another in any manner, unless certain features and / or steps are mutually exclusive. This is particularly true of preferred features of the present invention. Likewise, features of non-essential combinations can be used separately (and not in combination).

[0488] It should also be pointed out that many features, particularly those of the preferred embodiments of the present invention, are inventive in their own right and should not be considered solely as part of an embodiment of the present invention: independent protection may be sought for these features in addition to, or as an alternative to, any presently claimed invention.

[0489] The technical teachings disclosed in the present invention may be abstracted and combined with other embodiments.

[0490] Many other effective alternatives will no doubt occur to those skilled in the art. It will be understood that the invention is not limited to the described embodiments, but encompasses modifications which are obvious to those skilled in the art and which fall within the scope of the appended claims. [Example]

[0491] The following examples are intended to illustrate in a non-limiting manner the advantages of the present compounds.

[0492] Unless otherwise indicated, all syntheses are carried out under an inert atmosphere using dry (i.e., anhydrous) solvents. Solvents and reagents are purchased from commercial sources.

[0493] DCM is used to refer to dichloromethane. DMF is used to refer to dimethylformamide. EE or EtOAc is used to refer to ethyl acetate. THF is used to refer to tetrahydrofuran. RT means room temperature.

[0494] Copolymer properties can be investigated against blanks prepared by bulk polymerization of the monomers. Therefore, comonomers, crosslinkers, and initiators can be purchased from commercial sources. All chemicals are of the highest purity available and can be used as received.

[0495] Synthesis of intermediate materials: Example 1:

[0496] [ka]

[0497] 4-Methoxyphenylacetic acid (30.000 mmol; 1.00 equiv; 5.087 g) is suspended in acetic anhydride (302.400 mmol; 10.08 equiv; 30.872 g; 28.585 mL). Pyridine-3-carbaldehyde (30.00 mmol; 1.00 equiv; 3.246 g; 2.847 mL) and triethylamine (30.00 mmol; 1.00 equiv; 3.036 g; 4.181 mL) are then added. The reaction mixture is heated to 120 °C overnight. Water is added at 110 °C, and the mixture is stirred for 30 minutes before being cooled to room temperature. Volatiles are removed in vacuo. The crude mixture is purified by column chromatography using dichloromethane / methanol as the eluent. 3.3 g of (E)-2-(4-methoxy-phenyl)-3-pyridin-3-yl-acrylic acid are isolated as a beige solid (yield 45% of theory).

[0498] 1 H NMR(500MHz,DMSO-d6)δ 12.78(br s,1H),8.39(dd,J=4.8,1.6Hz,1H),8.32(d,J=2.2Hz,1H),7.72(s,1H),7.35(dt,J=8.0,1.8H z,1H),7.23(dd,J=8.0,4.8Hz,1H),7.09(d,J=8.7Hz,2H),6.94(d,J=8.8Hz,2H),3.78(s,3H).

[0499] Similarly, other derivatives are prepared in the same way. R1 means reactant, R2 means reactant 2, and [P] means product.

[0500] [Table 4]

[0501] [ka]

[0502] 1H NMR(500MHz,DMSO-d6)δ 12.65(s,1H),8.01(d,J=2.4Hz,1H),7.73(s,1H),7.44-7.34(m,3H),7.22-7 .15(m,2H),7.11(dd,J=8.8,2.5Hz,1H),6.61(d,J=8.7Hz,1H),3.80(s,3H).

[0503] Example 2:

[0504] [ka]

[0505] (E)-2-(4-Methoxy-phenyl)-3-pyridin-3-yl-acrylic acid (11.61 mmol, 1.00 equiv.; 2.964 g) is suspended in dry dichloromethane (952.125 mmol; 82.0 equiv.; 60.80 mL). The suspension is then cooled in an ice bath, and meta-chloroperoxybenzoic acid (13.93 mmol; 1.20 equiv.; 3.123 g) is added. The reaction mixture is allowed to warm to room temperature with stirring overnight. The suspension is filtered, and the collected solid is washed twice with diethyl ether and dried in vacuo. 2.83 g (E)-2-(4-Methoxy-phenyl)-3-(1-oxy-pyridin-3-yl)-acrylic acid is isolated as a colorless solid (90% yield of theory).

[0506] 1 H NMR(500MHz,DMSO-d6)δ 12.96(s,1H),8.05(d,J=7.0Hz,1H),7.92(s,1H),7.60(s,1H),7.25(dd, J=7.9,6.6Hz,1H),7.11(d,J=8.7Hz,2H),7.02-6.85(m,3H),3.78(s,3H).

[0507] Similarly, other derivatives are prepared in the same manner.

[0508] [Table 5]

[0509] [ka]

[0510] 1 H NMR(500MHz,DMSO-d6)δ 12.86(s,1H),7.93(d,J=2.0Hz,1H),7.63(s,1H),7.44-7.38(m,3H),7.21-7 .19(m,2H),7.04(d,J=8.8Hz,1H),6.86(dd,J=8.8,2.1Hz,1H),3.90(s,3H).

[0511] Example 3:

[0512] [ka]

[0513] (E)-2-(4-Methoxyphenyl)-3-(1-oxy-pyridin-3-yl)-acrylic acid (9.37 mmol; 1.00 equiv; 2.54 g) is suspended in acetic anhydride (618.72 mmol; 66.00 equiv; 63.164 g; 58.49 mL). Sodium carbonate (28.12 mmol; 3.00 equiv; 3.89 g) and distilled water (65.62 mmol; 7.00 equiv; 1.182 g; 1.182 mL) are then added. Gas evolution is visible, and the reaction mixture is stirred overnight at 130°C. The reaction mixture solidifies upon cooling to room temperature. Distilled water is added. The suspension is filtered and washed several times with water. The solid is dried under vacuum. 2.1 g of 3-(4-methoxy-phenyl)-pyrano[2,3-b]pyridin-2-one are isolated as a greyish-beige solid (yield 89% of theory).

[0514] 1H NMR(500MHz,chloroform-d)δ 8.51(dd,J=4.8,1.8Hz,1H),7.91(dd,J=7.6,1.8Hz,1H),7.74(s,1H),7.69(d, J=8.8Hz,2H),7.31(dd,J=7.5,4.8Hz,1H),6.98(d,J=8.8Hz,2H),3.86(s,2H).

[0515] Similarly, other derivatives are prepared in the same manner.

[0516] [Table 6]

[0517] Example 4:

[0518] [ka]

[0519] 3-(4-Methoxy-phenyl)-pyrano[2,3-b]pyridin-2-one (7.42 mmol; 1.00 equiv; 1.88 g) is suspended in 50 mL of dry dichloromethane and the solution is cooled in an ice bath. Boron tribromide (8.91 mmol; 1.20 equiv; 2.23 g; 0.85 mL) dissolved in 10 mL of DCM is then added dropwise. The solution is allowed to warm to room temperature overnight, and the reaction mixture is quenched with water. The suspension is filtered, and the solid is washed several times with water. The crude solid is recrystallized using acetone and ethanol. 1.2 g of 3-(4-hydroxy-phenyl)-pyrano[2,3-b]pyridin-2-one is isolated as a light gray solid (68% yield of theory).

[0520] 1 H NMR(500MHz,DMSO-d6)δ 9.79(s,1H),8.49(dd,J=4.8,1.9Hz,1H),8.23(dd,J=7.6,1.9Hz,1H),8.18(s, 1H),7.60(d,J=8.7Hz,2H),7.46(dd,J=7.6,4.8Hz,1H),6.86(d,J=8.7Hz,2H).

[0521] Example 5:

[0522] [ka]

[0523] 3-(4-Hydroxy-phenyl)-pyran[2,3-b]pyridin-2-one (1.2 g, 5.02 mmol, 1.00 equiv.) was refluxed with a solution of potassium carbonate (2.81 g, 20.07 mmol, 4.00 equiv.) and 12-bromo-dodecan-1-ol (1.43 g, 5.27 mmol, 1.05 mmol) in acetone (40 mL) for a minimum of 2 days. The suspension was filtered and the filtrate solvent was evaporated. The crude residue was recrystallized from acetone and n-butanol to give 0.685 g of 3-[4-(12-hydroxy-dodecyloxy)-phenyl]-pyran[2,3-b]pyridin-2-one (32% yield of theory).

[0524] 1 H NMR(500MHz,DMSO-d6)δ 8.50(dd,J=4.8,1.8Hz,1H),8.24(d,J=6.1Hz,2H),7.70(d,J=8.8Hz,2H),7.48(dd,J=7.5,4.8Hz,1H),7.03(d,J=8.8Hz,2H),4.30(t,J= 5.1Hz,1H), 4.02(t,J=6.5Hz,2H),3.36(td,J=6.5,4.9Hz,2H),1.73(p,J=6.6Hz,2H),1.41(dt,J=12.1,5.6Hz,5H),1.34-1.22(m,17H).

[0525] Preparation of compounds according to the invention Example 6.1:

[0526] [ka]

[0527] 3-[4-(12-Hydroxy-dodecyloxy)-phenyl]-pyran[2,3-b]pyridin-2-one (0.67 g, 1.58 mmol, 1.00 equiv.) was dissolved in dry THF (60 mL) and triethylamine (0.88 mL, 6.33 mmol, 4.00 equiv.) was added. Acryloyl chloride (0.161 mL, 1.9 mmol, 1.20 equiv.) was then added at 0 °C and stirred at room temperature until the reaction was complete. The reaction was quenched with 2-propanol (0.25 mL), the suspension was filtered, and the solvent of the filtrate was removed. The crude product was purified by column chromatography using CHCl3 / MeOH as the eluent. The synthesis yields 0.375 g of acrylic acid 12-[4-(2-oxo-2H-pyrano[2,3-b]pyridin-3-yl)-phenoxy]-dodecyl ester (49% of theory).

[0528] 1 H NMR (500MHz,chloroform-d)δ 8.50(dd,J=4.8,1.8Hz,1H),7.91(dd,J=7.6,1.8Hz,1H),7.73(s,1H),7.68(d,J=8.8Hz,2H), 7.30(dd,J=7.6,4.8Hz,1H),6.97(d,J=8.8Hz,2H),6.39(dd,J=17.3,1.4Hz,1H),6.12(dd,J=1 7.3,10.4Hz,1H),5.81(dd,J=10.4,1.4Hz,1H),4.15(t,J=6.8Hz,2H),4.01(t,J=6.6Hz,2H),1 .80(dt,J=14.5,6.6Hz,2H),1.67(p,J=6.8Hz,2H),1.46(q,J=7.5Hz,2H),1.39-1.25(m,17H). mp(DSC):109℃ Absorption maximum (UV-Vis): 347 nm

[0529] Similarly, other derivatives are prepared in the same manner.

[0530] [Table 7]

[0531] Compound 6a: 1 H NMR(500MHz,DMSO-d6)δ 8.61(s,1H),8.24(d,J=0.7Hz,1H),7.70-7.67(m,2H),7.48-7.44(m,2H),7.43-7. 40(m,1H),6.83(s,1H),6.30(dd,J=17.3,1.6Hz,1H),6.16(dd,J=17.3,10.3Hz,1H ),5.92(dd,J=10.3,1.6Hz,1H),4.34(t,J=6.6Hz,2H),4.08(t,J=6.7Hz,2H),1.73 (p,J=6.8Hz,2H),1.59(p,J=6.7Hz,2H),1.40(p,J=6.9Hz,2H),1.35-1.21(m,16H). Melting point (DSC):88.2℃ Maximum absorption (UV-Vis): 328nm

[0532] Compound 6b: 1 H NMR(500MHz,クロロホルム-d)δ 7.68(s,1H),7.60-7.56(m,2H),7.48(s,1H),7.45-7.37(m,3H),6.39(dd,J=17.3,1.5Hz,1H),6.35(s,1H),6.11(dd,J=17.3,10.4Hz,1H ),5.81(dd,J=10.4,1.5Hz,1H),4.14(t,J=6.7Hz,2H),4.04-3.97(m,2H),1.78(p,J=7.4Hz,2H),1.69-1.62(m,2H),1.38-1.24(m,17H). Melting point (DSC):87.3℃ Maximum absorption (UV-Vis): 359nm

[0533] Example 6.2:

[0534]

change

[0535] 3-(3,5-Difluorophenyl)-7-[(11-hydroxyundecyl)oxy]-2H-pyrano[2,3-b]pyridin-2-one (0.15 g, 0.348 mmol, 1.00 equiv.) was dissolved in DCM (10 mL) and triethylamine (193 μL, 1.392 mmol, 4.00 equiv.). 4-(Dimethylamino)pyridine (9 mg, 0.07 mmol, 0.20 equiv.) and methacrylic anhydride (30 μL, 0.418 mmol, 1.20 equiv.) were added at 0°C. After stirring at room temperature for 1 day, additional methacrylic anhydride was added (66.2 μL, 0.189 mmol, 0.60 equiv.). The reaction was stirred for another day until the reaction was complete. The reaction mixture is concentrated in vacuo and subjected to column chromatography using cyclohexane / chloroform as the eluent. The synthesis yields 0.108 g of 11-{[3-(3,5-difluorophenyl)-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl]oxy}undecyl 2-methylprop-2-enoate (0.21 mmol, 66% of theory).

[0536] 1 H NMR(500MHz,DMSO-d6)δ 8.45(s,1H),8.13(d,J=8.4Hz,1H),7.54-7.48(m,2H),7.31(tt,J=9.3,2 .4Hz,1H),6.92(d,J=8.4Hz,1H),6.00(d,J=1.5Hz,1H),5.65(t,J=1.7Hz, 1H),4.35(t,J=6.6Hz,2H),4.07(t,J=6.6Hz,2H),1.87(s,3H),1.75(p,J= 6.8Hz, 2H), 1.60 (p, J=6.8Hz, 2H), 1.44-1.37 (m, 2H), 1.35-1.22 (m, 12H). 19 F NMR (470MHz, DMSO-d6)δ-110.0. mp(DSC):102℃ Absorption maximum (UV-Vis): 347 nm

[0537] Synthesis of precursor materials: Example 7:

[0538] [ka]

[0539] 2,4-Dimethoxypyridine (15.00 g; 103.48 mmol; 1.00 equiv.) is added to dry acetonitrile (140.53 mL; 2.69 mol; 26.00 equiv.) and N-bromosuccinimide (18.60 g; 103.48 mmol; 1.00 equiv.). The reaction mixture is refluxed overnight until the reaction is complete. The solvent is removed under reduced pressure, and the crude product is purified by column chromatography using heptane / ethyl acetate as the eluent. 16.65 g of 5-bromo-2,4-dimethoxypyridine (74% yield of theory) is isolated along with 4.42 g of 3-bromo-2,4-dimethoxypyridine (20% yield of theory) as a by-product.

[0540] 1 H NMR (500MHz, DMSO-d6) δ 8.15 (s, 1H), 6.53 (s, 1H), 3.89 (s, 4H), 3.83 (s, 3H).

[0541] Similarly, other derivatives are prepared in the same manner.

[0542] [Table 8]

[0543] Compound 7a: 1 H NMR (500MHz, chloroform-d) δ 7.99(dd,J=5.7,2.1Hz,1H),6.52(dd,J=5.8,2.0Hz,1H),4.00(d,J=1.9Hz,3H),3.94(d,J=2.1Hz,3H).

[0544] Compound 7c: 1 H NMR (500 MHz, chloroform-d) δ 7.69 (dd, J=2.4 Hz), 6.73 (dd, J=2.4 Hz), 3.89 (s, 3H), 3.87 (s, 3H).

[0545] Compound 7d: 1 H NMR (500 MHz, chloroform-d) δ 6.73 (s, 2H), 3.94 (s, 6H).

[0546] Example 8:

[0547] [ka]

[0548] A 2M solution of n-butyllithium in hexanes (10 mL, 20 mmol, 1.0 equiv.) was added via syringe over 1 min to a cooled (0 °C) and stirred mixture of a 2M solution of isopropylmagnesium chloride in THF (5 mL, 10 mmol, 0.5 equiv.) and anhydrous THF (52 mL) in a Schlenk flask under argon. The mixture was stirred for 5 min to give a yellow solution that was cooled to -2 to 0 °C. A solution of 5-bromo-2,4-dimethoxypyridine (4.361 g, 20 mmol, 1.0 equiv.) in 15 mL of anhydrous THF was added via syringe, and the resulting solution was stirred at -2 to 0 °C for 45 min. N,N-dimethylformamide (4.65 mL, 3.0 equiv.) was then added, and the mixture was continuously stirred at 0 °C for 30 min, then at room temperature for 45 to 60 min. Saturated aqueous NH4Cl was added, and the aqueous layer was separated and then extracted with EtOAc. The combined organic layers are dried over MgSO4, filtered, concentrated in vacuo, and purified by recrystallization using a mixture of methanol and distilled water to give 2.57 g of 4,6-dimethoxy-pyridine-3-carbaldehyde as a yellow crystalline solid (78% yield of theory).

[0549] 1 H NMR (500 MHz, chloroform-d) δ 10.23 (s, 1H), 8.54 (s, 1H), 6.22 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H).

[0550] Similarly, other derivatives are prepared in the same manner.

[0551] [Table 9]

[0552] Compound 8b: 1 H NMR (500 MHz, chloroform-d) δ 10.42 (s, 1H), 8.19 (d, J = 6.0 Hz, 1H), 6.58 (d, J = 6.0 Hz, 1H), 4.02 (s, 3H), 3.95 (s, 4H).

[0553] Compound 8c: 1 H NMR (500 MHz, chloroform-d) δ 10.20 (s, 1H), 8.09 (d, J = 2.3 Hz, 1H), 6.81 (d, J = 2.3 Hz, 1H), 3.97 (s, 4H), 3.96 (s, 4H).

[0554] Example 9:

[0555] [ka]

[0556] To a solution of phenacyltriphenylphosphonium bromide (21.71 g, 42.35 mmol, 1.20 equiv.) and triethylamine (5.91 mL; 42.35 mmol, 1.20 equiv.) in anhydrous tetrahydrofuran (143.62 mL; 50.00 equiv.) is added 4,6-dimethoxypyridine-3-carbaldehyde (5.90 g, 35.30 mmol, 1.00 equiv.) at 0 °C. The solution is slowly warmed to room temperature and then refluxed until complete. Saturated aqueous NH4Cl is added, the aqueous layer is separated, and then extracted with EtOAc. The combined organic layers are dried over MgSO4, filtered, concentrated in vacuo, and purified by column chromatography on silica gel using heptane / ethyl acetate. 7.2 g of (E)-3-(4,6-dimethoxypyridin-3-yl)-1-phenylprop-2-en-1-one were isolated as a red solid (yield 76% of theory).

[0557] 1 H NMR(500MHz,chloroform-d)δ 8.29(s,1H),8.02-7.99(m,2H),7.85(d,J=15.8Hz,1H),7.69(d,J=15.8Hz,1H),7.6 0-7.55(m,1H),7.50(dd,J=8.2,6.8Hz,2H),6.26(s,1H),3.97(s,3H),3.95(s,3H).

[0558] Similarly, other derivatives are prepared in the same manner, where R1 and R2 are the starting materials and [P] is the product of the reaction.

[0559] [Table 10]

[0560] [P] in Example 9a 1 H NMR(500MHz,chloroform-d)δ 8.03-7.98(m,2H),7.92(d,J=15.7Hz,1H),7.79(d,J=8.2Hz,1H),7.58-7.54(m,2 H),7.49(dd,J=8.3,6.9Hz,2H),6.37(d,J=8.2Hz,1H),4.06(s,3H),3.97(s,3H).

[0561] Example 10:

[0562] [ka]

[0563] (E)-3-(4,6-Dimethoxypyridin-3-yl)-1-phenylprop-2-en-1-one (7.76 g; 28.82 mmol, 1.00 equiv.) was dissolved in methanol (46.75 mL; 40.00 equiv.) and tetrahydrofuran (46.69 mL; 20.00 equiv.) and cooled to 0 °C. Sodium hydroxide pellets (1.15 g; 28.82 mmol, 1.00 equiv.) were dissolved in methanol, followed by the addition of hydrogen peroxide (11.67 mL, 115.26 mmol, 4.00 equiv., 30 wt.% aqueous solution). After 0.5 h, 0.25 mL of THF was added to dissolve the precipitate. The reaction mixture was stirred at 0 °C for 3 h and then at room temperature overnight. The mixture was diluted with saturated NaHCO3 and water. The aqueous phase was extracted three times with tert-butyl methyl ether. The organic layer was washed with saturated NaCl and dried over MgSO. The crude product was purified by dissolving in hot THF followed by the addition of heptane. The precipitate formed was filtered and washed with heptane to give 5.13 g of 5-(3-benzoyloxiran-2-yl)-2,4-dimethoxypyridine (63% yield of theory).

[0564] 1 H NMR(500MHz,chloroform-d)δ 8.07-8.03(m,2H),7.99(d,J=0.7Hz,1H),7.65-7.60(m,1H),7.53-7.48(m,2H),6.22 (s,1H),4.30(d,J=2.0Hz,1H),4.22(dd,J=2.0,0.7Hz,1H),3.94(s,3H),3.84(s,3H).

[0565] Example 11:

[0566] [ka]

[0567] 5-(3-Benzoyloxiran-2-yl)-2,4-dimethoxypyridine (5.13 g; 17.98 mmol, 1.00 equiv.) is placed in a flask and ethanol (52.49 mL, 50.00 equiv.) (saturated with sodium hydroxide) is added. The mixture is refluxed for 2 hours. The solvent is then removed under reduced pressure, and water is added to the residue. The aqueous phase is extracted with tert-butyl methyl ether. The aqueous phase is then acidified to pH 2 with 2 M HCl, followed by dilution with an equal volume of saturated NaCl solution. The solution is then extracted 10 times with THF. The combined organic layers are dried over MgSO4, filtered, concentrated in vacuo, and purified via column chromatography on silica gel using dichloromethane / methanol / AcOH as the eluent. 3.9 g of 3-(4,6-dimethoxypyridin-3-yl)-2-hydroxy-2-phenylpropanoic acid is isolated (72% yield of theory).

[0568] 1 H NMR(500MHz,DMSO-d6)δ 12.13(br s,1H),7.90(s,1H),7.47-7.4fd5(m,2H),7.29(dd,J=8.4,6.7Hz,2H),7.25-7.22(m,1H),6.57(s,1H),5.88(br s, 1H), 3.97 (s, 3H), 3.72 (s, 3H), 3.28 (dd, J=14.5Hz, 2H).

[0569] Example 12:

[0570] [ka]

[0571] 3-(4,6-Dimethoxypyridin-3-yl)-2-hydroxy-2-phenylpropanoic acid (100.00 mg; 0.33 mmol, 1.00 equiv.) was reduced in a mixture of hydroiodic acid (0.92 mL; 6.97 mmol; 21.14 equiv.; 57% by weight) and acetic acid (4.56 mL; 79.79 mmol, 242.00 equiv.) for 1 hour and then poured onto ice. The aqueous phase was extracted four times with DCM, and the combined organic phases were dried over MgSO4. The crude product was purified by column chromatography on silica gel using DCM / methanol to give 17 mg of 7-hydroxy-3-phenyl-2H-pyrano[3,2-c]pyridin-2-one (22% yield of theory).

[0572] 1 H NMR(500MHz,DMSO-d6)δ 8.13(s,1H),7.98(s,1H),7.60(dd,J=7.3,1.7Hz,2H),7.43(dd,J=8.3,6.6Hz,2H),7.40-7.36(m,1H),6.11(s,1H).

[0573] Example 13:

[0574] [ka]

[0575] 2,6-Dimethoxypyridine-3-carboxaldehyde (1.73 g, 10.35 mmol, 1.00 equiv.) was refluxed overnight at 130 °C with potassium acetate (0.772 g, 7.87 mmol, 0.76 equiv.), phenylacetic acid (1.42 g; 10.35 mmol, 1.00 equiv.), and acetic anhydride (14.26 mL; 13.5 equiv.). After cooling to room temperature, water was added and the mixture was stirred for 30 minutes. The precipitate was filtered and recrystallized from 2-propanol. 0.435 g of 7-methoxy-3-phenyl-2H-pyrano[2,3-b]pyridin-2-one was isolated (yield: 19% of theory).

[0576] 1H NMR(500MHz,DMSO-d6)δ 8.27(s,1H),8.15(d,J=8.4Hz,1H),7.73-7.68(m,2H),7.49-7.44(m,2H),7.43-7.38(m,1H),6.92(d,J=8.3Hz,1H),3.96(s,3H).

[0577] Similarly, other derivatives are prepared in the same manner, where R1 and R2 are the starting materials and [P] is the product of the reaction.

[0578] [Table 11-1]

[0579] [Table 11-2]

[0580] [Table 11-3]

[0581] [Table 11-4]

[0582] [Table 11-5]

[0583] [ka]

[0584] 1 H NMR(500MHz,DMSO-d6)δ 8.54(dd,J=4.8,1.8Hz,1H),8.31(s,1H),8.27(dd,J=7.6,1.9Hz,1H),7.77-7.66(m,2H),7.55-7.40(m,4H).

[0585]

change

[0586] 1 H NMR (500MHz, クロロホルム-d)δ 8.41(s,1H),7.79(d,J=0.8Hz,1H),7.71-7.61(m,2H),7.47-7.38(m,3H),6.65(s,1H),4.03(s,3H).

[0587]

change

[0588] 1 H NMR(500MHz, DMSO-d6)δ 8.66(s,1H),8.20(s,1H),7.79-7.71(m,2H),7.57(d,J=8.7Hz,1H),6.92(s,1H),3.96(s,3H).

[0589]

change

[0590] 1 H NMR (500MHz, DMSO-d6)8.98(s,1H),8.67(d,J=5.7Hz,1H),8.33(s,1H),7.75-7.70(m,2H),7.51-7.43(m,4H).

[0591]

change

[0592] 11H NMR (500 MHz, DMSO-d6) δ 8.13 - 8.10 (m, 1H), 7.97 (d, J = 5.8 Hz, 1H), 7.52 (s, 1H), 7.19 (dd, J = 5.3, 1.9 Hz, 3H), 6.98 - 6.96 (m, 2H), 6.63 (d, J = 5.9 Hz, 1H), 3.56 (s, 5H), 3.51 (s, 5H).

[0593]

Chem.

[0594] 1 1H NMR (500 MHz, DMSO-d6) δ 8.97 (s, 1H), 8.73 (d, J = 5.7 Hz, 1H), 8.17 (s, 1H), 7.88 (dd, J = 8.0, 1.3 Hz, 1H), 7.81 - 7.78 (m, 1H), 7.71 (tt, J = 7.7, 1.1 Hz, 1H), 7.60 (d, J = 7.5 Hz, 1H), 7.54 (d, J = 5.7 Hz, 1H).

[0595]

Chem.

[0596] 1 1H NMR (500 MHz, DMSO-d6) δ 8.97 (s, 1H), 8.66 (d, J = 5.7 Hz, 1H), 8.30 (s, 1H), 7.64 (d, J = 8.2 Hz, 2H), 7.47 (d, J = 5.7 Hz, 1H), 7.30 (d, J = 7.9 Hz, 2H), 2.36 (s, 3H).

[0597]

Chem.

[0598] 1 1H NMR (500 MHz, DMSO-d6) δ 8.67 (s, 1H), 8.39 (s, 1H), 7.73 (d, J = 8.2 Hz, 2H), 7.40 (d, J = 8.0 Hz, 2H), 6.90 (s, 1H), 3.97 (s, 3H).

[0599] 19 F NMR (470MHz, DMSO-d6) δ -60.9.

[0600]

change

[0601] 1 H NMR(500MHz,DMSO-d6)δ 8.41(s,1H),7.95(d,J=8.1Hz,1H),7.84(d,J=8.3Hz,1H),7.78(d,J=8.0Hz,2H),7.39(d,J=7.9Hz,2H),3.95(s,3H).

[0602]

change

[0603] 1 H NMR(500MHz,DMSO-d6)δ 8.46(s,1H),8.14(d,J=8.4Hz,1H),7.51(d,2H,J=9.0Hz),7.31(tt,J=9.3,2.4Hz,1H),6.95(d,J=8.4Hz,1H),3.97(s,3H).

[0604] 19 F NMR (470MHz, DMSO-d6) δ -110.0.

[0605]

change

[0606] 1H NMR(500MHz,DMSO-d6)δ 8.43(s,1H),8.17(t,J=1.7Hz,1H),8.15(d,J=8.4Hz,1H),8.10-8.06(m,1H),7.89 (dt,J=7.8,1.3Hz,1H),7.69(t,J=7.9Hz,1H),6.95(d,J=8.4Hz,1H),3.97(s,3H).

[0607] Example 14:

[0608] [ka]

[0609] 0.446 g (1.7 mmol) of 3-[4-bromo-2-(trifluoromethoxy)phenyl]-7-methoxy-2H-pyrano[3,2-c]pyridin-2-one), 0.152 g (1.29 mmol, 1.2 equivalents) of n-pentylboronic acid, and 0.524 g (2.27 mmol, 2.1 equivalents) of potassium phosphate trihydrate were dissolved in 3 mL of toluene and degassed three times. 9.92 mg (0.043 mmol, 0.04 equivalents) of palladium(II) acetate and 35.92 mg (0.086 mmol; 0.08 equivalents) of 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl were added. The reaction mixture was then stirred under a protective gas atmosphere at 90 °C for 2 hours. The cooled solution is diluted with 2-methyltetrahydrofuran and water, and the phases are separated. The aqueous phase is extracted three times with 2-methyltetrahydrofuran, and the organic phase is dried over MgSO4 and evaporated. The crude product is purified by column chromatography on silica gel. 0.26 g of 7-methoxy-3-[4-pentyl-2-(trifluoromethoxy)phenyl]-2H-pyrano[3,2-c]pyridin-2-one is isolated (60% of theory).

[0610] 1H NMR(500MHz,chloroform-d)δ 8.38(s,1H),7.71(d,J=0.8Hz,1H),7.38(d,J=7.7Hz,1H),7.19-7.16(m,2H),6.66(s,1H),4.03(s, 3H),2.69-2.64(m,2H),1.65(dq,J=9.6,7.3Hz,2H),1.35(tt,J=6.7,2.4Hz,4H),0.92-0.90(m,3H).

[0611] Similarly, other derivatives are prepared in the same manner, where R1 and R2 are the starting materials and [P] is the product of the reaction.

[0612] [Table 12]

[0613] Example 15:

[0614] [ka]

[0615] To a solution of 7-methoxy-3-phenyl-2H-pyrano[3,2-c]pyridin-2-one (0.5 g; 1.974 mmol) in 4 mL of anhydrous N,N-dimethylformamide, anhydrous lithium chloride (0.418 g; 9.87 mmol, 5.0 equiv.) and para-toluenesulfonic acid monohydrate (1.88 g; 9.87 mmol, 5.0 equiv.) were added. The reaction mixture was stirred at 180°C for 2 hours. Water was added at room temperature to form a precipitate, which was filtered and extracted again three times with DCM. The combined organic solids were dried in vacuo to give 0.376 g of 3-phenyl-2H,6H,7H-pyrano[3,2-c]pyridine-2,7-dione (80% yield of theory).

[0616] 1H NMR (500MHz, DMSO-d6)δ 12.34(br s,1H),8.13(s,1H),7.98(s,1H),7.63-7.57(m,2H),7.46-7.41(m,2H),7.41-7.36(m,1H),6.13(s,1H).

[0617] The same method as the inducer, the same method as the modulation method.

[0618] Table 13

[0619] Compound 15b: 1 H NMR(500MHz,DMSO-d6)δ 12.40(s,1H),8.16(s,1H),7.85(s,1H),7.41(d,J=7.8Hz,1H),7.30(dd,J=7.9,1.6Hz,1H),7.25(d,J=2.2Hz,1H),6.1 6(s,1H),2.66(t,J=7.7Hz,2H),1.60(p,J=7.5Hz,2H),1.30(ddq,J=16.4,7.3,4.5,2.6Hz,4H),0.86(t,J=6.9Hz,3H).

[0620] Compound 15c: 1 H NMR(500MHz,DMSO-d6)δ 12.34(br s,1H),8.40(s,1H),8.04(d,J=8.4Hz,1H),7.52-7.47(m,2H),7.29(tt,J=9.3,2.4Hz,1H),6.70(br s,1H).

[0621] Compound 15d: 1 H NMR(500MHz,DMSO-d6)δ 12.28(br s,1H),8.38(s,1H),8.15(t,J=1.7Hz,2H),8.08-8.03(m,1H),7.86(dt,J=7.7,1.4Hz,1H),7.68(t,J=7.8Hz,1H)6.71(br s,1H).

[0622] Example 16:

[0623] [ka]

[0624] 3-Phenyl-2H,6H,7H-pyrano[3,2-c]pyridine-2,7-dione (2.0 g, 8.36 mmol, 1.00 equiv.) was refluxed with a solution of potassium carbonate (4.67 g, 33.00 mmol, 4.00 equiv.) and 12-bromo-dodecan-1-ol (2.337 g, 8.79 mmol, 1.05 mmol) in N,N-dimethylformamide (35 mL) for a minimum of 2 days. The suspension was filtered and the filtrate's solvent was evaporated. The crude residue was purified by column chromatography using DCM / methanol and / or heptane / ethyl acetate as eluents. 0.628 g of 7-[(12-hydroxydodecyl)oxy]-3-phenyl-2H-pyrano[3,2-c]pyridin-2-one (yield 18% of theory) is isolated as a by-product together with 1.95 g of 6-(12-hydroxydodecyl)-3-phenyl-2H,6H,7H-pyrano[3,2-c]pyridine-2,7-dione (yield 55% of theory).

[0625] [ka]

[0626] 1 H NMR(500MHz,DMSO-d6)δ 8.61(s,1H),8.24(s,1H),7.69(d,J=7.9Hz,2H),7.48-7.40(m,3H),6.82(s,1H),4.35-4.30(m,3H) ),3.38-3.34(m,2H),1.73(p,J=6.8Hz,2H),1.39(dq,J=12.5,6.3,5.0Hz,4H),1.34-1.21(m,14H).

[0627] [ka]

[0628] 1 H NMR(500MHz,DMSO-d6)δ 8.44(s,1H),7.91(s,1H),7.61-7.59(m,2H),7.46-7.43(m,2H),7.40-7.37(m,1H),6.21(s,1H),4.31(t,J=5.1Hz,1 H),3.97(t,J=7.3Hz,2H),3.38-3.34(m,2H),1.67(q,J=7.1Hz,2H),1.38(p,J=6.8Hz,2H),1.25(d,J=21.5Hz,16H).

[0629] Similarly, other derivatives are prepared in the same manner, where R1 and R2 are the starting materials and [P] is the product of the reaction.

[0630] [Table 14]

[0631] [ka]

[0632] 1 H NMR(500MHz,DMSO-d6)δ 8.45(s,1H),8.12(d,J=8.4Hz,1H),7.51(dd,J=9.0,2.2Hz,2H),7.31(tt,J=9.3,2.4Hz,1H),6.92(d,J=8.4Hz,1H),4.35(t,J=6.6 Hz,2H),4.31(t,J=5.1Hz,1H),3.36(td,J=6.6,5.2Hz,2H),1.75(p,J=6.8Hz,2H),1.39(p,J=7.2,6.3Hz,4H),1.34-1.21(m,12H).

[0633] [ka]

[0634] 1H NMR(500MHz,DMSO-d6)δ 7.97(s,1H),7.85-7.79(m,3H),7.72(d,J=1.7Hz,1H),7.61(t,J=7.9Hz,1H),7.53-7.49(m,1H),4.59-4.54(m,5H) ),4.48-4.43(m,2H),4.36-4.33(m,2H),4.32-4.27(m,2H),3.76(t,J=4.8Hz,2H),3.41(dt,J=10.5,5.3Hz,4H).

[0635] Example 17: The photochemistry of 3-phenyl-coumarin containing polymethacrylates is described by characterization of the compounds / monomers according to the present invention via melting points and comparison with the reference material Ref-[1] as disclosed in M. Schraub et al, European Polymer Journal 51 (2014) 21-27.

[0636] [Table 15]

[0637] Examples of uses: Example 18 - General polymerization procedure for preparing bulk copolymer For the production of bulk polymer blanks, the monomers are melted under vacuum in the amounts and additional ingredients as shown in Table 3 below.

[0638] The compositions shown in Table 3 are formulated in the same manner as described, after mixing all compounds together with stirring. If necessary, use a heating bath for stirring. These formulations are also the basis for the copolymers compared in Table 5.

[0639] Table 3: Composition - Amounts of components are given in mol%, and the amount of each selected radical initiator adds up to 100 mol%.

[0640] [Table 16] n-BuAc = n-butyl acrylate, EGDMA = ethylene glycol dimethacrylate, HEMA = hydroxyethyl methacrylate, EtMAc = ethyl methacrylate. a Octadecane-1,18-diyl diacrylate is used instead of EGDMA. b 8-methylnonyl acrylate is used instead of n-butyl acrylate. c Poly(ethylene glycol) diacrylate (M) was used instead of EGDMA. n 250).

[0641] Illustratively, a composition of 12-({2-oxo-3-phenyl-2H-pyrano[3,2-c]pyridin-7-yl}oxy)dodecylprop-2-enoate (A-097) (0.2 g, 0.42 mmol, 22.5 mol%) as a crosslinker, n-butyl acrylate (0.17 g, 1.31 mmol, 70.4 mol%), and ethylene glycol dimethacrylate (0.02 g, 0.10 mmol, 5.4 mol%) (EGDMA) was thoroughly mixed under stirring using mild heat and degassed by three freeze-pump cycles. An appropriate amount (0.02-0.12 equivalents) of a radical initiator (e.g., 1,1'-(3,3,5-trimethylcyclohexylidene)bis[2-(1,1-dimethylethyl)-peroxide [Luperox® 231] or 2-[(E)-2-(1-cyano-1-methylethyl)diazen-1-yl]-2-methylpropanenitrile) is added.

[0642] Two glass plates are coated with polyethylene sheets, and a silicone rubber gasket is used to create a 1 mm thick cell between the polyethylene sheets. The coated surfaces of the glass sheets are clipped together using a spring clip, with a syringe needle placed between the gasket and the polyethylene sheet. The cavity is then filled with the formulation described above or the formulation further shown in Table 3 through the needle using a gas-tight syringe. Once the cavity is filled, the syringe needle is removed, and a final clip is used to seal the mold, and the assembly is placed in an oven. The polymerization temperature is between 60°C and 180°C. Individual polymerization conditions are selected for each initiator and can be determined by those skilled in the art based on the formulation mixture. The mold is allowed to cool to room temperature before the polymer plate is removed from the mold.

[0643] A change in the refractive index is induced by irradiation at 340-365 nm. The refractive index (n) of the blank at 590 nm is measured with a Schmidt+Haensch AR12 before and after irradiation. The table below shows the refractive index after irradiation as well as the change in refractive index (maximum Δn).

[0644] The phase transition temperatures are determined with a TA Instruments Q2000 differential scanning calorimeter during heating from −100° C. to 200° C. at 20 K / min in a second heating in an airtight aluminum pan.

[0645] [Table 17]

[0646] The results of Application Examples 18-5 to 18-8 show a significant change in refractive index after irradiation.

[0647] Furthermore, the addition of nitrogen within the photoactive chromophore according to the present invention significantly affects the optical properties relative to prior art compounds. This effect is illustrated by the preparation and comparison of homopolymers of representative prior art monomers (Ref-[1], Ref-[2], Ref-[3], and Ref-[4]) and monomers A-001, A-097, A-126, and A-046.

[0648] Ref-[2] is a monomer (compound (M-1)) as disclosed in WO 2017 / 032442.

[0649] Ref-[3] is a monomer as disclosed in WO 2017 / 032442 (compound (M-42)).

[0650] Ref-[4] is a monomer as disclosed in WO 2017 / 032442 (compound (M-53)).

[0651] This effect and direct comparison can be seen from the data in Table 5 and visualized in Figure 1.

[0652] [Table 18] a means the ratio of photoactive chromophore (mmol) to the total amount of the compounded mixture (in grams).

[0653] The ratio of photoactive chromophore (mmol) per total amount (gram) of the formulation mixture is calculated as follows: A composition according to Table 3 consists of the various components as described. The weights in grams of all of the components in each formulation are summed. The amount of each photoactive chromophore in mmol in each formulation (amount of Ref-[1], Ref-[2], Ref-[3], Ref-[4], A-001, A-097, A-126, or A-046) is then divided by the previously calculated total for that formulation containing that individual photoactive chromophore. The quotient of this mathematical operation is the specific photoactive chromophore (mmol) per total amount (gram) of the formulation mixture.

[0654] The aforementioned advantages of the compounds listed in Table 5 are visualized in Figure 1, where the refractive index change Δn is plotted against the amount of mmol photoactive chromophore per total amount of formulation in grams. Figure 1 shows that the examples according to the invention exhibit a higher refractive index change and a partially increased higher refractive index onset, with the total value of the refractive index change per mmol photoactive chromophore being much higher compared to the reference material used.

[0655] [Embodiment] (1) An ophthalmic device, or a precursor article for producing an ophthalmic device, comprising at least one polymeric compound of formula (I): [ka] During the ceremony, The divalent group [ka] is selected from the group of formula (B-1), formula (B-2), formula (B-3), formula (B-4) or formula (B-5), [ka] The asterisk * indicates the bond to the remainder of formula (I), Y1, Y2, Y3, and Y4 are each independently CR' or N, provided that only one of Y1, Y2, Y3, and Y4 is N, and the others are CR'; Y5 is O, S, or NR B and R B is independently selected in each occurrence from a linear or branched chain alkyl group having 1 to 10 carbon atoms, or a partially or fully fluorinated linear or branched chain alkyl group having 1 to 10 carbon atoms; X is O or S; Y0 is O or S; A1, A2, A3, and A4 are each independently N, CR″, or CY-R2-R1, provided that when m1 is 1, only one of A1, A2, A3, and A4 is N, and the others are CR″, provided that when m1 is 0, only one of A1, A2, A3, and A4 is N, and only one of A1, A2, A3, and A4 is CY-R2-R1, and the others are each independently CR″; or when m1 is 0, adjacent A1-A2, A2-A3, or A3-A4 are each independently -N(R2-R1)-C(=O)- or -C(=O)-N(R2-R1)-, and the remaining A3, A4, A1, and A2 are each independently CR''; Y's are, independently of one another, O, S, SO2 or a bond; m1 is 0 or 1, n1 is 4, n2 is 2, R' in each occurrence is independently selected from the group consisting of H, F, SF5, CN, SO2CF3, a straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkyl group having 1 to 20 carbon atoms, a non-halogenated, partially halogenated or fully halogenated cycloalkyl group having 3 to 6 carbon atoms, a straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkoxy group having 1 to 20 carbon atoms, and a straight or branched chain, non-halogenated, partially halogenated or fully halogenated thioalkyl group having 1 to 20 carbon atoms; R″ in each occurrence is independently selected from the group consisting of H, F, Cl, Br, CN, SO2CF3, straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkyl groups having from 1 to 20 carbon atoms, non-halogenated, partially halogenated or fully halogenated cycloalkyl groups having from 3 to 6 carbon atoms, straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkoxy groups having from 1 to 20 carbon atoms, and straight or branched chain, non-halogenated and partially halogenated or fully halogenated thioalkyl groups having from 1 to 20 carbon atoms; R1 is a trialkoxysilyl group or a dialkoxyalkylsilyl group in which the alkyl group and / or the alkoxy group are each independently linear or branched and have 1 to 6 carbon atoms, or a silyl group of formula (1), formula (2), or formula (3), or a polymerizable group of formula (4), [ka] where alkyl, in each occurrence, independently of one another, means a straight or branched chain alkyl group having 1 to 6 carbon atoms; 「*」 are, in each occurrence independently of each other, a linker -R2-, -R2-Y or [Y-R2-] m1 indicates a bond to During the ceremony, X 11 is selected from the group consisting of O, S, O-SO2, SO2-O, C(=O), OC(=O), C(=O)O, S(C=O), and (C=O)S; R5, R6, and R7, in each occurrence, are independently selected from the group consisting of H, F, linear or branched, non-fluorinated, partially fluorinated, or fully fluorinated alkyl groups having 1 to 20 carbon atoms, and aryl groups having 6 to 14 carbon atoms; c is 0 or 1; -R2- is -(C(R)2) o - or -(C(R)2) p -X8-(C(R)2) q -(X9) s -(C(R)2) r -(X10 ) t -(C(R)2) u - and R in each occurrence is independently selected from the group consisting of H, F, a linear or branched chain alkyl group having 1 to 4 carbon atoms, or a linear or branched chain partially or fully fluorinated alkyl group having 1 to 4 carbon atoms; o is selected from the group consisting of 0 to 20; X8, X9, X 10 is independently in each occurrence O, S, SO, or NR; s and t are 0 or 1; p, q are independently selected in each occurrence from the group consisting of 1 to 10; r, u are independently selected in each occurrence from the group consisting of 0 to 10, wherein -(C(R)2) p -X8-(C(R)2) q -(X9) s -(C(R)2) r -(X 10 ) t -(C(R)2) u The total number of atoms is at most 20, R0 in each occurrence is independently selected from the group consisting of linear or branched alkyl groups having 1 to 4 carbon atoms and linear or branched partially or fully fluorinated alkyl groups having 1 to 4 carbon atoms; R3 is H, F, Cl, Br, CN, or a linear or branched, non-halogenated, partially halogenated, or fully halogenated alkyl group having 1 to 20 carbon atoms; When m1 is 0, R4 is R'; When m1 is 1, R4 is R1; An ophthalmic device or a precursor article for manufacturing an ophthalmic device. (2) In the polymeric compound of formula (I), m1 is 0, and the compound is of formula (I'), [ka] In the formula, R1, -R2-, Y, R3, X, Y0, R', R'' and [ka] has the meaning as defined in embodiment 1, A1, A2, A3, and A4 are each independently N, CR″, or CY-R2-R1, provided that only one of A1, A2, A3, and A4 is N, only one of A1, A2, A3, and A4 is CY-R2-R1, and the others are each independently CR″; or, adjacent A1-A2, A2-A3, or A3-A4 are each independently -N(R2-R1)-C(=O)- or -C(=O)-N(R2-R1)-, and the remaining A3, A4, A1, and A2 are each independently CR''; R4 is H or R'; 10. An ophthalmic device according to claim 1, or a precursor article for producing an ophthalmic device. (3) In the polymeric compound of formula (I), m1 is 1, and the compound is of formula (I″), [ka] In the formula, R1, -R2-, Y, R3, X, Y0, R', R'' and [ka] has the meaning as defined in embodiment 1, A1, A2, A3, and A4 are each independently N or CR″, provided that only one of A1, A2, A3, and A4 is N, and the others are CR″; 10. An ophthalmic device according to claim 1, or a precursor article for producing an ophthalmic device. (4) Structural unit M based on formula (I), formula (I') or formula (I'') 0wherein R1 is polymerized in each occurrence and thus forms a regioregular, alternating, regiorandom, statistical, block, or random oligomeric or polymeric backbone or is part of a copolymeric backbone. (5) The polymerizable group R1 is represented by formula (1-p), formula (2-p), formula (3-p), or formula (4-p), [ka] The asterisks in formulas (1-p) to (4-p) 「*」 represents a bond to the adjacent repeating unit in the polymer chain or oligomer chain or to a terminal group, and the asterisk in formulas (1-p) to (4-p) 「**」 represents a bond to the remainder of formula (I), formula (I') or formula (I''); R5, R6, R7, X 11 5. An ophthalmic device, or a precursor article for producing an ophthalmic device, according to any one or more of embodiments 1 to 4, wherein c and c have the meanings as defined in embodiment 1.

[0656] (6) The structural unit M 0 But the formula (M 0 -I'-a), formula (M 0 -I'-b), formula (M 0 -I'-c), formula (M 0 -I'-d), formula (M 0 -I'-e), formula (M 0 -I'-f), formula (M 0 -I'-g), formula (M 0 -I'-h), formula (M 0 -I'-i) or formula (M 0 -I''), [ka] [ka] In the formula, R1, -R2-, X, Y0, Y, A1, A2, A3, A4, R3, R4, R5, R6, R7, X 11 , c and [ka] has the meaning as defined in embodiment 1, R4 is R', and an asterisk 「*」 6. The ophthalmic device of any one of claims 1 to 5, or a precursor article for making an ophthalmic device, wherein, in each occurrence, denotes a bond to the adjacent repeat unit in the polymeric or oligomeric chain or to a terminal group. (7) The at least one polymeric compound of formula (I), formula (I′) or formula (I″), or formula (M 0 -I'-a), formula (M 0 -I'-b), formula (M 0 -I'-c), formula (M 0 -I'-d), formula (M 0 -I'-e), formula (M 0 -I'-f), formula (M 0 -I'-g), formula (M 0 -I'-h), formula (M 0 -I'-i) or formula (M 0 -I'') structural unit M 0The side chain of styrene, ethoxyethyl methacrylate (EOEMA), methyl methacrylate (MMA), methyl acrylate, n-alkyl acrylate (n-alkyl group contains 2 to 20 carbon atoms), n-alkyl methacrylate (n-alkyl group contains 2 to 20 carbon atoms), i-alkyl acrylate (i-alkyl group contains 3 to 20 carbon atoms), i-alkyl methacrylate (i-alkyl group contains 3 to 20 carbon atoms), ethoxyethoxyethyl acrylate (EEEA), 2-hydroxyethyl methacrylate (HEMA), tetrahydrofuryl methacrylate (THFMA), glycidyl methacrylate (GMA), 16-hydroxyhexadecyl acrylate, 16-hydroxyhexadecyl methacrylate Acrylate, 18-hydroxyoctadecyl acrylate, 18-hydroxyoctadecyl methacrylate, 2-phenoxyethyl acrylate (EGPEA), heptafluorobutyl acrylate, heptafluorobutyl methacrylate, hexafluorobutyl acrylate, hexafluorobutyl methacrylate, hexafluoroisopropyl acrylate, hexafluoroisopropyl methacrylate, octafluoropentyl acrylate, octafluoropentyl methacrylate, pentafluoropropyl acrylate, pentafluoropropyl methacrylate, tetrafluoropropyl methacrylate, trifluoroethyl acrylate, trifluoroethyl methacrylate, bisphenol A diacrylate-1 7. The ophthalmic device, or precursor article for producing an ophthalmic device, of any one or more of embodiments 1-6, comprising at least one further polymerized monomer selected from the group consisting of EO / phenol (BPADA), 2-[3'-2'H-benzotriazol-2'-yl)-4'-hydroxyphenyl]ethyl methacrylate (BTPEM), or ethylene glycol dimethacrylate. 8. The ophthalmic device or precursor article for producing an ophthalmic device of claim 7, wherein the at least one additional polymerized monomer is selected from methyl methacrylate, 2-hydroxyethyl methacrylate, 2-phenoxyethyl acrylate, ethoxyethoxyethyl acrylate, 8-methylnonyl methacrylate, n-butyl methacrylate, 2-ethylhexyl methacrylate, or a mixture thereof. (9) -R2- is, independently in each occurrence, -(C(R)2) o - and R and o have the meanings given in embodiment 1. An ophthalmic device or a precursor article for producing an ophthalmic device according to any one of embodiments 1 to 8. (10) The ophthalmic device, or precursor article for producing an ophthalmic device, of any one of embodiments 1 to 9, wherein X is O and Y0 is O.

[0657] (11) The ophthalmic device, or precursor article for producing an ophthalmic device, of any one of embodiments 1 to 10, wherein polymerized R1, in each occurrence, is derived independently from an acrylic group or a methacrylic group. (12) A precursor article for producing an ophthalmic device according to any one of claims 1 to 11, wherein the precursor article is a blank that can be transformed into an ocular implant, preferably an intraocular lens. (13) A process for forming an ophthalmic device or a precursor article for manufacturing an ophthalmic device according to any one of embodiments 1 to 12, comprising: providing a composition comprising at least one compound of formula (I), (I'), or (I'') according to any one or more of embodiments 1 to 3, embodiment 9, and embodiment 10, and / or an oligomer or polymer according to any one or more of embodiments 4 to 8, and embodiment 11, with the proviso that at least one reactive group remaining for polymerization and optionally further monomers different from the compound of formula (I), (I'), or (I''), and / or a crosslinker, and / or an ultraviolet absorber, and / or a radical initiator; subsequently forming said ophthalmic device or precursor article from said composition. (14) A process for altering the optical properties of an ophthalmic device or a precursor article for producing an ophthalmic device according to any one of embodiments 1 to 12, comprising: Providing an ophthalmic device or precursor article according to claim 13; subsequently exposing the ophthalmic device or the precursor article to radiation having a wavelength of at least 200 nm and at most 1500 nm. (15) An ophthalmic device or a precursor article for producing an ophthalmic device obtained by the process of embodiment 14.

[0658] (16) An oligomer, polymer, or copolymer comprising at least one polymeric compound of formula (I) as defined in embodiment 1. (17) Styrene, ethoxyethyl methacrylate (EOEMA), methyl methacrylate (MMA), methyl acrylate, n-alkyl acrylate (n-alkyl group containing 2 to 20 carbon atoms), n-alkyl methacrylate (n-alkyl group containing 2 to 20 carbon atoms), i-alkyl acrylate (i-alkyl group containing 3 to 20 carbon atoms), i-alkyl methacrylate (i-alkyl group containing 3 to 20 carbon atoms), ethoxyethoxyethyl acrylate (EEEA), 2-hydroxyethyl methacrylate (HEMA), tetrahydrofuryl methacrylate (THFMA), glycidyl methacrylate (GMA), 16-hydroxyhexadecyl acrylate, 16-hydroxyhexadecyl methacrylate 17. The polymer of embodiment 16, comprising at least one further polymerized monomer in a side chain of the polymerized compound of Formula (I) selected from the group consisting of butyl acrylate, 18-hydroxyoctadecyl acrylate, 18-hydroxyoctadecyl methacrylate, 2-phenoxyethyl acrylate (EGPEA), heptafluorobutyl acrylate, heptafluorobutyl methacrylate, hexafluorobutyl acrylate, hexafluorobutyl methacrylate, hexafluoroisopropyl acrylate, hexafluoroisopropyl methacrylate, octafluoropentyl acrylate, octafluoropentyl methacrylate, pentafluoropropyl acrylate, pentafluoropropyl methacrylate, tetrafluoropropyl methacrylate, trifluoroethyl acrylate, trifluoroethyl methacrylate, bisphenol A diacrylate-1 EO / phenol (BPADA), 2-[3'-2'H-benzotriazol-2'-yl)-4'-hydroxyphenyl]ethyl methacrylate (BTPEM), or ethylene glycol dimethacrylate. (18) A polymerization composition comprising at least one compound of Formula (I), Formula (I'), or Formula (I'') according to any one or more of embodiments 1 to 3, embodiment 9, and embodiment 10, and / or an oligomer or polymer according to embodiment 16 or 17 having at least one reactive group remaining for polymerization, and / or a crosslinker, and / or an ultraviolet absorber, and / or a radical initiator, and optionally a further monomer different from the compound of Formula (I), Formula (I'), or Formula (I''). (19) A compound of formula (I), [ka] During the ceremony, The divalent group [ka] is selected from the group of formula (B-1), formula (B-2), formula (B-3), formula (B-4) or formula (B-5), [ka] The asterisk * indicates the bond to the remainder of formula (I), Y1, Y2, Y3, and Y4 are each independently CR' or N, provided that only one of Y1, Y2, Y3, and Y4 is N, and the others are CR'; Y5 is O, S, or NR B and R B is independently selected in each occurrence from a linear or branched chain alkyl group having 1 to 10 carbon atoms, or a partially or fully fluorinated linear or branched chain alkyl group having 1 to 10 carbon atoms; A1, A2, A3, and A4 are each independently N, CR″, or CY-R2-R1, provided that when m1 is 1, only one of A1, A2, and A3 is N, and the others and A4 are CR″, provided that when m1 is 0, only one of A1, A2, and A3 is N, and only one of A1, A2, A3, and A4 is CY-R2-R1, and the others are each independently CR″; or, when m1 is 0, adjacent A1-A2, A2-A3, or A3-A4 are each independently -N(R2-R1)-C(=O)- or -C(=O)-N(R2-R1)-, and the remaining A3, A4, A1, and A2 are each independently CR''; Y's are, independently of one another, O, S, SO2 or a bond; m1 is 0 or 1, n1 is 4, n2 is 2, R' in each occurrence is independently selected from the group consisting of H, F, SF5, CN, SO2CF3, a straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkyl group having 1 to 20 carbon atoms, a non-halogenated, partially halogenated or fully halogenated cycloalkyl group having 3 to 6 carbon atoms, a straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkoxy group having 1 to 20 carbon atoms, and a straight or branched chain, non-halogenated, partially halogenated or fully halogenated thioalkyl group having 1 to 20 carbon atoms; R″ in each occurrence is independently selected from the group consisting of H, F, Cl, Br, CN, SO2CF3, straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkyl groups having 1 to 20 carbon atoms, non-halogenated, partially halogenated or fully halogenated cycloalkyl groups having 3 to 6 carbon atoms, straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkoxy groups having 1 to 20 carbon atoms, and straight or branched chain, non-halogenated and partially halogenated or fully halogenated thioalkyl groups having 1 to 20 carbon atoms; R1 is a trialkoxysilyl group or a dialkoxyalkylsilyl group in which the alkyl group and / or the alkoxy group are each independently linear or branched and have 1 to 6 carbon atoms, or a silyl group of formula (1), formula (2), or formula (3), or a polymerizable group of formula (4), [ka] where alkyl, in each occurrence, independently of one another, means a straight or branched chain alkyl group having 1 to 6 carbon atoms; 「*」 are, in each occurrence independently of each other, a linker -R2-, -R2-Y or [Y-R2-] m1 indicates a bond to During the ceremony, X 11 is selected from the group consisting of O, S, O-SO2, SO2-O, C(=O), OC(=O), C(=O)O, S(C=O), and (C=O)S; R5, R6, and R7, in each occurrence, are independently selected from the group consisting of H, F, linear or branched, non-fluorinated, partially or fully fluorinated alkyl groups having 1 to 20 carbon atoms, and aryl groups having 6 to 14 carbon atoms; c is 0 or 1; -R2- is -(C(R)2) o - or -(C(R)2) p -X8-(C(R)2) q -(X9) s -(C(R)2) r -(X 10 ) t -(C(R)2) u - and R in each occurrence is independently selected from the group consisting of H, F, a linear or branched chain alkyl group having 1 to 4 carbon atoms, or a linear or branched chain partially or fully fluorinated alkyl group having 1 to 4 carbon atoms; o is 0 to 20, X8, X9, X 10 is independently in each occurrence O, S, SO, or NR; s and t are 0 or 1, p and q are independently selected in each occurrence from the group consisting of 1 to 10; r and u are independently selected in each occurrence from the group consisting of 0 to 10, wherein -(C(R)2) p -X8-(C(R)2) q -(X9) s -(C(R)2) r -(X 10 ) t -(C(R)2) u The total number of atoms is at most 20, R0 in each occurrence is independently selected from the group consisting of linear or branched alkyl groups having 1 to 4 carbon atoms, and linear or branched partially or fully fluorinated alkyl groups having 1 to 4 carbon atoms; R3 is H, F, Cl, Br, CN, or a linear or branched, non-halogenated, partially halogenated, or fully halogenated alkyl group having 1 to 20 carbon atoms; When m1 is 0, R4 is R'; when m1 is 1, R4 is R1; However, when m1 is 0, Y is O or S, and A2 is CY-R2-R1, The divalent group [ka] is at the 3-position and is selected from formula (B-3) and formula (B-4), Y4 in formula (B-3) is N, Y3 in formula (B-4) is N, and c is 1; However, when m1 is 1, A2 is CR″, and R″ is a linear or branched, non-halogenated, partially halogenated or fully halogenated alkoxy group having 1 to 20 carbon atoms, and a linear or branched, non-halogenated, partially halogenated or fully halogenated thioalkyl group having 1 to 20 carbon atoms, The divalent group [ka] is at the 3-position and is selected from formula (B-3), wherein Y2 in formula (B-3) is CR', R' is H, Y4 in formula (B-3) is N, Y is a bond, O or S, and c is 1; However, when m1 is 1, Y is a bond, c is 0, and R3 is Cl, The divalent group [ka] is in third place, o is 5-20, However, when m1 is 0, Y is a bond or O, c is 0, and R3 is Cl, The divalent group [ka] is in third place, o is 7-20, However, when m1 is 0, X is O, Y0 is O, and Y is a bond, c is 1 and X 11 are O, S, O-SO2, SO2-O, OC(=O), C(=O)O, S(C=O) and (C=O)S, However, when m1 is 1, X is O, and Y0 is O, o is 5 to 20; However, when m1 is 1, c is 0, and Y is a bond or O, The divalent group [ka] is in third place, o is 11-20, However, when m1 is 1, A1 or A3 is N, Y is a bond, and c is 0, The divalent group [ka] is in third place, o is 7-20, However, when m1 is 0, X is O, Y0 is O, Y is O or S, c is 0, A2 is CY-R2-R1, A3 is Br, and A1 is N, The divalent group [ka] is at the 4-position and is selected from formula (B-1), formula (B-3), and formula (B-4), and o is 2 to 20; compound.

Claims

1. 1. An ophthalmic device, or a precursor article for producing an ophthalmic device, comprising an oligomer, polymer, or copolymer comprising constitutional units based on at least one compound of formula (I), 【Chemistry 1】 During the ceremony, The divalent group 【Chemistry 2】 is selected from the group consisting of formula (B-1), formula (B-2), formula (B-3), formula (B-4) and formula (B-5), 【Transformation 3】 The asterisk ＊ indicates the bond to the remainder of formula (I), Y １ , Y ２ , Y ３ , Y ４ are each independently CR′ or N, provided that Y １ , Y ２ , Y ３ , and Y ４ is N, and the others are CR′; Y ５ is O, S, or NR Ｂ and R Ｂ is independently selected in each occurrence from a linear or branched chain alkyl group having 1 to 10 carbon atoms, or a partially or fully fluorinated linear or branched chain alkyl group having 1 to 10 carbon atoms; X is O or S; Y ０ is O or S, A １ , A ２ , A ３ , A ４ are each independently N, CR″ or CYR ２ -R １ provided that when m1 is 1, A １ , A ２ , A ３ and A ４ Only one of them is N, and the others are CR'', provided that when m1 is 0, A １ , A ２ , A ３ and A ４ Only one of the following is N, and A １ , A ２ , A ３ and A ４ Only one of the following is C-Y-R ２ -R １ and the others are each independently CR''; or When m1 is 0, the adjacent A １ -A ２ , A ２ -A ３ or A ３ -A ４ are each independently -N(R ２ -R １ )-C(=O)- or -C(=O)-N(R ２ -R １ )-, and the remainder A ３ , A ４ , A １ , and A ２ are each independently CR″; Y's are independently O, S, SO ２ , or a bond, m1 is 0 or 1; n1 is 4, n2 is 2, R' is independently in each occurrence H, F, SF ５ , C.N., S.O. ２ CF ３ a linear or branched, non-halogenated, partially halogenated or fully halogenated alkyl group having 1 to 20 carbon atoms, a non-halogenated, partially halogenated or fully halogenated cycloalkyl group having 3 to 6 carbon atoms, a linear or branched, non-halogenated, partially halogenated or fully halogenated alkoxy group having 1 to 20 carbon atoms, and a linear or branched, non-halogenated, partially halogenated or fully halogenated thioalkyl group having 1 to 20 carbon atoms; R″ is independently in each occurrence H, F, Cl, Br, CN, SO ２ CF ３ , a straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkyl group having 1 to 20 carbon atoms, a non-halogenated, partially halogenated or fully halogenated cycloalkyl group having 3 to 6 carbon atoms, a straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkoxy group having 1 to 20 carbon atoms, and a straight or branched chain, non-halogenated and partially halogenated or fully halogenated thioalkyl group having 1 to 20 carbon atoms; R １ is a polymerizable group of formula (4), 【Chemistry 4】 where the asterisk 「＊」 are, in each occurrence independently of each other, a linker -R ２ -, -R ２ -Y or [Y-R ２ -] ｍ１ indicates the bond to During the ceremony, X １１ is O, S, O-SO ２ , S.O. ２ is selected from the group consisting of —O, C(═O), OC(═O), C(═O)O, S(C═O), and (C═O)S; R ５ , R ６ , R ７ are each independently selected from the group consisting of H, F, linear or branched, non-fluorinated, partially fluorinated or fully fluorinated alkyl groups having 1 to 20 carbon atoms, and aryl groups having 6 to 14 carbon atoms; c is 0 or 1; -R ２ - is - (C (R) ２ ) ｏ - or - (C(R) ２ ) ｐ -X ８ -(C(R) ２ ) ｑ -(X ９ ) ｓ -(C(R) ２ ) ｒ -(X １０ ) ｔ -(C(R) ２ ) ｕ - and R in each occurrence is independently selected from the group consisting of H, F, a linear or branched chain alkyl group having 1 to 4 carbon atoms, or a linear or branched chain partially or fully fluorinated alkyl group having 1 to 4 carbon atoms; o is selected from the group consisting of 0 to 20; X ８ , X ９ , X １０ is independently O, S, SO in each occurrence ２ , or NR ０ and s and t are 0 or 1; p, q are independently in each occurrence selected from the group consisting of 1 to 10; r, u are independently selected in each occurrence from the group consisting of 0 to 10, wherein -(C(R) ２ ) ｐ -X ８ -(C(R) ２ ) ｑ -(X ９ ) ｓ -(C(R) ２ ) ｒ -(X １０ ) ｔ -(C(R) ２ ) ｕ The total number of atoms is up to 20, R ０ is independently in each occurrence selected from the group consisting of linear or branched chain alkyl groups having 1 to 4 carbon atoms and linear or branched chain partially or fully fluorinated alkyl groups having 1 to 4 carbon atoms; R ３ is H, F, Cl, Br, CN, or a linear or branched, non-halogenated, partially halogenated, or fully halogenated alkyl group having 1 to 20 carbon atoms; When m1 is 0, R ４ is R', When m1 is 1, R ４ is R １ That is, An ophthalmic device or a precursor article for manufacturing an ophthalmic device.

2. In the compound of formula (I), m1 is 0 and the compound is of formula (I'), 【Transformation 5】 In the formula, R １ , -R ２ -, Y, R ３ , X, Y ０ , R', R'' and 【Transformation 6】 has the meaning as defined in claim 1, A １ , A ２ , A ３ , A ４ are each independently N, CR″ or CYR ２ -R １ However, A １ , A ２ , A ３ and A ４ Only one of the following is N, and A １ , A ２ , A ３ and A ４ Only one of the following is C-Y-R ２ -R １ and the others are each independently CR''; or, Adjacent A １ -A ２ , A ２ -A ３ or A ３ -A ４ are each independently -N(R ２ -R １ )-C(=O)- or -C(=O)-N(R ２ -R １ )-, and the remainder A ３ , A ４ , A １ , and A ２ are each independently CR″; R ４ is H or R'; 10. An ophthalmic device according to claim 1, or a precursor article for producing an ophthalmic device.

3. In the compound of formula (I), m1 is 1 and the compound is of formula (I″), 【Transformation 7】 In the formula, R １ , -R ２ -, Y, R ３ , X, Y ０ , R', R'' and 【Transformation 8】 has the meaning as defined in claim 1, A １ , A ２ , A ３ , A ４ are each independently N or CR″, provided that A １ , A ２ , A ３ and A ４ Only one of the following is N, and the others are CR″; 10. An ophthalmic device according to claim 1, or a precursor article for producing an ophthalmic device.

4. A structural unit M based on formula (I), formula (I') or formula (I'') ０ and wherein R １ is polymerized in each occurrence, and therefore R １ 4. An ophthalmic device, or a precursor article for producing an ophthalmic device, according to any one or more of claims 1 to 3, wherein:

5. the oligomer, polymer, or copolymer comprises a moiety of formula (4-p): 【Chemistry 9】 The asterisk in formula (4-p) 「＊」 represents a bond to the adjacent repeating unit in the polymer chain or oligomer chain or to a terminal group, and the asterisk in formula (4-p) 「＊＊」 represents a bond to the remainder of formula (I), formula (I′) or formula (I″), and R ５ , R ６ , R ７ , X １１ An ophthalmic device or a precursor article for producing an ophthalmic device according to any one or more of claims 1 to 4, wherein and c have the meaning as defined in claim 1.

6. The structural unit M ０ is expressed as follows: ０ -I'-a), formula (M ０ -I'-b), formula (M ０ -I'-c), formula (M ０ -I'-d), formula (M ０ -I'-e), formula (M ０ -I'-f), formula (M ０ -I'-g), formula (M ０ -I'-h), formula (M ０ -I'-i) or formula (M ０ -I″), 【Chemistry 10】 【Chemistry 11】 where, R １ , -R ２ , X, Y ０ , Y, A １ , A ２ , A ３ , A ４ , R ３ , R ４ , R ５ , R ６ , R ７ , X １１ , c and 【Chemistry 12】 has the meaning as defined in claim 1, R ４ is R' and an asterisk 「＊」 5. The ophthalmic device or precursor article for producing an ophthalmic device of claim 4, wherein, in each occurrence, represents a bond to the adjacent repeat unit in the polymeric or oligomeric chain or to a terminal group.

7. The oligomer, polymer, or copolymer, comprising a building block based on said at least one compound of formula (I), formula (I′), or formula (I″), or a building block based on said at least one compound of formula (M ０ -I'-a), formula (M ０ -I'-b), formula (M ０ -I'-c), formula (M ０ -I'-d), formula (M ０ -I'-e), formula (M ０ -I'-f), formula (M ０ -I'-g), formula (M ０ -I'-h), formula (M ０ -I'-i) or formula (M ０ -I″) structural unit M ０ Along with styrene, ethoxyethyl methacrylate (EOEMA), methyl methacrylate (MMA), methyl acrylate, n-alkyl acrylate (n-alkyl group containing 2 to 20 carbon atoms), n-alkyl methacrylate (n-alkyl group containing 2 to 20 carbon atoms), i-alkyl acrylate (i-alkyl group containing 3 to 20 carbon atoms), i-alkyl methacrylate (i-alkyl group containing 3 to 20 carbon atoms), ethoxyethoxyethyl acrylate (EEEA), 2-hydroxyethyl methacrylate (HEMA), tetrahydrofuryl methacrylate (THFMA), glycidyl methacrylate (GMA), 16-hydroxyhexadecyl acrylate, 16-hydroxyhexadecyl methacrylate Acrylate, 18-hydroxyoctadecyl acrylate, 18-hydroxyoctadecyl methacrylate, 2-phenoxyethyl acrylate (EGPEA), heptafluorobutyl acrylate, heptafluorobutyl methacrylate, hexafluorobutyl acrylate, hexafluorobutyl methacrylate, hexafluoroisopropyl acrylate, hexafluoroisopropyl methacrylate, octafluoropentyl acrylate, octafluoropentyl methacrylate, pentafluoropropyl acrylate, pentafluoropropyl methacrylate, tetrafluoropropyl methacrylate, trifluoroethyl acrylate, trifluoroethyl methacrylate, bisphenol A diacrylate-1 7. An ophthalmic device, or a precursor article for producing an ophthalmic device, according to any one or more of claims 1 to 6, comprising building blocks based on at least one further monomer selected from the group consisting of EO / phenol (BPADA), 2-[3'-2'H-benzotriazol-2'-yl)-4'-hydroxyphenyl]ethyl methacrylate (BTPEM) or ethylene glycol dimethacrylate.

8. 8. The ophthalmic device, or precursor article for producing an ophthalmic device, of claim 7, wherein the at least one additional monomer is selected from methyl methacrylate, 2-hydroxyethyl methacrylate, 2-phenoxyethyl acrylate, ethoxyethoxyethyl acrylate, 8-methylnonyl methacrylate, n-butyl methacrylate, 2-ethylhexyl methacrylate, or mixtures thereof.

9. -R ２ -, independently in each occurrence, -(C(R) ２ ) ｏ - and R and o have the meanings indicated in claim 1, or a precursor article for producing an ophthalmic device according to any one or more of claims 1 to 8.

10. X is O and Y ０ An ophthalmic device or precursor article for producing an ophthalmic device according to any one or more of claims 1 to 9, wherein:

11. Polymerized R １ 11. An ophthalmic device, or precursor article for making an ophthalmic device, according to any one or more of claims 1 to 10, wherein, in each occurrence, is independently derived from an acrylic or methacrylic group.

12. A precursor article for manufacturing an ophthalmic device according to any one or more of claims 1 to 11, wherein said precursor article is a blank that can be transformed into an ocular implant, preferably an intraocular lens.

13. A process for forming an ophthalmic device or a precursor article for manufacturing an ophthalmic device according to any one or more of claims 1 to 12, comprising: providing a composition comprising at least one compound of formula (I), (I') or (I'') according to any one or more of claims 1 to 3 and 9 to 10, and / or an oligomer or polymer according to any one or more of claims 4 to 8 and 11, with the proviso that at least one reactive group remaining for polymerization and optionally a further monomer different from the compound of formula (I), (I') or (I''), and / or a crosslinker, and / or a UV absorber, and / or a radical initiator, subsequently forming said ophthalmic device or precursor article from said composition.

14. A process for modifying the optical properties of an ophthalmic device or a precursor article for producing an ophthalmic device according to any one or more of claims 1 to 12, comprising: Providing an ophthalmic device or precursor article according to claim 13; subsequently exposing the ophthalmic device or the precursor article to radiation having a wavelength of at least 200 nm and at most 1500 nm.

15. 10. An oligomer, polymer or copolymer comprising constitutional units based on at least one compound of formula (I) as defined in claim 1.

16. Styrene, ethoxyethyl methacrylate (EOEMA), methyl methacrylate (MMA), methyl acrylate, n-alkyl acrylate (n-alkyl group containing 2 to 20 carbon atoms), n-alkyl methacrylate (n-alkyl group containing 2 to 20 carbon atoms), i-alkyl acrylate (i-alkyl group containing 3 to 20 carbon atoms), i-alkyl methacrylate (i-alkyl group containing 3 to 20 carbon atoms), ethoxyethoxyethyl acrylate (EEEA), 2-hydroxyethyl methacrylate (HEMA), tetrahydrofuryl methacrylate (THFMA), glycidyl methacrylate (GMA), 16-hydroxyhexadecyl acrylate, 16-hydroxyhexadecyl methacrylate acrylate, 18-hydroxyoctadecyl acrylate, 18-hydroxyoctadecyl methacrylate, 2-phenoxyethyl acrylate (EGPEA), heptafluorobutyl acrylate, heptafluorobutyl methacrylate, hexafluorobutyl acrylate, hexafluorobutyl methacrylate, hexafluoroisopropyl acrylate, hexafluoroisopropyl methacrylate, octafluoropentyl acrylate, octafluoropentyl methacrylate, pentafluoropropyl acrylate, pentafluoropropyl methacrylate, tetrafluoropropyl methacrylate, trifluoroethyl acrylate, trifluoroethyl methacrylate, bisphenol A diacrylate-1 16. The polymer of claim 15, comprising, together with constitutional units based on the compound of formula (I), constitutional units based on at least one further monomer selected from the group consisting of EO / phenol (BPADA), 2-[3'-2'H-benzotriazol-2'-yl)-4'-hydroxyphenyl]ethyl methacrylate (BTPEM) or ethylene glycol dimethacrylate.

17. A composition for polymerization comprising at least one compound of formula (I), formula (I') or formula (I") according to any one or more of claims 1 to 3 and 9 to 10, and / or an oligomer or polymer according to claim 15 or 16 having at least one reactive group remaining for polymerization, and / or a crosslinking agent, and / or an ultraviolet absorber, and / or a radical initiator, and optionally a further monomer different from the compound of formula (I), formula (I') or formula (I")

18. A compound of formula (I) 【Chemistry 13】 During the ceremony, The divalent group 【Chemistry 14】 is selected from the group consisting of formula (B-1), formula (B-2), formula (B-3), formula (B-4) and formula (B-5), 【Chemistry 15】 The asterisk ＊ indicates the bond to the remainder of formula (I), Y １ , Y ２ , Y ３ , Y ４ are each independently CR′ or N, provided that Y １ , Y ２ , Y ３ , and Y ４ is N, and the others are CR′; Y ５ is O, S, or NR Ｂ and R Ｂ is independently selected in each occurrence from a linear or branched chain alkyl group having 1 to 10 carbon atoms, or a partially or fully fluorinated linear or branched chain alkyl group having 1 to 10 carbon atoms; X is O or S; Y 0 is O or S; A １ , A ２ , A ３ , A ４ are each independently N, CR″ or CYR ２ -R １ provided that when m1 is 1, A １ , A ２ and A ３ Only one of these is N, and the others are A. ４ and CR″, provided that when m1 is 0, A １ , A ２ and A ３ is N, and A １ , A ２ , A ３ and A ４ Only one of the following is C-Y-R ２ -R １ and the others are each independently CR''; or, When m1 is 0, the adjacent A １ -A ２ , A ２ -A ３ or A ３ -A ４ are each independently -N(R ２ -R １ )-C(=O)- or -C(=O)-N(R ２ -R １ )-, and the remainder A ３ , A ４ , A １ , and A ２ are each independently CR″; Y's are independently O, S, SO ２ , or a bond, m1 is 0 or 1; n1 is 4, n2 is 2, R' is independently in each occurrence H, F, SF ５ , C.N., S.O. ２ CF ３ a linear or branched, non-halogenated, partially halogenated or fully halogenated alkyl group having 1 to 20 carbon atoms, a non-halogenated, partially halogenated or fully halogenated cycloalkyl group having 3 to 6 carbon atoms, a linear or branched, non-halogenated, partially halogenated or fully halogenated alkoxy group having 1 to 20 carbon atoms, and a linear or branched, non-halogenated, partially halogenated or fully halogenated thioalkyl group having 1 to 20 carbon atoms; R″ is independently in each occurrence H, F, Cl, Br, CN, SO ２ CF ３ , a straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkyl group having 1 to 20 carbon atoms, a non-halogenated, partially halogenated or fully halogenated cycloalkyl group having 3 to 6 carbon atoms, a straight or branched chain, non-halogenated, partially halogenated or fully halogenated alkoxy group having 1 to 20 carbon atoms, and a straight or branched chain, non-halogenated and partially halogenated or fully halogenated thioalkyl group having 1 to 20 carbon atoms; R １ is a trialkoxysilyl group or dialkoxyalkylsilyl group in which the alkyl group and / or alkoxy group are each independently linear or branched and have 1 to 6 carbon atoms, or a silyl group of formula (1), formula (2), or formula (3), or a polymerizable group of formula (4), 【Chemistry 16】 where alkyl in each occurrence independently means a straight or branched chain alkyl group having 1 to 6 carbon atoms; 「＊」 are, in each occurrence independently of each other, a linker -R ２ -, -R ２ -Y or [Y-R ２ -] ｍ１ indicates the bond to During the ceremony, X １１ is O, S, O-SO ２ , S.O. ２ is selected from the group consisting of —O, C(═O), OC(═O), C(═O)O, S(C═O), and (C═O)S; R ５ , R ６ , R ７ are each independently selected from the group consisting of H, F, straight or branched chain, non-fluorinated, partially or fully fluorinated alkyl groups having 1 to 20 carbon atoms, and aryl groups having 6 to 14 carbon atoms; c is 0 or 1; -R ２ - is - (C (R) ２ ) ｏ - or - (C(R) ２ ) ｐ -X ８ -(C(R) ２ ) ｑ -(X ９ ) ｓ -(C(R) ２ ) ｒ -(X １０ ) ｔ -(C(R) ２ ) ｕ - and R in each occurrence is independently selected from the group consisting of H, F, a linear or branched chain alkyl group having 1 to 4 carbon atoms, or a linear or branched chain partially or fully fluorinated alkyl group having 1 to 4 carbon atoms; o is 0 to 20; X ８ , X ９ , X １０ is independently O, S, SO in each occurrence ２ , or NR ０ and s and t are 0 or 1; p, q in each occurrence are independently selected from the group consisting of 1 to 10; r, u are independently selected in each occurrence from the group consisting of 0 to 10, wherein -(C(R) ２ ) ｐ -X ８ -(C(R) ２ ) ｑ -(X ９ ) ｓ -(C(R) ２ ) ｒ -(X １０ ) ｔ -(C(R) ２ ) ｕ The total number of atoms is up to 20, R ０ is independently in each occurrence selected from the group consisting of linear or branched chain alkyl groups having 1 to 4 carbon atoms, and linear or branched chain partially or fully fluorinated alkyl groups having 1 to 4 carbon atoms; R ３ is H, F, Cl, Br, CN, or a linear or branched, non-halogenated, partially halogenated, or fully halogenated alkyl group having 1 to 20 carbon atoms; When m1 is 0, R ４ is R', When m1 is 1, R ４ is R １ and provided that m1 is 0, Y is O or S, and A ２ is C-Y-R ２ -R １ If The divalent group 【Chemistry 17】 is at the 3-position and is selected from formula (B-3) and formula (B-4), and Y in formula (B-3) ４ is N, and Y in formula (B-4) ３ is N, c is 1, However, m1 is 1, and A ２ is CR″, where R″ is a linear or branched, non-halogenated, partially halogenated or fully halogenated alkoxy group having 1 to 20 carbon atoms, and a linear or branched, non-halogenated and partially halogenated or fully halogenated thioalkyl group having 1 to 20 carbon atoms; The divalent group [Chemistry 18] is at the 3-position and is selected from formula (B-3), and Y ２ is CR', R' is H, and Y in formula (B-3) ４ is N, Y is a bond, O or S, c is 1, provided that m1 is 1, Y is a bond, c is 0, and R ３ When is Cl, The divalent group 【Chemistry 19】 is in the third position, o is 5 to 20, provided that m1 is 0, Y is a bond or O, c is 0, and R ３ When is Cl, The divalent group 【Chemistry 20】 is in the third position, o is 7 to 20, provided that m1 is 0, X is O, and Y ０ is O and Y is a bond, then c is 1, and X １１ is O, S, O-SO ２ , S.O. ２ -O, OC(=O), C(=O)O, S(C=O) and (C=O)S; provided that m1 is 1, X is O, and Y ０ When is O, o is 5 to 20; However, when m1 is 1, c is 0, and Y is a bond or O, The divalent group 【Chemistry 21】 is in the third position, o is 11 to 20, However, m1 is 1, and A １ or A ３ is N, Y is a bond, and c is 0, The divalent group 【Chemistry 22】 is in the third position, o is 7 to 20, provided that m1 is 0, X is O, and Y ０ is O, Y is O or S, c is 0, and A ２ is C-Y-R ２ -R １ and A ３ is Br, and A １ If is N, then The divalent group 【Chemistry 23】 is in the 4-position and is selected from formula (B-1), formula (B-3), and formula (B-4), and o is 2 to 20; compound.

Images