composition

Abstract

The present invention encompasses composition comprising (a) monomer(s), (b) catalyst, (c) photoactive compound and (d) silicone-based surfactant. The composition of the present invention may be used to make display device application, for example a liquid crystal, quantum dot, μLED and OLED display fabricated on a substrate controlled by semiconductors.

Description

[0001] Foreignfiling text P24-225

[0002] - 1 -

[0003] Composition

[0004] Field of the invention

[0005] The present application relates to a composition comprising (a)

[0006] 5 polycycloolefin monomer(s), (b) catalyst, (c) photoactive compound and (d) silicone-based surfactant; using thereof; manufacturing a film; and manufacturing an electronic device.

[0007] Background Art

[0008] Electronic devices, and particularly organic electronic devices, have become thinner and thinner over the years, thereby now allowing for devices that can be rolled or bent. This development has led to the development and recent market introduction of, for example, smartphones with foldable displays based on organic light emitting device technology.

[0009] 15

[0010] US11535702B2 describes a composition that is capable of making a substantially transparent film or a three dimensional object.

[0011] US7875686B2 describes an encapsulant formulation that can be used as 20 die attach adhesives, underfill materials, prepreg binders, encapsulants, protective layers, and other related applications.

[0012] Citation list

[0013] Patent Literature

[0014] 1. US11535702B2

[0015] 2. US7875686B2

[0016] Summary of the invention

[0017] However, such devices are sensitive to environmental influences,

[0018] 30 especially to oxygen and moisture. If not protected, their performance will degrade over time, in some instances even rather quickly. Foreignfiling text P24-225

[0019] -2 -

[0020] Additionally, the mechanical stresses induced by folding and bending may also lead to fractures in any of the device layers directly in or in proximity to the fold or bend. The mechanical properties of the material as a thin film need to be suitable to withstand this stress.

[0021] 5

[0022] Furthermore the integration of a capacitive touch panel with a flexible or foldable OLED display may suffer from low touch sensitivity due to electronic interference of the two components. The layers in between should feature as low a dielectric constant as possible. There are many solvent-free inks (also for thin film encapsulation) on the market, based on epoxy- or acrylate-bearing monomers. The potential disadvantage of such materials systems is relatively high permittivity (Dk>3).

[0023] Low k (low dielectric constant) TFE (thin film encapsulation) compositions 15 suffer from wetting properties. Due to their non-polar components, low k TFE compositions do not show strong adhesion to surfaces. They easily show dewetting after printing which can be observed by the printed pattern / shape which changes to a shape of minimum surface and interface.

[0024] 20 Therefore, it is desired to provide higher transparency of the composition and / or an obtained film at visible light wavelength; lower haze value of an obtained film; lower dielectric constant of a composition and an obtained film, e.g. dielectric constant lower than 3 and low-loss lesser than 0.001 at high frequencies such as for example greater than 50 GHz; lower permittivity of a composition and an obtained film, improved touch sensitivity of an obtained film, high refractive index, good mechanical properties of an obtained film against mechanical stress such as folding and bending; good curing ratio of a composition; good thermal properties; lower surface tension of the composition; improved wetting properties of the 30 composition and / or an obtained film; balanced adhesion of the obtained film so that the film stays in the shape that it is printed. Foreignfiling text P24-225

[0025] - 3 -

[0026] The inventors aimed to solve one or more of the above-mentioned problems.

[0027] Then, the present inventors have surprisingly found that one or more of the 5 above-described technical problems can be solved by the features as defined in the claims.

[0028] Namely, it was found a novel composition comprising at least, essentially consisting of or consisting of:

[0029] a) one or more chemical compound of formula (I):

[0030]

[0031] 15

[0032]

[0033] wherein

[0034] m is an integer 0, 1 or 2;

[0035] Ri, R2, R3 and R4 are the same or different and each independently selected from the group consisting of hydrogen, halogen, methyl, ethyl, 20 linear or branched (C3-Cie)alkyl, perfluoro(Ci-Ci2)alkyl,

[0036] hydroxy(Ci-Cie)alkyl, (C3-Ci2)cycloalkyl, (C6-Ci2)bicycloalkyl,

[0037] (C7-Ci4)tricycloalkyl, (Ce-Cio)aryl, (C6-Cio)aryl(Ci-Ce)alkyl, perfluoro(Ce-Cio)aryl, perfluoro(C6-Cio)aryl(Ci-C6)alkyl, tri(Ci-Ce)alkoxysilyl and a group of formula (A):

[0038] -Z1-Aryl (A)

[0039] wherein

[0040] Z1is a bond or a group selected from the group consisting of:

[0041] 30 (CR5R6)a, O(CR5R6)a, (CR5R6)aO, (CR5R6)a-O-(CR5R6)b,

[0042] (CR5R6)a-O-(SiR5R6)b, (CR5R6)a-(CO)O-(CR5R6)b,

[0043] (CR5R6)a-O(CO)-(CR5R6)b, (CR5R6)a-(CO)-(CR5R6)b, where a and b are Foreignfiling text P24-225

[0044] integers which may be the same or different and each independently is 1 to 12;

[0045] Rs and Re are the same or different and each independently selected from the group consisting of hydrogen, methyl, ethyl, linear or branched (C3- 5 Ce)alkyl, hydroxy, methoxy, ethoxy, linear or branched (C3-Ce)alkyloxy, acetoxy, (C2-Ce)acyl, hydroxymethyl, hydroxyethyl, linear or branched hydroxy(C3-Ce)alkyl, phenyl and phenoxy;

[0046] Aryl is phenyl or phenyl substituted with one or more of groups selected from the group consisting of methyl, ethyl, linear or branched (C3-Ce)alkyl, 10 hydroxy, methoxy, ethoxy, linear or branched (C3-Ce)alkyloxy, acetoxy, (C2- Ce)acyl, hydroxymethyl, hydroxyethyl, linear or branched hydroxy(C3- Ce)alkyl, phenyl and phenoxy;

[0047] b) a catalyst, preferably a transition metal containing catalyst compound;

[0048] (c) a photoactive compound represented by formula (III):

[0049] 20

[0050]

[0051] wherein

[0052] Y is halogen or hydrogen; and

[0053] R30 and R31 are the same or different and independently of each other selected from the group consisting of hydrogen, methyl, ethyl, linear or branched (C3-Ci2)alkyl, (C3-Ci2)cycloalkyl, (C6-Ci2)bicycloalkyl,

[0054] (C7-Ci4)tricycloalkyl, (Ce-Cio)aryl, (C6-Cio)aryl(Ci-C3)alkyl, (Ci-Ci2)alkoxy, (C3-Ci2)cycloalkoxy, (C6-Ci2)bicycloalkoxy, (C7-Ci4)tricycloalkoxy,

[0055] (C6-Cio)aryloxy(Ci-C3)alkyl and (Ce-Cio)aryloxy; and

[0056] 30

[0057] (d) a silicone-based surfactant. Foreignfiling text P24-225

[0058] - 5 -

[0059] The present invention may relate to use of the composition of the present invention for fabricating a film, preferably for fabricating an optical film for an electronic device.

[0060] 5 Also, the present application provides a method of manufacturing a film comprising steps of; (1) preparing a base member; (2) applying the composition according to this invention above the base member; and (3) polymerizing the (a) monomers in the composition.

[0061] As another embodiment, the present application provides a film obtained or obtainable by the method according to this invention.

[0062] As another embodiment, the present application provides an electronic device comprising the film of this invention.

[0063] 15

[0064] Technical effects of the invention

[0065] The present invention may provide one or more of following effects: providing higher transparency of the composition and / or an obtained film at visible light wavelength; lower haze value of an obtained film; lower

[0066] 20 dielectric constant of a composition and an obtained film, e.g. dielectric constant lower than 3 and low-loss lesser than 0.001 at high frequencies such as for example greater than 50 GHz; lower permittivity of a composition and an obtained film, improved touch sensitivity of an obtained film, high refractive index, good mechanical properties of an obtained film against mechanical stress such as folding and bending; good curing ratio of a composition; good thermal properties; lower surface tension of the composition; improved wetting properties of the composition and / or an obtained film; balanced adhesion of the obtained film so that the film stays in the shape that it is printed.

[0067] 30

[0068] Preferred embodiments of the present invention are described hereinafter and in the dependent claims. Foreignfiling text P24-225

[0069] - 6 -

[0070] Definition of the terms

[0071] The terms as used herein have the following meanings:

[0072] As used herein, the articles “a,” “an,” and “the” include plural referents 5 unless otherwise expressly and unequivocally limited to one referent.

[0073] Since all numbers, values and / or expressions referring to quantities of ingredients, reaction conditions, etc., used herein and in the claims appended hereto, are subject to the various uncertainties of measurement encountered in obtaining such values, unless otherwise indicated, all are to be understood as modified in all instances by the term “about.”

[0074] Where a numerical range is disclosed herein such range is continuous, 15 inclusive of both the minimum and maximum values of the range as well as every value between such minimum and maximum values. Still further, where a range refers to integers, every integer between the minimum and maximum values of such range is included. In addition, where multiple ranges are provided to describe a feature or

[0075] 20 characteristic, such ranges can be combined. That is to say that, unless otherwise indicated, all ranges disclosed herein are to be understood to encompass any and all sub-ranges subsumed therein.

[0076] For example, a stated range of from “1 to 10” should be considered to include any and all sub-ranges between the minimum value of 1 and the maximum value of 10. Exemplary sub-ranges of the range 1 to 10 include, but are not limited to, 1 to 6.1, 3.5 to 7.8, and 5.5 to 10, etc.

[0077] The descriptions such as “Cx-y”, “Cx-Cy” and “Cx” mean the number of 30 carbons in a molecule or substituent. For example, C1-6 alkyl means an alkyl chain having 1 or more and 6 or less carbons (methyl, ethyl, propyl, butyl, pentyl, hexyl etc.). Foreignfiling text P24-225

[0078] - 7 -

[0079] As used herein, the expression “alkyl” means a saturated, straight-chain or branched-chain hydrocarbon substituent having the specified number of carbon atoms. Particular alkyl groups are methyl, ethyl, n-propyl, isopropyl, 5 n-butyl, iso-butyl, tert-butyl, and so on. Derived expressions such as “alkoxy”, “thioalkyl”, “alkoxyalkyl”, “hydroxyalkyl”, “alkylcarbonyl”, “alkoxycarbonylalkyl”, “alkoxycarbonyl”, “diphenylalkyl”, “phenylalkyl”, “phenylcarboxyalkyl” and “phenoxyalkyl” are to be construed accordingly.

[0080] As used herein, the expression “cycloalkyl” includes all of the known cyclic groups. Representative examples of “cycloalkyl” includes without any limitation cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and the like. Derived expressions such as “cycloalkoxy”, “cycloalkylalkyl”, “cycloalkylaryl”, “cycloalkylcarbonyl” are to be construed 15 accordingly.

[0081] As used herein the expression “acyl” shall have the same meaning as “alkanoyl”, which can also be represented structurally as “R-CO-,” where R is an “alkyl” as defined herein having the specified number of carbon atoms.

[0082] 20 Additionally, “alkylcarbonyl” shall mean same as “acyl” as defined herein.

[0083] Specifically, “(Ci-C4)acyl” shall mean formyl, acetyl or ethanoyl, propanoyl, n-butanoyl, etc. Derived expressions such as “acyloxy” and “acyloxyalkyl” are to be construed accordingly.

[0084] As used herein, the expression “aryl” means substituted or unsubstituted phenyl or naphthyl. Specific examples of substituted phenyl or naphthyl include o-, p-, m-tolyl, 1,2-, 1,3-, 1,4-xylyl, 1 -methylnaphthyl, 2- methylnaphthyl, etc. “Substituted phenyl” or “substituted naphthyl” also include any of the possible substituents as further defined herein or one 30 known in the art.

[0085] As used herein, the expression "alkenyl" means a non-cyclic, straight or Foreignfiling text P24-225

[0086] - 8 -

[0087] branched hydrocarbon chain having the specified number of carbon atoms and containing at least one carbon-carbon double bond, and includes ethenyl and straight-chained or branched propenyl, butenyl, pentenyl, hexenyl, and the like. Derived expression, “arylalkenyl” and five membered 5 or six membered “heteroarylalkenyl” is to be construed accordingly.

[0088] Illustrative examples of such derived expressions include furan-2-ethenyl, phenylethenyl, 4-methoxyphenylethenyl, and the like.

[0089] As used herein, the expression “heteroaryl” includes all of the known heteroatom containing aromatic radicals. Representative 5-membered heteroaryl radicals include furanyl, thienyl or thiophenyl, pyrrolyl, isopyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, isothiazolyl, and the like.

[0090] Representative 6-membered heteroaryl radicals include pyridinyl,

[0091] 15 pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, and the like radicals.

[0092] Representative examples of bicyclic heteroaryl radicals include, benzofuranyl, benzothiophenyl, indolyl, quinolinyl, isoquinolinyl, cinnolyl, benzimidazolyl, indazolyl, pyridofuranyl, pyridothienyl, and the like radicals. “Halogen” or “halo” means chloro, fluoro, bromo, and iodo.

[0093] 20

[0094] In a broad sense, the term “substituted” is contemplated to include all permissible substituents of organic compounds. In a few of the specific embodiments as disclosed herein, the term “substituted” means substituted with one or more substituents independently selected from the group consisting of (Ci-Ce)alkyl, (C2-Ce)alkenyl, (Ci-C6)perfluoroalkyl, phenyl, hydroxy, -CO2H, an ester, an amide, (Ci-C6)alkoxy, (Ci-Ce)thioalkyl and (Ci-C6)perfluoroalkoxy. However, any of the other suitable substituents known to one skilled in the art can also be used in these embodiments.

[0095] 30 It should be noted that any atom with unsatisfied valences in the text, schemes, examples and tables herein is assumed to have the appropriate number of hydrogen atom(s) to satisfy such valences. Foreignfiling text P24-225

[0096] - 9 -

[0097] By the term “latent organo-transition metal catalyst” is meant organo- transition metal compounds that show little or no catalytic activity at a particular (usually ambient atmospheric conditions) temperature and initiate 5 such activity either upon heat or light or both. Generally, the catalytic activity of the catalyst can be kept latent for a prolonged period of time, which can range from five days or longer especially when it is stored at room temperature or lower in a dark atmosphere. Higher temperatures and / or light may accelerate the catalytic activity.

[0098] By the term “actinic radiation” or “photolytic conditions” is meant subjecting the compositions of this invention to suitable “electromagnetic radiation,” which can be emitted from a laser, a digital processing (DLP) projector, a lamp, a light emitting diode (LED), a mercury arc lamp, a fiber optic, or 15 liquid crystal display (LCD), and the like.

[0099] It will be understood that the terms “dielectric” and “insulating” are used interchangeably herein. Thus, reference to an insulating material or layer is inclusive of a dielectric material or layer and vice versa. Further, as used 20 herein, the term “organic electronic device” will be understood to be inclusive of the term “organic semiconductor device” and the several specific implementations of such devices used, for example, in electronic, automotive or other industries.

[0100] As used herein, the dielectric constant (Dk) of a material is the ratio of the charge stored in an insulating material placed between two metallic plates to the charge that can be stored when the insulating material is replaced by vacuum or air. It is also called as electric permittivity or simply permittivity. And, at times referred as relative permittivity, because it is measured 30 relatively from the permittivity of free space.

[0101] As used herein, “low-loss” is the dissipation factor (Df), which is a measure Foreignfiling text P24-225

[0102] - 10 -

[0103] of loss-rate of energy of a mode of oscillation (mechanical, electrical, or electromechanical) in a dissipative system. It is the reciprocal of quality factor, which represents the "quality" or durability of oscillation.

[0104] 5 By the term "derived" is meant that the polymeric repeating units are polymerized (formed) from, for example, polycyclic norbornene-type monomers in accordance with formulae (I), wherein the resulting polymers are ring opened metathesis polymerized (ROMP), for example, the 2,3 double bond of norbornene-type monomers are ring opened and polymerized as shown below:

[0105]

[0106] Another example of polymerization method that can be used is addition polymerization, where new monomer units add to the growing polymer molecule chain one at a time through double or triple bonds of the monomer as shown below:

[0107]

[0108] It is also noted that for the purposes of the present application the terms "cycloolefin" and "polycycloolefin" can be preferably each denoted as "norbornene" and "polynorbornene".

[0109] 30 Detailed description of the invention Foreignfiling text P24-225

[0110] - 11 -

[0111] The present invention relates to a composition comprising at least, essentially consisting of or consisting of:

[0112] a) one or more chemical compound of formula (I):

[0113] 5

[0114]

[0115] wherein

[0116] m is an integer 0, 1 or 2;

[0117] Ri, R2, R3 and R4 are the same or different and each independently selected from the group consisting of hydrogen, halogen, methyl, ethyl, linear or branched (C3-Cie)alkyl, perfluoro(Ci-Ci2)alkyl,

[0118] hydroxy(Ci-Ci6)alkyl, (C3-Ci2)cycloalkyl, (C6-Ci2)bicycloalkyl,

[0119] 15 (C7-Ci4)tricycloalkyl, (Ce-Cio)aryl, (C6-Cio)aryl(Ci-Ce)alkyl, perfluoro(Ce-Cio)aryl, perfluoro(C6-Cio)aryl(Ci-C6)alkyl, tri(Ci-Ce)alkoxysilyl and a group of formula (A):

[0120] -Z1-Aryl (A)

[0121] 20

[0122] wherein

[0123] Z1is a bond or a group selected from the group consisting of:

[0124] (CR5R6)a, O(CR5R6)a, (CR5R6)aO, (CR5R6)a-O-(CR5R6)b,

[0125] (CR5R6)a-O-(SiR5R6)b, (CR5R6)a-(CO)O-(CR5R6)b,

[0126] (CR5R6)a-O(CO)-(CR5R6)b, (CR5R6)a-(CO)-(CR5R6)b, where a and b are integers which may be the same or different and each independently is 1 to 12;

[0127] Rs and Re are the same or different and each independently selected from the group consisting of hydrogen, methyl, ethyl, linear or branched (C3- 30 Ce)alkyl, hydroxy, methoxy, ethoxy, linear or branched (C3-Ce)alkyloxy, acetoxy, (C2-Ce)acyl, hydroxymethyl, hydroxyethyl, linear or branched hydroxy(C3-Ce)alkyl, phenyl and phenoxy; Foreignfiling text P24-225

[0128] - 12 -

[0129] Aryl is phenyl or phenyl substituted with one or more of groups selected from the group consisting of methyl, ethyl, linear or branched (C3-Ce)alkyl, hydroxy, methoxy, ethoxy, linear or branched (C3-Ce)alkyloxy, acetoxy, (C2- Ce)acyl, hydroxymethyl, hydroxyethyl, linear or branched hydroxy(C3- 5 Ce)alkyl, phenyl and phenoxy;

[0130] b) a catalyst, preferably a transition metal containing catalyst compound;

[0131] (c) a photoactive compound represented by formula (III):

[0132]

[0133] wherein

[0134] 15

[0135] Y is halogen or hydrogen; and

[0136] R30 and R31 are the same or different and independently of each other selected from the group consisting of hydrogen, methyl, ethyl, linear or branched (C3-Ci2)alkyl, (C3-Ci2)cycloalkyl, (C6-Ci2)bicycloalkyl,

[0137] (C7-Ci4)tricycloalkyl, (Ce-Cio)aryl, (C6-Cio)aryl(Ci-C3)alkyl, (Ci-Ci2)alkoxy, 20

[0138] (C3-Ci2)cycloalkoxy, (C6-Ci2)bicycloalkoxy, (C7-Ci4)tricycloalkoxy,

[0139] (C6-Cio)aryloxy(Ci-C3)alkyl and (Ce-Cio)aryloxy; and

[0140] (d) a silicone-based surfactant.

[0141] - Composition

[0142] It is believed that preferably, the compositions of this invention are stable at temperatures ranging from room temperature to 80 °C, thus offering excellent shelf-life stability. As used herein, “stable” means the composition of this invention remains clear without increase of any viscosity when kept at 30

[0143] temperatures ranging from room temperature to 80 °C, especially when kept in a dark atmosphere, such as for example, in amber or brown colored Foreignfiling text P24-225

[0144] - 13 -

[0145] containers in the absence of any light. Accordingly, in some embodiments, the composition of this invention exhibits no viscosity change when stored at temperatures below 80 °C for a period of more than thirty (30) days.

[0146] 5 Accordingly, in some embodiments, the composition of this invention exhibits less than five (5) percent viscosity increase when stored at temperatures below 80 °C for a period of more than forty (40) days. In some other embodiments, the composition of this invention exhibits less than ten (10) percent viscosity change when stored at temperatures below 80 °C for a period of sixty (60) days to ninety (90) days.

[0147] In some other embodiments, the composition of this invention exhibits less than twenty (20) percent viscosity change when stored at temperatures below 80 °C for a period of one-hundred twenty (120) days to one-hundred 15 eighty (180) days. In some other embodiments, the composition of this invention exhibits less than two (2) percent viscosity change when stored at ambient temperatures, for example from about 20 °C to 25 °C for an extended period of time, which may range from about one-hundred twenty (120) days to three hundred (300) days or longer.

[0148] 20

[0149] That is, the viscosity of the composition remains essentially unchanged when stored at ambient temperature conditions, yet the composition undergoes mass polymerization as soon as it is exposed to suitable actinic radiation as evidenced by UV-DSC measurements which indicated that the heat of polymerization remained unchanged even after a composition is stored for an extended period of time as disclose hereinabove.

[0150] The monomers employed in the composition of this invention are themselves known in the literature or can be prepared by any of the known 30 methods in the art to make such or similar types of monomers.

[0151] In addition, the monomers as described herein readily undergo mass Foreignfiling text P24-225

[0152] - 14 -

[0153] polymerization, i.e., in their neat form without use of any solvents when polymerized under mass ring open metathesis polymerization (ROMP) conditions using certain transition metal catalysts, such as for example, organo-ruthenium and organo-osmium compounds. See for example, R. H.

[0154] 5 Grubbs et al., Handbook of Metathesis, Ed.: Wiley-VCH, Weinheim, Germany, 2003, R. H. Grubbs et al., Acc. Chem. Res. 2001, 34, 18-29, R. H. Grubbs et al., Angew. Chem. Int. Ed., 2006, 45, 3760-3765. Or they can also be polymerized under addition polymerization conditions using certain multi-component catalyst containing a group 10 transition metal complex procatalyst compound with a cocatalyst or activator, such as for example, a palladium complex procatalyst compound with a photo-acid generator. See for example, US7875686B2. The term “mass polymerization” as used herein shall have the generally accepted meaning in the art. That is, a polymerization reaction that is generally carried out 15 substantially in the absence of a solvent.

[0155] In some cases, however, a small proportion of solvent is present in the reaction medium. For example, such small amounts of solvent may be used to dissolve the catalyst and / or the activator or convey the same to the 20 reaction medium. Also, some solvent may be used to reduce the viscosity of the monomer. The amount of solvent that can be used in the reaction medium may be in the range of 0 to 5 weight percent based on the total weight of the monomers employed. Any of the suitable solvents that dissolves the catalyst, activator and / or monomers can be employed in this invention. Examples of such solvents include alkanes, cycloalkane, toluene, THF, dichloromethane, dichloroethane, and the like.

[0156] Advantageously, it has now been found that one or more of the monomers themselves can be used to dissolve the catalyst as well as the activator and 30 thus avoiding the need for the use of solvents. In addition, one monomer can itself serve as a solvent for the other monomer and thus eliminating the need for an additional solvent. For example, if first monomer of formula (I) Foreignfiling text P24-225

[0157] - 15 -

[0158] is a solid at room temperature, then the second monomer of formula (I), which is liquid at room temperature can be used as a solvent for the first monomer of formula (I) which is a solid or vice versa. Therefore, in such situations more than one monomer can be employed in the composition of 5 this invention.

[0159] In general, the composition of this invention exhibits low viscosity at room temperature, which can be below 100 centipoise or lower. In some embodiments, the viscosity at room temperature of the composition of this invention is less than 80 centipoise. In some other embodiments the viscosity at room temperature of the composition of this invention is in the range from about 10 to 100 centipoise. In yet some other embodiments the viscosity at room temperature of the composition of this invention is lower than 70 cP, lower than 60 cP, lower than 40 cP, lower than 20 cP at room 15 temperature. In some other embodiments it may even be lower than 10 cP and may vary from as low as 3 cP to 9 cP at room temperature.

[0160] Accordingly, the compositions of this invention can also include other high refractive polymeric materials and / or nanoparticles which will bring about 20 such intended benefit. Examples of such polymers include without any limitation, poly(-methylstyrene), poly(vinyl-toluene), copolymers of - methylstyrene and vinyl-toluene, and the like. Examples of such nanoparticles include without any limitation, organic or inorganic nanoparticles in a size range of 1-100 nm including materials like crosslinked poly(styrene), crosslinked poly(methacrylates), metal oxides (e.g. zinc oxide, magnesium oxide, titanium oxide), silicon, silicon oxide, silicon nitride, stabilizer and luminescent materials (e.g. Ill-V semiconductor nanoparticles like indium phosphide).

[0161] 30 - Chemical compound of formula (I)

[0162] In some embodiments of the present invention, the refractive index of the monomers of formula (I) is 1.5 or more. In some other embodiments the Foreignfiling text P24-225

[0163] - 16 -

[0164] refractive index of the monomers of formula (I) is in the range from about 1.5 to 1.6. In yet some other embodiments the refractive index of the monomers of formula (I) is 1.55 or more, 1.6 or more, or 1.65 or more. In some other embodiments it may even be 1.7 or more. And preferably 2.0 or 5 less.

[0165] It is believed that the monomer(s) of formula (I) may also serve as high refractive index materials imparting high refractive index to the resulting polymeric film upon mass polymerization at a temperature and / or condition different from the application of the composition onto a desirable substrate.

[0166] When the composition of this invention contains two or more monomers, for example, they can be present in any desirable amounts that would bring about intended benefit, including either refractive index modification or 15 viscosity modification or both.

[0167] In general, the compositions in accordance with the present invention encompass the above described one or more of the monomer of formula (I) and if needed additional monomers of formula (I) distinct from each 20 other, as it will be seen below, various composition embodiments are selected to provide properties to such embodiments that are appropriate and desirable for the use for which such embodiments are directed, thus such embodiments are tailorable to a variety of specific applications.

[0168] For example, as already discussed above, proper combination of distinctive monomers of formula (I) makes it possible to tailor a composition having the desirable refractive index, viscosity and optical transmission properties. In addition, as described further herein it may be desirable to include other polymeric or monomeric materials, such as for example inorganic

[0169] 30 nanoparticles which are compatible to provide desirable optical properties depending upon the end use application. Foreignfiling text P24-225

[0170] - 17 -

[0171] Accordingly, in a preferable embodiment of the present invention, the monomer(s) of formula (I) is selected from the following:

[0172] 5

[0173]

[0174] 5-(4-phenylbutyl)bicyclo[2.2.1 ]hept-2-ene;

[0175]

[0176] 5-(3-phenylpropyl)bicyclo[2.2.1 ]hept-2-ene;

[0177]

[0178] 5-phenethylbicyclo[2.2.1 ]hept-2-ene (PENB);

[0179]

[0180] 5-decylbicyclo[2.2.1 ]hept-2-ene (DecNB);

[0181]

[0182] 5-(benzyloxy)bicyclo[2.2.1 ]hept-2-ene;

[0183] 30

[0184]

[0185] 5-(2-([1, 1 '-biphenyl]-4-yloxy)ethyl)bicyclo[2.2.1 ]hept-2-ene; Foreignfiling text P24-225

[0186] - 18 -

[0187]

[0188] 5 5-(2-([1, 1 '-biphenyl]-2-yloxy)ethyl)bicyclo[2.2.1 ]hept-2-ene (NBEtO-2- PhPh);

[0189] 5-butylbicyclo[2.2.1 ]hept-2-ene (BuNB);

[0190]

[0191] 5-hexylbicyclo[2.2.1 ]hept-2-ene (HexylNB);

[0192]

[0193] 5-octylbicyclo[2.2.1 ]hept-2-ene (OctNB);

[0194]

[0195] 5-decylbicyclo[2.2.1 ]hept-2-ene (DecNB);

[0196] 5-ethylidenebicyclo[2.2.1 ]hept-2-ene;

[0197]

[0198] 2-ethylidene-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene;

[0199] 30

[0200]

[0201] 3a,4,4a,5,8,8a,9,9a-octahydro-1 H-4, 9:5,8- Foreignfiling text P24-225

[0202] - 19 -

[0203] dimethanocyclopenta[b]naphthalene (one of trimers of cyclopentadiene, TCPD1, also known as CPD3);

[0204] 5

[0205]

[0206] 5-norbornenylmethyleugenyl acetate (EuAcNB);

[0207]

[0208] 5-norbornenylmethyleugenol (EuOHNB);

[0209] (bicyclo[2.2.1 ]hept-5-en-2-ylmethoxy)(methyl)diphenylsilane

[0210] (NBCH2OSiMePh2);

[0211]

[0212] (bicyclo[2.2.1 ]hept-5-en-2-ylmethoxy)(ethyl)diphenylsilane;

[0213] 30 Foreignfiling text P24-225

[0214] 5

[0215]

[0216] (bicyclo[2.2.1]hept-5-en-2-ylmethoxy)(ethyl)(methyl)(phenyl)silane;

[0217] (bicyclo[2.2.1 ]hept-5-en-2-ylmethoxy)dimethyl(phenyl)silane;

[0218] Si(OCH3)3

[0219]

[0220] bicyclo[2.2.1 ]hept-5-en-2-yltrimethoxysilane (TMSNB);

[0221] bicyclo[2.2.1]hept-5-en-2-yltriethoxysilane (NBSi(OC2H5)3);

[0222]

[0223] bicyclo[2.2.1 ]hept-5-en-2-yl(tert-butoxy)dimethoxysilane;

[0224] Si(OMe)3

[0225]

[0226] (2-(bicyclo[2.2.1 ]hept-5-en-2-yl)ethyl)trimethoxysilane;

[0227] 30 Foreignfiling text P24-225

[0228] - 21 -

[0229] OH

[0230] OH

[0231] 5 NB(MeOH)2;

[0232]

[0233] tetracyclododecene (TD);

[0234]

[0235] 2-phenyl-tetracyclododecene (PhTD);

[0236] 2-benzyl-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene;

[0237]

[0238] 2-phenethyl-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene (PETD);

[0239] 30 Foreignfiling text P24-225

[0240] 2-butyl-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene 5 (ButylTD);

[0241] 2-hexyl-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene (HexylTD);

[0242] 2-octyl-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene (OctylTD);

[0243] 2-decyl-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene (DecylTD);

[0244] 2-cyclohexyl-tetracyclododecene (CyclohexylTD);

[0245]

[0246] 2- cyclohexylmethyl-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8- dimethanonaphthalene;

[0247] 30 Foreignfiling text P24-225

[0248]

[0249] 5 2- cyclohexylethyl-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8- dimethanonaphthalene;

[0250] (1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalen-2-yl)methyl acetate (TDMeOAc);

[0251]

[0252] tetracyclododecadiene (TDD) ; and

[0253]

[0254] 1, 1,3,3,-Tetramethyl-1,3-bis-[2-(5-norbornen-2-yl)-ethyl]-disiloxan (CL1 ).

[0255] As noted, preferably, the monomer of formula (I) is having a refractive index of at least 1.5. The composition is in a clear liquid form at room temperature.

[0256] The total amount of the monomer of formula (I) is in the range from 80 to 99.99 wt % based on the total amount of the composition. Preferably it is in the range from 90 to 99.99 wt %, more preferably from 95 to 99.99 wt %, even more preferably it is 97 to 99.99 wt %.

[0257] 30

[0258] - Catalyst: organo-ruthenium compound Foreignfiling text P24-225

[0259] - 24 -

[0260] As noted, the composition of this invention contains at least one catalyst, preferably a transition metal containing catalyst compound.

[0261] In a preferred embodiment, when said catalyst is transition metal containing catalyst compound, preferably the transition metal containing catalyst 5 compound is an organo-ruthenium compound represented by formula (II):

[0262]

[0263] wherein

[0264] 15 c and d are integers from 0 to 5;

[0265] Z is oxygen or sulfur;

[0266] R7 is selected from the group consisting of hydrogen, (C1-C20)alkyl,

[0267] (C2-C20)alkenyl, (C2-C20)alkynyl and (C6-C10)aryl; and

[0268] R8, R9, R10 and R11 are the same or different and each independently 20 selected from the group consisting of hydrogen, halogen, (C1-C16)alkyl, (C1-C16)alkoxy, (C1-C16)perfluoroalkyl, (C3-C7)cycloalkyl, (C2-C16)alkenyl, (C6-C14)aryl, (C6-C14)perfluoroaryl,

[0269] (C3-C12)heterocyclyl, -OR16, -NO2, -COOH, -COOR16, -CONR16R17, -SO2NR16R17, -SO2R16, -CHO, -COR16,

[0270] wherein R16 and R17 are the same or different and each independently selected from the group consisting of (C1-C6)alkyl, (C1-C6)perfluoroalkyl, (C6-C14)aryl, (C6-C14)perfluoroaryl; or wherein

[0271] two or more of R8, R9, R10 and R11 taken together with the carbon atoms to which they are attached to form a substituted or unsubstituted, fused 30 (C4-C8)carbocyclic ring, or a substituted or unsubstituted, fused aromatic ring; Foreignfiling text P24-225

[0272] - 25 -

[0273] each R12, R13 and R14 may be the same or different and independently of the other selected from the group consisting of hydrogen, halogen, (C1-C16)alkyl, (C1-C16)alkoxy, (C1-C16)perfluoroalkyl, (C3-C7)cycloalkyl, (C2-C16)alkenyl, (C6-C14)aryl, (C6-C14)perfluoroaryl,

[0274] 5 (C3-C12)heterocyclyl, -OR16, -NO2, -COOH, -COOR16, -CONR16R17, -SO2NR16R17, -SO2R16, -CHO, -COR16, wherein R16 and R17 are the same or different and each independently selected from the group consisting of (C1-C6)alkyl, (C1-C6)perfluoroalkyl, (C6-C14)aryl, (C6-C14)perfluoroaryl;

[0275] R15 is selected from the group consisting of (Ci -Cie)alkyl,

[0276] (Ci-Ci6)perfluoroalkyl, (C3-Ci6)cycloalkyl, (Ce-Ci4)aryl, (Ce-Ci4)perfluoroaryl and (C3-Ci2)heterocyclyl;

[0277] Ar1 and Ar2 are the same or different and each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl and substituted or unsubstituted naphthyl, wherein 15 each of said substituents are independently selected from the group consisting of methyl, ethyl and linear or branched (C3-C6)alkyl.

[0278] In a preferred embodiment, when the catalyst is an organo-ruthenium compound represented by formula (II), that would bring about the mass 20 polymerization as described herein under ROMP conditions when the composition is subjected to suitable actinic radiation. Generally, such an organo-ruthenium compound represented by formula (II), is “latent” and become active only under certain conditions. Again, as used herein the term “latent” means that the organo-ruthenium catalyst used in the composition of this invention remains inactive for a prolonged period of time when the composition of this invention is stored at ambient conditions to temperatures up to 80 °C. Accordingly, in some embodiments the organo-ruthenium catalysts remain latent for a period of more than thirty (30) days when stored at temperatures below 80 °C. In some other embodiments, the organo- 30 ruthenium catalyst remains latent for a period of forty (40) days to ninety (90) days when stored at temperatures below 50 °C. Foreignfiling text P24-225

[0279] - 26 -

[0280] Generally, any of the latent organo-ruthenium compound represented by formula (II), that would bring about ring open metathesis polymerization of the monomers of formula (I) can be employed in the composition of this invention. Interestingly, it has now been found that organo-ruthenium 5 compounds of formula (II) are very stable at temperatures from about 25 °C (i.e., ambient conditions) up to a temperature of about 80 °C and can be stored as such or in the presence of one or more monomers of formula (I) for several days even including up to three to six months or even longer. That is, the organo-ruthenium compounds of formula (II) preferably serve as latent catalysts that are stable at or near room temperature to elevated temperatures of up to 80 °C and yet can be readily activated by a variety of conditions, including without any limitation thermal, acid, light and chemical activation only when needed. The chemical activation may include use of thermal acid generator or photo acid generators.

[0281] 15

[0282] Several of the latent catalysts that are known in the literature are not stable under the conditions specified herein and most of them do not exhibit the required shelf-life stability as described herein. See for example, Grubbs, et al., Organometallics, 2011, 30 (24): 6713-6717; Sutar et al., Angew. Chem.

[0283] 20 Int. Ed. 2016, 55, 764-767; Leitgeh, et al., Monatsh Chem (2014) 145:1513- 1517; van Hensbergen, et al., J. Mater. Chem. C. 2015, 3, 693-702; Grubbs, et al., J. Am. Chem. Soc., 2009, 131, 203802039; Zak, et al., Eur. J. Inorg. Chem., 2014, 1131-1136; Gawin, et al., ACS Catal. 2017, 7, 5443-5449. Further examples of such catalysts can also be found in U. S. Patent No.

[0284] 9,328,132, pertinent portions of which are incorporated herein by reference. Accordingly, the compositions encompassing the organo-ruthenium compounds of formula (II) provide hitherto unattainable advantages in various applications as described herein.

[0285] 30 According to the present invention, such an organo-ruthenium compound can be any publicly available one. The organo-ruthenium compound like described in US 11230624 B2 may also be used. Preferably, it is a compound Foreignfiling text P24-225

[0286] of formula (II), wherein:

[0287] Z is oxygen;

[0288] R7 is hydrogen;

[0289] R8, R9, R10 and R11 are the same or different and each independently 5 selected from the group consisting of hydrogen, methyl, ethyl and -NO2;

[0290] R12, R13 and R14 are the same or different and each independently selected from the group consisting of hydrogen, methyl, ethyl and -NO2;

[0291] R15 is selected from the group consisting of methyl, ethyl and cyclohexyl; Ar1 and Ar2 are the same or different and each independently selected from the group consisting of phenyl, 2,6-dimethylphenyl, 2,6-diethylphenyl, 2,6-di(isopropyl)phenyl and 2,4,6-trimethylphenyl.

[0292] Accordingly, a few of the exemplary latent catalysts, which are within the scope of organo-ruthenium compounds of formula (II), without any limitation 15 maybe selected from the group consisting of:

[0293] 20

[0294]

[0295] [1,3-bis(2,6-diisopropylphenyl)-2-imidazolidinylidene]{2-[(E)-({2-[methylthio- KS]phenyl}imino-KN)methyl]phenoxido-KO}[2-(oxido-KO)benzylidene- KC]ruthenium(ll) (Ru-1);

[0296] 30 Foreignfiling text P24-225

[0297] 5

[0298]

[0299] [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]{2-[(E)-({2- [isopropylthio-KS]phenyl}imino-KN)methyl]phenoxido-KO}[2-(oxido- KO)benzylidene-KC]ruthenium(ll) (Ru-2);

[0300]

[0301] [1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]{2-[(E)-({2- [cyclohexylthio-KS]phenyl}imino-KN)methyl]phenoxido-KO}[2-(oxido- KO)benzylidene-KC]ruthenium(ll) (Ru-3); and

[0302] 30 Foreignfiling text P24-225

[0303] 5

[0304]

[0305] [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]{2-[(E)-({2-[methylthio- KS]phenyl}imino-KN)methyl]phenoxido-KO}[2-(oxido-KO)benzylidene- KC]ruthenium(ll) (Ru-4).

[0306] Interestingly, it has now been found that the organo-ruthenium compounds 15 of formula (II) can be activated by certain of the known photoactive compounds (photosensitizer) when subjected to suitable photolytic conditions thereby facilitating mass polymerization of one or more monomers of the formula (I) contained in the composition of this invention under ROMP conditions as described herein.

[0307] 20

[0308] The total amount of the organo-ruthenium compound is in the range from 0.0001% to 1.5 wt % based on the total amount of the composition. Preferably it is in the range from 0.005 to 0.5 wt %, more preferably from 0.01 to 0.1 wt %, even more preferably it is 0.02 to 0.06 wt %.

[0309] - Catalyst: multi-component catalyst containing a group 10 transition metal complex procatalyst compound with a cocatalyst or activator

[0310] As noted, the composition of this invention contains at least one catalyst, 30 preferably a transition metal containing catalyst compound.

[0311] In a preferred embodiment, when catalyst is transition metal containing catalyst compound, preferably it is a multi-component catalyst containing a Foreignfiling text P24-225

[0312] - 30 -

[0313] group 10 transition metal complex procatalyst compound with a cocatalyst or activator, that would bring about the mass polymerization as described herein under addition polymerization conditions when the composition is subjected to suitable actinic radiation. The catalyst for polymerizing

[0314] 5 monomer(s) of formula (I) can be prepared as a multi-component catalyst prepared in situ by mixing a group 10 transition metal complex procatalyst compound with a cocatalyst or activator in the presence of the desired monomer(s) to be polymerized, along with the photoactive compound represented by formula (III). It is believed that when this mixture is subjected to suitable actinic radiation, the photoactive compound represented by formula (III) absorbs the light and transfers the energy from its excited state onto the activator / cocatalyst. By cocatalyst is meant that the group 10 transition metal complex procatalyst compound is converted to an active catalyst by a reaction with the activator / cocatalyst. The

[0315] 15 activator / cocatalyst in the excited state is unstable and decomposes in a multi-step cascade to produce a proton. This proton then activates the group 10 transition metal complex procatalyst compound, which allows the addition polymerization reaction of monomer(s) of formula (I) to proceed under appropriate temperature conditions.

[0316] 20

[0317] Preferably, group 10 metal of the group 10 transition metal complex procatalyst compound is selected from nickel, palladium, and platinum, and with palladium being the most preferred metal. Representative procatalyst compounds include, but are not limited to, palladium (hexafluoroacetylacetonate)2, palladium(hexafluoroacetylacetonate)2 triisopropylphosphine, palladium acetate, (allyl)palladium (tricyclohexylphosphine)triflate, (allyl)palladium(triisopropylphosphine)triflate, (allyl)palladium(tricyclohexylphosphine)trifluoroacetate, (allyl)

[0318] 30 palladium(triisopropylphosphine)trifluoroacetate, (acetonitrile)bis (triisopropylphosphine)palladium(acetate)tetrakis(penta fluorophenyl) borate, (acetonitrile)bis(tricyclohexylphosphine)palladium(acetate)tetrakis Foreignfiling text P24-225

[0319] - 31 -

[0320] (pentafluorophenyl) borate, [bis(triisopropylphosphine)(hydrido) palladium(acetonitrile)]tetrakis (pentafluorophenyl) borate, bis (triisopropylphosphine)palladium(ll)bis(acetate) and bis(tricyclohexylphosphine) palladium(II) bis(acetate).

[0321] 5

[0322] Cocatalysts or activator compounds can be photo-acid generators. Said photo-acid generators can be selected from, but are not limited to, sulfonium salt-type photo-acid generators, iodonium salt-type photo-acid generators, non-ionic photo-acid generators and other photo-acid generators. Representative sulfonium salt-type photo-acid generators include Triphenylsulfonium Hexafluoroantimonate, Diphenyl[4- (phenylthio)phenyl]sulfonium Hexafluoroantimonate, Diphenyl[4- (phenylthio)phenyl]sulfonium Tetrakis(pentafluorophenyl)borate, [1,1'- B ipheny l]-4-y l[4-[[ 1, 1 '-biphenyl]-4-ylthio]phenyl](phenyl)sulfonium

[0323] 15 Tetrakis(perfluorophenyl)borate, (9-Oxo-9H-thioxanthen-2-yl)[4-[(9-oxo-9H- thioxanthen-2-yl)thio]phenyl](phenyl)sulfonium Tetrakis(perfluorophenyl)borate, Triphenylsulfonium Hexafluorophosphate, Diphenyl[4-(phenylthio)phenyl]sulfonium Hexafluorophosphate, (4- Hydroxyphenyl)dimethylsulfonium Hexafluorophosphate, Tri-p- 20 tolylsulfonium Hexafluorophosphate, (Thiodi-4, 1 - phenylene)bis(diphenylsulfonium) Bis(hexafluorophosphate), Triphenylsulfonium Tetrafluoroborate, Triphenylsulfonium

[0324] T rifluoromethanesulfonate, T ri-p-tolylsulfonium T rifluoromethanesulfonate, Triphenylsulfonium Nonafluoro-1 -butanesulfonate, Triphenylsulfonium 10- Camphorsulfonate, Triphenylsulfonium Chloride, Triphenylsulfonium Bromide. Representative Iodonium salt-type photo-acid generators include Iodonium, diphenyl-, 4,4’-di-C10-13-alkyl derivs, tetrakis(2,3,4,5,6- pentafluorophenyl)borates (Silcolease® UV CATA 243, Elkem Silicones), [4-(Octyloxy)phenyl](phenyl)iodonium Hexafluoroantimonate, [4-[(2- 30 Hydroxytetradecyl)oxy]phenyl]phenyliodonium Hexafluoroantimonate, Bis(4-tert-butylphenyl)iodonium Hexafluoroantimonate, 4-lsopropyl-4'- methyldiphenyliodonium Tetrakis(pentafluorophenyl)borate, Bis(4-tert- Foreignfiling text P24-225

[0325] - 32 -

[0326] butylphenyl)iodonium Hexafluorophosphate, (4-lsobutylphenyl)(p- tolyl)iodonium Hexafluorophosphate, Bis(4-methylphenyl)iodonium Hexafluorophosphate, Diphenyliodonium Hexafluorophosphate, Bis(4-tert- butylphenyl)iodonium Tetrafluoroborate, Diphenyliodonium

[0327] 5 Tetrafluoroborate, Bis(4-tert-butylphenyl)iodonium Nonafluoro-1 - butanesulfonate, Diphenyliodonium Trifluoromethanesulfonate, Diphenyliodonium Hexafluoroarsenate, (4-lsopropylphenyl)(p-tolyl)iodonium Trifluorotris(perfluoroethyl)phosphate(V), Bis(4-tert-butylphenyl)iodonium Chloride. Representative non-ionic photo-acid generators include N- Hydroxynaphthalimide Trifluoromethanesulfonate, 2-(4-Methoxyphenyl)- 4,6-bis(trichloromethyl)-1, 3, 5-triazine, 2-(1,3-Benzodioxol-5-yl)-4,6- bis(trichloromethyl)-1,3, 5-triazine, 2-[2-(Furan-2-yl)vinyl]-4,6- bis(trichloromethyl)-1,3, 5-triazine, 2-[2-(5-Methylfuran-2-yl)vinyl]-4,6- bis(trichloromethyl)-1,3, 5-triazine, 2-(4-Methoxystyryl)-4,6- 15 bis(trichloromethyl)-1,3, 5-triazine, 2-(3,4-Dimethoxystyryl)-4,6- bis(trichloromethyl)-1,3, 5-triazine. Representative other types of photo-acid generators include 4-Nitrobenzenediazonium Tetrafluoroborate, (Cumene)cyclopentadienyliron(ll) Hexafluorophosphate, lithium tetrakis(pentafluorophenyl) borate, N, N-Dimethylanilinium

[0328] 20 Tetrakis(pentafluorophenyl)borate. More examples of procatalyst compounds and cocatalysts or activator compounds can be found in US20060041093A1.

[0329] The total amount of the multi-component catalyst containing a group 10 transition metal complex procatalyst compound with a cocatalyst or activator is in the range from 0.0001 % to 1.5 wt % based on the total amount of the composition. Preferably it is in the range from 0.005 to 1.2 wt %, more preferably from 0.01 to 1.0 wt %, even more preferably it is 0.1 to 0.8 wt%.

[0330] 30

[0331] - Photoactive compound represented by formula (III) Foreignfiling text P24-225

[0332] - 33 -

[0333] According to the present invention, the composition contains a photoactive compound represented by formula (III). It is configured to bring the catalyst into its active form.

[0334] 5 For the photoactive compound, a class of substituted xanthone derivatives, can be used for this purpose. Preferably the photoactive compound is illustrated by structural formula (III):

[0335]

[0336] wherein

[0337] Y is halogen or hydrogen; and

[0338] R30 and R31 are the same or different and independently of each other 15

[0339] selected from the group consisting of hydrogen, methyl, ethyl, linear or branched (C3-Ci2)alkyl, (C3-Ci2)cycloalkyl, (C6-Ci2)bicycloalkyl,

[0340] (C7-Ci4)tricycloalkyl, (Ce-Cio)aryl, (C6-Cio)aryl(Ci-C3)alkyl, (Ci-Ci2)alkoxy, (C3-Ci2)cycloalkoxy, (C6-Ci2)bicycloalkoxy, (C7-Ci4)tricycloalkoxy,

[0341] (C6-Cio)aryloxy(Ci-C3)alkyl and (Ce-Cio)aryloxy.

[0342] 20

[0343] In some embodiments, the compound of formula (III) have the following: Y is chlorine, bromine or hydrogen; and

[0344] R30 and R31 are the same or different and independently of each other selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, iso-propyl, phenyl, cyclohexyl, methoxy, ethoxy, n- propoxy and phenoxy. Representative examples of the compounds of formula (VII), without any limitation, may be listed as follows:

[0345] 30 Foreignfiling text P24-225

[0346] - 34 -

[0347] 5

[0348]

[0349] 1-chloro-4-methoxy-9H-thioxanthen-9-one;

[0350]

[0351] 1-chloro-4-ethoxy-9H-thioxanthen-9-one;

[0352] 15

[0353]

[0354] 1-chloro-4-propoxy-9H-thioxanthen-9-one; 20

[0355]

[0356] 1-chloro-2-propoxy-9H-thioxanthen-9-one;

[0357]

[0358] 1-chloro-2-ethoxy-9H-thioxanthen-9-one; 30 Foreignfiling text P24-225

[0359]

[0360] 5 1-chloro-2-methoxy-9H-thioxanthen-9-one;

[0361]

[0362] 1-chloro-4-methyl-9H-thioxanthen-9-one;

[0363] 15

[0364]

[0365] 1-chloro-4-ethyl-9H-thioxanthen-9-one;

[0366] 20

[0367]

[0368] 1-bromo-4-propoxy-9H-thioxanthen-9-one O Cl

[0369] cc

[0370]

[0371] Th

[0372] 1 -chloro-4-phenoxy-9H-thioxanthen-9-one; and 30 Foreignfiling text P24-225

[0373]

[0374] 5

[0375] Isopropyl-9H-thioxanthen-9-one.

[0376] It is believed that by employing a suitable combination of catalyst with one or more of a photoactive compound can trigger the mass polymerization of the monomers when the composition is subjected to a suitable actinic radiation, generally at wavelengths of from about 240 nm to 410 nm. In a preferred embodiment, when organo-ruthenium compound is used as the catalyst, Y in photoactive compound is halogen, the composition undergoes mass ring open-metathesis polymerization (ROMP) to form a transparent film or an object. In another preferred embodiment, when the catalyst is a multi15

[0377] component catalyst containing a group 10 transition metal complex procatalyst compound with a cocatalyst or activator, Y in photoactive compound is hydrogen, the composition undergoes addition polymerization to form a transparent film or an object. For that purpose, the combination of an organo-ruthenium compound of formula (II) and a photoactive compound 20

[0378] of formular (III) when Y is halogen is especially suitable. And the combination of a multi-component catalyst containing a group 10 transition metal complex procatalyst compound with a cocatalyst or activator and a photoactive compound of formular (III) when Y is hydrogen is especially suitable.

[0379] Preferably, the total amount of the photoactive compound represented by formula (III) is in the range from 0.0001 to 1.0 wt % based on the composition. Preferably it is from 0.001 to 0.5 wt %, more preferably it is from 0.002 to 0.4 wt %, further preferably it is from 0.005-0.2 wt %.

[0380] 30

[0381] In some embodiments the composition of this invention undergoes mass Foreignfiling text P24-225

[0382] - 37 -

[0383] polymerization when exposed to suitable UV irradiation to form a substantially transparent film. The monomers undergo mass polymerization to form films which are substantially transparent to visible light. That is, most of the visible light is transmitted through the film. In some embodiments such 5 film formed from the composition of this invention exhibits a transmission of equal to or higher than 90 percent of the visible light. In some other embodiments such film formed from the composition of this invention exhibits a transmission of equal to or higher than 95 percent of the visible light.

[0384] Accordingly, in some embodiments the compositions of this invention can be mass polymerized to form solid objects, such as transparent films, in less than five seconds after exposure to suitable actinic radiation. In some other embodiments the compositions of this invention can be mass polymerized to form solid objects, such as transparent films, in less than ten 15 seconds after exposure to suitable actinic radiation. In yet some other embodiments the compositions of this invention can be mass polymerized to form solid objects, such as transparent films, in one to ten seconds after exposure to suitable actinic radiation; in two to nine seconds, in three to eight seconds, in four to seven seconds, and so on.

[0385] 20

[0386] In yet other embodiments the composition of this invention undergoes mass polymerization when exposed to suitable UV irradiation at a temperature from 80 °C to 100 °C to form a substantially transparent film or an object.

[0387] In some embodiments the photoactive compound represented by formula (III), can be activated at certain wavelength of the electromagnetic radiation which can generally range from about 240 nm to 400 nm. Accordingly, any of the compounds which are active in this electromagnetic radiation can be employed in the compositions of this invention. In some embodiments the wavelength of the radiation to activate the photoactive compound

[0388] 30 represented by formula (III), is 260 nm. In some other embodiments the wavelength of the radiation to activate the photoactive compound is 310 nm. In yet some other embodiments the wavelength of the radiation to Foreignfiling text P24-225

[0389] - 38 -

[0390] activate the photoactive compound is 395 nm.

[0391] However, any of the other known photoactive compounds which can activate the catalyst employed herein can also be used in the composition 5 of this invention. All such compounds are part of this invention.

[0392] - Silicone-based surfactant

[0393] The composition of this invention comprises a silicone-based surfactant. It is believed that the using the surfactant in the composition containing other ingredients defined in claims may solve one or more of the technical problems as defined in the section of “Summary of the Invention” above. As one preferable embodiment of this invention, the silicone-based surfactant has a siloxane bond represented by following chemical formula (VI).

[0394] ■ CH3

[0395] (CH3)3Si — o - Si - O - SiSi(CH3)3

[0396] R(VI)

[0397] X(VI)

[0398] (VI)

[0399]

[0400] Wherein

[0401] R(VI) is linear or branched (Ci-Cso)alkyl;

[0402] X(VI) is an integer from 1-100;

[0403] As one preferable embodiment of this invention, the silicone-based surfactant is an aralkyl modified silicone represented by following chemical formula (IV).

[0404] 30 Foreignfiling text P24-225

[0405] - 39 -

[0406] CH3CH3

[0407] (CH3)3Si O Si(CH3)3

[0408] (CH2)m(iV)

[0409] 5 -> x(l V)

[0410] L * 'VM Jy(IV)

[0411]

[0412] (IV)

[0413] wherein

[0414] R(IV)-1 is an aralkyl group. Aryl is phenyl or phenyl substituted with one or more of groups selected from the group consisting of methyl, ethyl, linear or branched (C3-Ce)alkyl, hydroxy, methoxy, ethoxy, linear or branched (C3- Ce)alkyloxy, acetoxy, (C2-Ce)acyl, hydroxymethyl, hydroxyethyl, linear or branched hydroxy(C3-Ce)alkyl, phenyl and phenoxy;

[0415] 15 R(IV)-2 is linear or branched (Ci-Cso)alkyl;

[0416] m(IV) is an integer from 1-100;

[0417] x(IV) is an integer from 1-100;

[0418] y(IV) is an integer from 1-100;

[0419] 20 As one preferable embodiment of this invention, silicone-based surfactant is a polyether modified silicone represented by following chemical formula (V).

[0420] CH3" CH3 "

[0421] (CH3)3Si — O - Si - O -Si — O--Si(CH3)3

[0422] (CH2)m(V)

[0423] CH3x(V)

[0424] o

[0425] 30

[0426] y(V)

[0427]

[0428] (V) Foreignfiling text P24-225

[0429] - 40 -

[0430] wherein

[0431] R(V)-1 and R(V)-2 are the same or different and each independently selected from, hydrogen and linear or branched (Ci-Cso)alkyl;

[0432] m(V) is an integer from 1-100;

[0433] 5 n(V) is an integer from 1-100;

[0434] x(IV) is an integer from 1-100;

[0435] y(IV) is an integer from 1-100.

[0436] When organo-ruthenium compound is used as the catalyst, Y in photoactive compound is halogen, it is preferable that the silicone-based surfactant is an aralkyl modified silicone or a polyether modified silicone, more preferably an aralkyl modified silicone. When the catalyst is a multi-component catalyst containing a group 10 transition metal complex procatalyst compound with a cocatalyst or activator, Y in photoactive compound is hydrogen, it is 15 preferable that the silicone-based surfactant is an aralkyl modified silicone.

[0437] The surface tension of the composition can be lowered by using silicone- based surfactant as additives in the composition. However, it is not only the surface tension the controls the behavior of a printed film. The adhesion 20 also needs to be balanced so that the film stays in the shape that was printed. Also, the additive must not interfere with the (UV-initiated) curing reaction of the printed ink. Also, the additive should not have a negative impact on the optical and electronic properties of the film. It is believed that by adding the silicone-based surfactant to the composition, the Dk value of the composition is kept low, and the silicone-based surfactant solves all the problems mentioned above.

[0438] Representative examples of the silicone-based surfactant, without any limitation, may be listed as follows: BYK®-300, BYK®-302, BYK®-306, BYK 30 ®-307, BYK®-310, BYK®-315, BYK®-322, BYK®-323, BYK®-325, BYK®- 330, BYK®-331, BYK®-333, BYK®-337, BYK®-341, BYK®-342, BYK®-344, Foreignfiling text P24-225

[0439] - 41 -

[0440] BYK®-345, BYK®-347, BYK®-348, BYK®-349, BYK®-370, BYK®-375, BYK® -377, BYK®-378, BYK®-UV 3500, BYK®-UV 3510, BYK®-UV 3570, BYK®- Silclean 3700, and BYK®-Silclean 3720 (all manufactured by BYKJapan KK).

[0441] 5

[0442] Accordingly, in a preferable embodiment of the present invention, when organo-ruthenium compound is used as the catalyst, Y in photoactive compound is halogen, without any limitation, it is preferable that the silicone- based surfactant is an aralkyl modified silicone selected from DISPER BYK ®-322, BYK®-323 or a polyether modified silicone selected from DISPER BYK®-300, BYK®-302, BYK®-306, BYK®-307, BYK®-330, BYK®-331, BYK® -333, BYK®-342 and BYK®-378, more preferably it is an aralkyl modified silicone selected from DISPER BYK®-322 and BYK®-323. In another 15 preferable embodiment of the present invention, when the catalyst is a multicomponent catalyst containing a group 10 transition metal complex procatalyst compound with a cocatalyst or activator, Y in photoactive compound is hydrogen, it is preferable that the silicone-based surfactant is an aralkyl modified silicone selected from DISPER BYK®-322 and BYK®- 20 323.

[0443] Preferably, the total amount of the silicone-based surfactant is in the range from 0.0001 to 2.0 wt % based on the composition. Preferably it is from 0.001 to 1.7 wt %, more preferably it is from 0.01 to 1.6 wt %, further preferably it is from 0.1 to 1.5 wt %.

[0444] - Additives

[0445] The compositions in accordance with the present invention may further contain optional additives as may be useful for the purpose of improving 30 properties of both the composition and the resulting object made therefrom.

[0446] Here, additive is different from the component that are described above. Such optional additives for example may include crosslinking agents, Foreignfiling text P24-225

[0447] - 42 -

[0448] stabilizers, antioxidants, synergists, viscosity modifiers, binders, solvents, and the like, and any combination of any of these.

[0449] As one embodiment of the composition of this invention, the content of such 5 additive is 0-15 wt % (preferably 0.01-10 wt %; more preferably 0.1-5 wt %;

[0450] further preferably 0.1-1 wt %) based on the composition. It is another preferable embodiment that the composition of this invention does not comprise such additive (0.0 wt %) based on the composition.

[0451] -Use of the composition

[0452] The present invention may relate to use of the composition of the present invention for fabricating a film, preferably for fabricating an optical film for an electronic device.

[0453] 15 - Film forming

[0454] This invention provides a method of manufacturing a film comprising steps of.

[0455] (1) preparing a base member;

[0456] (2) applying the composition of this invention above the base member; and 20 (3) polymerizing the (a) monomers in the composition.

[0457] The numbers in parentheses indicate the order of the steps. For example, when the steps (1), (2) and (3) are described, the order of the steps is as described above. Same to hereinafter, unless specifically described.

[0458] Here, in the present invention, the “above” includes the case where a film is formed on (direct contact with) a base member and the case where a film is formed above a base member via another layer. For example, a planarization film can be formed on a base member, and the composition of this invention can be applied on the planarization film.

[0459] 30

[0460] In general terms the present application also relates to an electronic device, preferably an organic electronic device, comprising a base member, and a Foreignfiling text P24-225

[0461] - 43 -

[0462] film, which may be produced in accordance with the present method as described herein.

[0463] Said base member is not particularly limited and may, in principle, be any 5 member (for example, a substrate or a device or device component, all of which are described in the following) whereupon a film may be deposited. Without wishing to be bound by theory, this film is believed to contribute to protecting the underlying base member from water, oxygen, dust, or any other materials harmful to the underlying base member.

[0464] The base member is preferably an electronic device or a component of an electronic device, and more preferably an organic electronic device or a component of an organic electronic devices.

[0465] Examples of such base members may be selected from the group of 15 electronic devices consisting of light emitting diodes, photovoltaic cells, photodetector cells, semiconductor devices, and thin film transistors, all of which may be organic, inorganic or hybrid.

[0466] Generally, such electronic device comprises, preferably in sequence, a first electrode, a functional layer, and a second electrode. The functional layer 20 may, for example, be selected from the group consisting of light emitting layer, semiconductor layer, and photoactive layer.

[0467] Depending upon the architecture of the resulting electronic device, the film may be on the side of (but not necessarily directly adhered thereto) the first electrode or the second electrode.

[0468] The substrate, whether as part of a base member or in itself constituting the base member, is not particularly limited. Suitable substrates are preferably inert under use conditions. Such substrates may, for example, be flexible. Preferred examples of suitable substrate materials may be selected from 30 polymers, glass, metals and any blend of any of these, including for example blends of more than one polymer or metal. Preferred polymeric materials include but are not limited to alkyd resins, allyl esters, benzocyclobutenes, Foreignfiling text P24-225

[0469] - 44 -

[0470] butadiene-styrene, cellulose, cellulose acetate, epoxide, epoxy polymers, ethylene-chlorotrifluoro ethylene copolymers, ethylene-tetra-fluoroethylene copolymers, fiber glass enhanced polymers, fluorocarbon polymers, hexafluoropropylenevinylidene-fluoride copolymer, high density polyethylene, 5 parylene, polyamide, polyimide, polyaramid, polysiloxanes (e.g.

[0471] polydimethylsiloxane), polyethersulphone, polyethylene, polyethylenenaphthalate, polyethyleneterephthalate, polyketone, polymethylmethacrylate, polypropylene, polystyrene, polysulphone, polytetrafluoroethylene, polyurethanes, polyvinylchloride, polycycloolefin, silicone rubbers, silicones, and maleimide-type resins. Of these polyethyleneterephthalate, polyimide, polycycloolefin and polyethylenenaphthalate materials are more preferred. Additionally, for some embodiments of the present invention the substrate can be any suitable material, for example a polymeric material, metal or glass material coated 15 with one or more of the above listed materials or coated with one or more metal, such as for example titanium. It will be understood that in forming such a substrate, methods such as extruding, stretching, rubbing or photochemical techniques can be employed to provide a homogeneous surface for device fabrication. Alternatively, the substrate can be a polymeric material, metal or 20 glass coated with one or more of the above polymeric materials.

[0472] In the step (2) of this invention, the measure of “applying” the composition is preferably selected from the group consisting of deposition, dip coating, spin coating, inkjet printing, nozzle printing, letter-press printing, screen printing, gravure printing, doctor blade coating, roller printing, reverse-roller printing, offset lithography printing, dry offset lithography printing, flexographic printing, web printing, spray coating, curtain coating, brush coating, slot dye coating and pad printing (more preferably deposition, spin coating, ink jet printing or nozzle printing; further preferably spin coating, and inkjet printing; 30 further more preferably inkjet printing).

[0473] In the step (3) of this invention, the (a) monomers are polymerized to be a Foreignfiling text P24-225

[0474] - 45 -

[0475] film. The measure of “polymerizing” in the step (3) is performed by irradiation and / or heat (preferably irradiation).

[0476] As above irradiation, wavelength having 260-430 nm peak top wavelength can be preferably used (more preferably 350-410 nm peak top; further 5 preferably 380-400 nm peak top). UV irradiation is one preferable embodiment of such irradiation. The atmosphere of such irradiation can be selected from the known conditions such like that air atmosphere, nitrogen, and mixture of them. Temperature can be controlled as know conditions such like that 20-27 °C (preferably 25-27 °C).

[0477] As mentioned above, heat treatment by applying increased temperature to the composition above the base member is one embodiment of this invention.

[0478] 50-150 °C (preferably 70-120 °C) is one embodiment of such condition. 10-180 minutes (preferably 10-60 minutes) is one embodiment of such condition. The atmosphere of such heat treatment can be selected from the known 15 conditions such like that air atmosphere, nitrogen, and mixture of them.

[0479] Temperature can be controlled as know conditions such like that 20-27 °C (preferably 25-27 °C).

[0480] By using the composition of this invention, it’s possible to form a substantially 20 transparent film when exposed to suitable radiation. The polymer manufactured by methods described in this specification can be the substantially transparent film. The suitable radiation source can be a natural light, or artificial light (e.g., LED light).

[0481] The substantially transparent film can have an average transmission of preferably 80-99.9% (more preferably 90-99.9%; further preferably 95- 99.9%; furthermore preferably 97-99.9%) of the 450-800 nm wavelength light. It is preferable embodiment of this invention that is most of the visible light is transmitted through the film. Accordingly, as one embodiment of this invention, such film can have preferably 90-100% (more preferably 90- 30 99.9%; further preferably 95-99.9%) of visible light) of visible light transmission. The visible light can be preferably 360-830 nm (more preferably 400-830 nm; further preferably 400-760 nm). Foreignfiling text P24-225

[0482] - 46 -

[0483] The substantially transparent film can have an average transmission of 5- 60% as of the range of 250-450 nm wavelength light. Without wishing to be bounded by theory, the substantially transparent film can be incorporated in 5 the light emitting device which can exhibit good visibility.

[0484] It is preferable embodiment of this invention that the substantially transparent film has an average transmission of 5-25% as of the range of 310-360 nm wavelength light. It is preferable embodiment of this invention that the substantially transparent film has an average transmission of 1-20% as of the range of 370-410 nm wavelength light.

[0485] Transmission amount can be measured and evaluated by known methods.

[0486] It is one embodiment of this invention that the manufactured film can have a permittivity of preferably 3 or less (more preferably 2.6 or less; further 15 preferably 2.5 or less). A permittivity of the film can be evaluated by known methods. Without wishing to be bound by theory, the film having above permittivity can exhibit characters as encapsulation layer or insulation layer.

[0487] As one embodiment of this invention, the polymer of this invention is formed 20 having a weight average molecular weight (Mw) from 5,000 to 500,000 (more preferably 10,000 to 400,000; further preferably 20,000 to 250,000). In the present invention, Mwand Mncan be measured by the gel permeation chromatography (GPC). In this measurement, it is a preferable example to use a GPC column at 40°C, an eluent tetrahydrofuran at 0.6 mL / min and mono-dispersed polystyrene as a standard.

[0488] This invention provides a manufacturing of film, comprises above mentioned steps of (1), (2), (3) and;

[0489] (4) applying one or more additional layers above the film.

[0490] 30

[0491] It is one embodiment of the invention that the additional layers are preferably selected from the group consisting of organic layers, inorganic layers, and Foreignfiling text P24-225

[0492] - 47 -

[0493] hybrid layers (more preferably selected from the group consisting of an inorganic layer comprising a material selected from the group consisting of silicon oxide, silicon nitride, silicon oxynitride, aluminium oxynitride, magnesium oxide, aluminium oxide, aluminium nitride, titanium oxide, 5 titanium nitride, tantalum oxide, tantalum nitride, hafnium oxide, hafnium nitride, zirconium oxide, zirconium nitride, cerium oxide, cerium nitride, indium oxide, tin oxide, tin nitride and any blend of any of these). Further preferably such additional layers constitute of a touch panel.

[0494] - Device manufacturing

[0495] Without wishing to be bound by theory, film manufactured by the above- mentioned invention can have good property of transparency or flexibility. Including such film in an electronic device is advantageous. Also setting such film above a base member (preferably the base member is an electronic 15 device) of this invention is advantageous.

[0496] This invention provides a method of manufacturing an electronic device comprising a method of manufacturing above mentioned film.

[0497] It is one embodiment of this invention that the electronic device is preferably 20 a light emitting device (more preferably an organic light emitting device).

[0498] Preferably the light emitting device comprises in sequence a first electrode (more preferably anode), a light emitting layer, and a second electrode (more preferably cathode). Preferably the organic light emitting device comprises in sequence a first electrode (more preferably anode), a hole transport layer, a light emitting layer, an electron transport layer, and the second electrode (more preferably cathode).

[0499] For these further processing, known methods can be applied. For example, after forming the base member of this invention, if necessary, the base 30 member is cut into chips, which are connected to a lead frame and packaged with resin. As another embodiment, the film according to this invention can constitute a layer of fabrication layers in a device (e.g., Lighting device). Foreignfiling text P24-225

[0500] -48 -

[0501] This invention also provides an electronic device manufactured by the method described above.

[0502] In another aspect, the present invention also relates to an electronic device 5 comprising at least one functional medium configured to modulate a light or configured to emit light; and the film. Said functional medium may be OLED or LCD, preferably it is OLED.

[0503] The invention will now be described in more detail by reference to the following examples, which area illustrative only and do not limit the scope of the invention.

[0504] Examples

[0505] The following abbreviations have been used hereinbefore and hereafter in 15 describing some of the compounds, instruments and / or methods employed to illustrate certain of the embodiments of this invention:

[0506] DecNB: 5-decylbicyclo[2.2.1 ]hept-2-ene

[0507] TD: tetracyclododecene

[0508] 20 PETD:2-phenethyl-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8- dimethanonaphthalene

[0509] CL1: 1,1,3,3,-Tetramethyl-1,3-bis-[2-(5-norbornen-2-yl)-ethyl]-disiloxan Ru-1:[1,3-bis(2,6-diisopropylphenyl)-2-imidazolidinylidene]{2-[(E)-({2- [methylthio-KS]phenyl}imino-KN)methyl]phenoxido-KO}[2-(oxido- KO)benzylidene-KC]ruthenium(ll)

[0510] ITX: lsopropyl-9H-thioxanthen-9-one

[0511] CPTX: 1 -chloro-4-propoxy-9H-thioxanthen-9-one

[0512] Example 1: Reference film sample 1 preparation

[0513] 30 In a glass bottle, ITX (0.02 wt %), palladium(hexafluoroacetylacetonate)2 tri- isopropylphosphine (0.06 wt %), lodonium, diphenyl-, 4,4’-di-C10-13-alkyl derivs, tetrakis(2,3,4,5,6-pentafluorophenyl)borates (0.58 wt %) and Bis-(1 - Foreignfiling text P24-225

[0514] - 49 -

[0515] octyloxy-2,2,6,6-tetramethyl-4-piperidinyl)sebacate (0.02 wt %) are dissolved in DecNB (99.32 wt %) without solvent to form a clear composition. The composition is checked optically for full dissolution and filtered. Then the composition is spin coated under nitrogen atmosphere on pre-cleaned 5 Quartz substrates, to be wet films. The wet film is illuminated with UV light of 395 nm under nitrogen atmosphere to cure the film, the dose applied was in general between 0.5 and 5 J / cm2The spin coating parameters are optimized to obtain 8 μm film thickness. The film thickness is determined by profilometry after curing the film as the height difference between the film surface and the substrate surface (after scratching with a scalpel) with a stylus-type profilometer. Then reference film sample 1 is obtained.

[0516] Example 2: Working film sample 1 preparation

[0517] Working film sample 1 is obtained in the same manner as described in 15 example 1 above, except for that an extra 1 wt % of DISPERBYK®-322 is added to the composition (the respective additive was added in a ratio 99:1) so that the final mixing ratios of the materials are different to example 1.

[0518] Example 3: Working film sample 2, comparative film samples 1-2 20 preparation

[0519] Working film sample 2 and comparative film samples 1-2 are obtained in the same manner as described in example 2 except for that different silicone- based surfactants instead of DISPERBYK®-322 are used, as shown in table 1 below.

[0520] Table 1

[0521] Examples Surfactant Dissolving in Wetting Curing of additive formulation property formulation

[0522] 30

[0523] Reference none - De-wetting Yes film sample 1

[0524]

[0525] Foreignfiling text P24-225

[0526] - 50 -

[0527] Working film BYK ® -322 Yes Improved Yes sample 1 (1 wt %)

[0528] Working film BYK ® -323 Yes Improved Yes sample 2 (1 wt %)

[0529] 5

[0530] Comparative BYK ® -331 Yes Strong deImpeded film sample 1 (1 wt %) wetting

[0531] Comparative BYK ® -307 Yes Slight deImpeded film sample 2 (1 wt %) wetting

[0532]

[0533] As can be seen in table 1, without silicone-based surfactants, the film experiences de-wetting. For working film samples 1-2, the silicone-based surfactants added are both aralkyl modified silicones, the de-wetting is improved. For comparative film samples 1 -2, polyether modified silicones are added as the silicone-based surfactants, de-wetting effects are observed 15

[0534] here.

[0535] Example 4: Reference film sample 2 preparation

[0536] In a glass bottle, CPTX (0.10 wt %) and Ru-1 (0.05 wt %) are dissolved in TD (99.85 wt %) without solvent to form a clear composition. The composition 20

[0537] is checked optically for full dissolution and filtered. Then the composition is spin coated under nitrogen atmosphere on pre-cleaned Quartz substrates, to be wet films. The wet film is illuminated with UV light of 395 nm under nitrogen atmosphere to cure the film, the dose applied was in general between 0.5 and 5 J / cm2. The spin coating parameters are optimized to obtain 8 μm film thickness. The film thickness is determined by profilometry after curing the film as the height difference between the film surface and the substrate surface (after scratching with a scalpel) with a stylus-type profilometer. Then reference film sample 2 is obtained.

[0538] 30

[0539] Example 5: Working film sample 3 preparation

[0540] Working film sample 3 is obtained in the same manner as described in Foreignfiling text P24-225

[0541] - 51 -

[0542] example 4 above, except for that an extra 1 wt % of DISPERBYK®-323 is added to the composition (the respective additive was added in a ratio 99:1) so that the final mixing ratios of the materials are different to example 4.

[0543] 5 Example 6: Working film samples 4-6, comparative film sample 3 preparation

[0544] Working film samples 4-6 and comparative film sample 3 are obtained in the same manner as described in example 5 except for that different surfactants instead of DISPERBYK®-323 are used, as shown in table 2 below.

[0545] Table 2

[0546] Examples Surfactant Dissolving in Wetting Curing of additive formulation property formulation Reference film none - De-wetting Yes sample 2

[0547] Working film BYK®-323 (1 Yes Improved Yes sample 3 wt %)

[0548] Working film BYK®-322 (1 Yes Improved Yes sample 4 wt %)

[0549] Working film BYK®-331 (1 Yes Improved Yes sample 5 wt %)

[0550] Working film BYK®-307 (1 Yes Improved Yes sample 6 wt %)

[0551] Comparative DISPERBYK®- Yes Strong deImpeded film sample 3 170(1 wt %) wetting

[0552]

[0553] As can be seen in table 2, without silicone-based surfactants, the film experiences de-wetting. For working film samples 3-4, the silicone-based surfactants added are aralkyl modified silicones, the de-wetting is improved.

[0554] 30 And for working film samples 5-6, the silicone-based surfactants added are polyether modified silicones, the de-wetting is improved. For comparative film sample 3, DISPERBYK®-170 is added. DISPERBYK®-170 does not contain Foreignfiling text P24-225

[0555] - 52 -

[0556] any silicone, it is a block copolymer wetting and dispersing additive, when it is added, strong de-wetting is observed.

[0557] Example 7: Working film sample 7 preparation

[0558] 5 In a glass bottle, CPTX (0.10 wt %) and Ru-1 (0.03 wt %) are dissolved in DecNB (59.92 wt %), CL1 (29.96 wt %) and PETD (9.99 wt %) without solvent to form a clear composition. Then DISPERBYK®-323 was added to this composition as an additive in a ratio 99:1 (1% of additive in the final composition). The composition is checked optically for full dissolution and filtered. Then the composition is spin coated under nitrogen atmosphere on pre-cleaned Quartz substrates, to be wet films. The wet film is illuminated with UV light of 395 nm under nitrogen atmosphere to cure the film, the dose applied was in general between 0.5 and 5 J / cm2. The spin coating parameters are optimized to obtain 8 μm film thickness. The film thickness is 15 determined by profilometry after curing the film as the height difference between the film surface and the substrate surface (after scratching with a scalpel) with a stylus-type profilometer. Then working film sample 7 is obtained. The conditions of working film sample 7 is shown in table 3 below.

[0559] 20 Table 3

[0560] Example Surfactant Wetting Curing of additive property formulation Working film BYK®-323 Improved Yes

[0561] sample 7 (1 wt %)

[0562]

[0563] Working film sample 7 which has an aralkyl modified silicone DISPERBYK® -323 added as an additive experiences good wetting and shape retention on the surface after printing.

[0564] 30

Claims

Foreignfiling text P24-225- 53 -Claims1. A composition comprising at least:a) one or more chemical compound of formula (I):5whereinm is an integer 0, 1 or 2;Ri, R2, R3 and R4 are the same or different and each independently selected from the group consisting of hydrogen, halogen, methyl, ethyl, linear or branched (C3-Cie)alkyl, perfluoro(Ci-Ci2)alkyl,15 hydroxy(Ci-Cie)alkyl, (C3-Ci2)cycloalkyl, (C6-Ci2)bicycloalkyl,(C7-Ci4)tricycloalkyl, (Ce-Cio)aryl, (C6-Cio)aryl(Ci-Ce)alkyl, perfluoro(Ce-Cio)aryl, perfluoro(C6-Cio)aryl(Ci-C6)alkyl, tri(Ci-Ce)alkoxysilyl and a group of formula (A):20 -Z1-Aryl (A)whereinZ1is a bond or a group selected from the group consisting of:(CR5R6)a, O(CR5R6)a, (CR5R6)aO, (CR5R6)a-O-(CR5R6)b,(CR5R6)a-O-(SiR5R6)b, (CR5R6)a-(CO)O-(CR5R6)b,(CR5R6)a-O(CO)-(CR5R6)b, (CR5R6)a-(CO)-(CR5R6)b, where a and b are integers which may be the same or different and each independently is 1 to 12;R5and R6are the same or different and each independently selected from 30 the group consisting of hydrogen, methyl, ethyl, linear or branched (C3- C6)alkyl, hydroxy, methoxy, ethoxy, linear or branched (C3-C6)alkyloxy,Foreignfiling text P24-225- 54 -acetoxy, (C2-C6)acyl, hydroxymethyl, hydroxyethyl, linear or branched hydroxy(C3-Ce)alkyl, phenyl and phenoxy;Aryl is phenyl or phenyl substituted with one or more of groups selected from the group consisting of methyl, ethyl, linear or branched (C3-Ce)alkyl, 5 hydroxy, methoxy, ethoxy, linear or branched (C3-Ce)alkyloxy, acetoxy, (C2- Ce)acyl, hydroxymethyl, hydroxyethyl, linear or branched hydroxy(C3- Ce)alkyl, phenyl and phenoxy;b) a catalyst, preferably a transition metal containing catalyst compound;(c) a photoactive compound represented by formula (III):15whereinY is halogen or hydrogen; andR30 and R31 are the same or different and independently of each other selected from the group consisting of hydrogen, methyl, ethyl, linear or 20branched (C3-Ci2)alkyl, (C3-Ci2)cycloalkyl, (C6-Ci2)bicycloalkyl,(C7-Ci4)tricycloalkyl, (Ce-Cio)aryl, (C6-Cio)aryl(Ci-C3)alkyl, (Ci-Ci2)alkoxy, (C3-Ci2)cycloalkoxy, (C6-Ci2)bicycloalkoxy, (C7-Ci4)tricycloalkoxy,(C6-Cio)aryloxy(Ci-C3)alkyl and (Ce-Cio)aryloxy; and(d) a silicone-based surfactant.

2. The composition according to claim 1, wherein the content of the (d) silicone-based surfactant is in the range from 0.0001 to 2.0 wt % based on the total amount of the composition.30Foreignfiling text P24-2253. Composition of claim 1 or 2, wherein said (d) silicone-based surfactant has a siloxane bond represented by following chemical formula (VI),■ CH35 (CH3)3Si — o - Si - O - SiSi(CH3)3R(VI)X(VI)whereinR(VI) is linear or branched (Ci-Cso)alkyl;X(VI) is an integer from 1-100;said (d) silicone-based surfactant is an aralkyl modified silicone represented by following chemical formula (IV),CH" CH 33(CH3)3Si — o - Si - o -Si — O Si(CH3)3R(IV)-2-> x(l V)(IV)whereinR(IV)-1 is an aralkyl group. Aryl is phenyl or phenyl substituted with one or more of groups selected from the group consisting of methyl, ethyl, linear or branched (C3-Ce)alkyl, hydroxy, methoxy, ethoxy, linear or branched (C3- Ce)alkyloxy, acetoxy, (C2-Ce)acyl, hydroxymethyl, hydroxyethyl, linear or branched hydroxy(C3-Ce)alkyl, phenyl and phenoxy;R(IV)-2 is linear or branched (Ci-Cso)alkyl;30m(IV) is an integer from 1-100;x(IV) is an integer from 1-100;Foreignfiling text P24-225y(IV) is an integer from 1-100;orsaid (d) silicone-based surfactant is a polyether modified silicone5 represented by following chemical formula (V),CH3CH3Si — O — Si(CH3)3(Qh2)m(V)L CH3oCH2CH— R,R(V)-2(V)whereinR(V)-1 and R(V)-2 are the same or different and each independently selected from, hydrogen and linear or branched (Ci-Cso)alkyl;m(V) is an integer from 1-100;n(V) is an integer from 1-100;x(IV) is an integer from 1-100;y(IV) is an integer from 1-100.

4. The composition of any one of preceding claims, wherein the monomer of formula (I) is selected from the group consisting of:305-(4-phenylbutyl)bicyclo[2.2.1 ]hept-2-ene;Foreignfiling text P24-22555-phenethylbicyclo[2.2.1 ]hept-2-ene (PENB);5-decylbicyclo[2.2.1 ]hept-2-ene (DecNB);5-(benzyloxy)bicyclo[2.2.1 ]hept-2-ene;5-(2-([1, 1 '-biphenyl]-4-yloxy)ethyl)bicyclo[2.2.1 ]hept-2-ene;5-(2-([1, 1 '-biphenyl]-2-yloxy)ethyl)bicyclo[2.2.1 ]hept-2-ene (NBEtO-2- PhPh);30Foreignfiling text P24-2255-butylbicyclo[2.2.1 ]hept-2-ene (BuNB);55-hexylbicyclo[2.2.1 ]hept-2-ene (HexylNB);5-octylbicyclo[2.2.1 ]hept-2-ene (OctNB);5-decylbicyclo[2.2.1 ]hept-2-ene (DecNB);5-ethylidenebicyclo[2.2.1 ]hept-2-ene;2-ethylidene-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene;3a,4,4a,5,8,8a,9,9a-octahydro-1 H-4, 9:5,8- dimethanocyclopenta[b]naphthalene (one of trimers of cyclopentadiene, TCPD1, also known as CPD3);30Foreignfiling text P24-22555-norbornenylmethyleugenyl acetate (EuAcNB);5-norbornenylmethyleugenol (EuOHNB);(bicyclo[2.2.1 ]hept-5-en-2-ylmethoxy)(methyl)diphenylsilane (NBCH2OSiMePh2);(bicyclo[2.2.1 ]hept-5-en-2-ylmethoxy)(ethyl)diphenylsilane;30Foreignfiling text P24-2255(bicyclo[2.2.1]hept-5-en-2-ylmethoxy)(ethyl)(methyl)(phenyl)silane;(bicyclo[2.2.1 ]hept-5-en-2-ylmethoxy)dimethyl(phenyl)silane;Si(OCH3)3bicyclo[2.2.1 ]hept-5-en-2-yltrimethoxysilane (TMSNB);bicyclo[2.2.1]hept-5-en-2-yltriethoxysilane (NBSi(OC2H5)3);bicyclo[2.2.1 ]hept-5-en-2-yl(tert-butoxy)dimethoxysilane;Si(OMe)3(2-(bicyclo[2.2.1 ]hept-5-en-2-yl)ethyl)trimethoxysilane;30Foreignfiling text P24-225- 61 -OHOH5 NB(MeOH)2;tetracyclododecene (TD);2-phenyl-tetracyclododecene (PhTD);2-benzyl-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene;2-phenethyl-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene (PETD);30Foreignfiling text P24-2252-butyl-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene 5 (ButylTD);2-hexyl-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene (HexylTD);2-octyl-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene (OctylTD);2-decyl-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene (DecylTD);2-cyclohexyl-tetracyclododecene (CyclohexylTD);2- cyclohexylmethyl-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8- dimethanonaphthalene;30Foreignfiling text P24-2255 2- cyclohexylethyl-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8- dimethanonaphthalene;(1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalen-2-yl)methyl acetate (TDMeOAc);tetracyclododecadiene (TDD) ; and1, 1,3,3,-Tetramethyl-1,3-bis-[2-(5-norbornen-2-yl)-ethyl]-disiloxan (CL1 ).

5. The composition of any one of preceding claims, wherein said catalyst is transition metal containing catalyst compound, preferably the transition metal containing catalyst compound is an organo-ruthenium compound represented by formula (II):30Foreignfiling text P24-2255whereinc and d are integers from 0 to 5;Z is oxygen or sulfur;R7 is selected from the group consisting of hydrogen, (C1-C20)alkyl,(C2-C20)alkenyl, (C2-C20)alkynyl and (C6-C10)aryl; andRs, R9, R10 and Rn are the same or different and each independently 15 selected from the group consisting of hydrogen, halogen, (Ci -Cis)alkyl, (C1- Cis)alkoxy, (Ci-Ci6)perfluoroalkyl, (C3-C7)cycloalkyl, (C2-Cis)alkenyl, (Ce- Ci4)aryl, (C6-Ci4)perfluoroaryl,(C3-C12)heterocyclyl, -OR16, -NO2, -COOH, -COOR16, -CONR16R17, -SO2NR16R17, -SO2R16, -CHO, -COR16,20 wherein R16 and R17 are the same or different and each independently selected from the group consisting of (C1-C6)alkyl, (C1-C6)perfluoroalkyl, (C6-C14)aryl, (C6-C14)perfluoroaryl; or whereintwo or more of Rs, R9, R10 and R11 taken together with the carbon atoms to which they are attached to form a substituted or unsubstituted, fused (C4-Cs)carbocyclic ring, or a substituted or unsubstituted, fused aromatic ring;each R12, R13 and R14 may be the same or different and independently of the other selected from the group consisting of hydrogen, halogen, (C1- Cis)alkyl, (Ci-Cis)alkoxy, (Ci-Ci6)perfluoroalkyl, (C3-C7)cycloalkyl, (C2- 30 Cis)alkenyl, (Cs-Ci4)aryl, (C6-Ci4)perfluoroaryl,(C3-Ci2)heterocyclyl, -OR16, -NO2, -COOH, -COOR16, -CONR16R17, -SO2NR 16R17, -SO2R16, -CHO, -COR, wherein R and R17 are the same orForeignfiling text P24-225different and each independently selected from the group consisting of (Ci- Ce)alkyl, (Ci-C6)perfluoroalkyl, (Ce-Ci4)aryl, (Ce-Ci4)perfluoroaryl;R15 is selected from the group consisting of (Ci -Cie)alkyl,(Ci-Ci6)perfluoroalkyl, (C3-Ci6)cycloalkyl, (Ce-Ci4)aryl, (Ce-Ci4)perfluoroaryl 5 and (C3-Ci2)heterocyclyl;Ar1 and Ar2 are the same or different and each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl and substituted or unsubstituted naphthyl, wherein each of said substituents are independently selected from the group consisting of methyl, ethyl and linear or branched (C3-Ce)alkyl.

6. The composition of any one of preceding claims, wherein said catalyst is a multi-component catalyst containing a group 10 transition metal complex procatalyst compound with a cocatalyst or activator.

157. The composition of any one of preceding claims, wherein said catalyst is an organo-ruthenium compound represented by formula (II) selected from the group consisting of:20[1,3-Bis(2,6-diisopropylphenyl)-2-imidazolidinylidene]{2-[(E)-({2-[methylthio- KS]phenyl}imino-KN)methyl]phenoxido-KO}[2-(oxido-KO)benzylidene- 30 KC]ruthenium(ll) (Ru-1);Foreignfiling text P24-2255[1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]{2-[(E)-({2- [isopropylthio-KS]phenyl}imino-KN)methyl]phenoxido-KO}[2-(oxido- KO)benzylidene-KC]ruthenium(ll);[1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]{2-[(E)-({2- [cyclohexylthio-KS]phenyl}imino-KN)methyl]phenoxido-KO}[2-(oxido- KO)benzylidene-KC]ruthenium(ll); and30Foreignfiling text P24-225- 67 -5[1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]{2-[(E)-({2-[methylthio- KS]phenyl}imino-KN)methyl]phenoxido-KO}[2-(oxido-KO)benzylidene- KC]ruthenium(ll).

8. The composition of any one of preceding claims, wherein said catalyst is 15a multi-component catalyst containing a group 10 transition metal complex procatalyst compound with a cocatalyst or activator, group 10 metal of said group 10 transition metal complex procatalyst compound is selected from nickel, palladium, and platinum, and with palladium being the most preferred metal, and said cocatalyst or activator is selected from sulfonium 20salt-type photo-acid generators, iodonium salt-type photo-acid generators, non-ionic photo-acid generators and other photo-acid generators.

9. The composition of any one of preceding claims, wherein the compound of formula (III) is selected from the group consisting of:301-chloro-4-methoxy-9H-thioxanthen-9-one;Foreignfiling text P24-225- 68 -51-chloro-4-ethoxy-9H-thioxanthen-9-one;1-chloro-4-propoxy-9H-thioxanthen-9-one;1-chloro-2-propoxy-9H-thioxanthen-9-one;1-chloro-2-ethoxy-9H-thioxanthen-9-one;1-chloro-2-methoxy-9H-thioxanthen-9-one; 30Foreignfiling text P24-22551-chloro-4-methyl-9H-thioxanthen-9-one;101-chloro-4-ethyl-9H-thioxanthen-9-one;1-bromo-4-propoxy-9H-thioxanthen-9-one 201 -chloro-4-phenoxy-9H-thioxanthen-9-one; and30 Isopropyl-9H-thioxanthen-9-one.Foreignfiling text P24-225- 70 -10. The composition of any one of preceding claims, wherein when catalyst is an organo-ruthenium compound, Y in photoactive compound is halogen, silicone-based surfactant is an aralkyl modified silicone or a polyether modified silicone, more preferably an aralkyl modified silicone.

511. The composition of any one of preceding claims, wherein when catalyst is a multi-component catalyst containing a group 10 transition metal complex procatalyst compound with a cocatalyst or activator, Y in photoactive compound is hydrogen, silicone-based surfactant is an aralkyl modified silicone.

12. The composition of any one of preceding claims, wherein the content of the (a) monomer is 80-99.99 wt % based on the composition; preferably the content of the (b) catalyst is 0.0001-1.5 wt % based on the 15 total amount of the composition;preferably the content of the (c) a photoactive compound is 0.0001-1.0 wt % based on the total amount of the composition.

13. The composition of any one of preceding claims, further comprises a 20 stabilizer and / or a crosslinker.

14. A method for preparing a composition of any one of the preceding claims, comprising a step of mixing the composition comprising at least (a) chemical compound of formula (I), (b) catalyst, (c) photoactive compound represented by formula (III) and (d) silicone-based surfactant.

15. A method of manufacturing a film comprising steps of;(1) preparing a base member;(2) applying the composition according to any one of the claims 1 to 13 30 above the base member; and(3) polymerizing the (a) monomers in the composition.Foreignfiling text P24-225- 71 - 16. A film obtained or obtainable by the method of claim 15.

17. An electronic device comprising the film of claim 16. 5152030

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