Composition for inkjet adaptive planarization

Abstract

The present invention relates to a curable composition, preferably being a photo-curable composition for inkjet adaptive planarization, comprising at least a 1st monomer and a polymerization initiator, the use of the composition for inkjet adaptive planarization, a method for preparing a cured layer and a cured layer prepared by the method.(Formula I)

Description

[0001] Foreignfiling text P25-161.docx

[0002] - 1 -

[0003] Composition for inkjet adaptive planarization

[0004] Field of the invention

[0005] The present invention relates to a curable composition, preferably being a photo-curable composition for inkjet adaptive planarization, the use of the 5

[0006] composition for inkjet adaptive planarization, a method for preparing a cured layer, a method for manufacturing a device and a cured layer.

[0007] Background Art

[0008] Inkjet Adaptive Planarization (IAP) is a process that can be used to planarize surfaces of substrates. For this purpose, liquid drops of a photo- curable composition are printed on the surface of a substrate. The drop pattern can be tailored to existing topographies. A superstrate, such as a quartz glass of extremely high planarity, is then brought into direct contact with the liquid to form a layer, which is then cured under the influence of UV-light. After removal of the superstrate, a planar surface is obtained, 15 which can be subjected to subsequent processing steps.

[0009] The photo-curable composition for IAP applications needs to fulfil several conditions: For the inkjet printing process, the composition needs to be liquid with a low viscosity of approximately < 50 cP at room temperature and a low vapor pressure. It furthermore needs to have a high storage 20 stability. For a high form stability of the printed layer, the solvent content of the composition needs to be low. The UV-curing of the composition needs to occur at sufficient photospeed to meet high throughput requirements and needs to result in a cured layer with a glass transition temperature of preferably > 120 °C and a low shrinkage of preferably < 7 %. The composition needs to comprise a suitable photoinitiator. The adhesion of the cured layer to the substrate needs to be high, whereas the adhesion to the superstrate needs to be sufficiently low to avoid separation defects during the removal of the superstrate. For the following baking step and the application of the next layer by a chemical vapor deposition (CVD) step, the cured layer needs to show low thermal weight loss, low thermal relaxation 30 shrinkage and low outgassing. Therefore, a high thermal stability of

[0010] > 350 °C is desired. For a high etch resistance of the cured layer, a highForeignfiling text P25-161.docx

[0011] -2 -

[0012] carbon content of the cured layer is desired, as the etch resistance is lower for layers with a high oxygen content.

[0013] State-of-the-art photo-curable compositions often contain a high content of acrylate monomers. However, it was found that the use of acrylate

[0014] 5

[0015] monomers results in reduced etching resistance. A higher carbon content of the cured film improves the etching resistance, which is crucial for the function as carbon-rich hard mask and the pattern etch transfer, but this higher carbon content cannot be achieved by the use of acrylate monomers. Furthermore, it is believed that the use of acrylates reduces the temperature stability of the cured film and leads higher degree of UV- induced shrinkage in photo-curable systems.

[0016] US 2022 / 0185914 A1 describes a photo-curable composition for inkjet adaptive planarization wherein the polymerizable material comprises at least one acrylate monomer and at least one multifunctional vinylbenzene.

[0017] 15

[0018] US 2023 / 0203210 A1 discloses a photo-curable composition comprising a polymerizable material and a photoinitiator, which can be adapted for use in inkjet adaptive planarization or nanoimprint lithography. The polymerizable compound is a biphenyl derivative, a diphenylether derivative or a diphenylmethylene derivative, each of which is substituted with one or more vinyl or 20 ethinyl groups.

[0019] US 2024 / 0191088 discloses a curable composition comprising a polymerizable compound, a photopolymerization initiator and a solvent wherein the polymerizable compound comprises at least one aromatic or heteroaromatic ring and at least four vinyl groups directly bonded to the aromatic or heteroaromatic ring. Examples for the polymerizable compound are tetravinylbenzene, tetravinylbiphenyl or tetravinylbenzophenone.

[0020] There are still technical problems with compositions for IAP for which improvement is desired, such as one or more of: improved thermal stability 30 after curing, preferably at > 350 °C; lower shrinkage after curing; improved etching resistance of a cured layer; improved planarization performance of a cured layer, namely over different pattern topographies of a substrate; lowForeignfiling text P25-161.docx

[0021] - 3 -

[0022] viscosity and / or low vapor pressure as a composition, preferably suitable for ink-jet printing; high storage stability of the composition; and providing a cured layer with mechanical durability.

[0023] Summary of the invention

[0024] 5

[0025] It has been surprisingly found that one or more of the above-described technical problems can be solved by a photo-curable composition as described in the following. In particular, the thermal stability after curing and the outgassing behavior are improved.

[0026] The object of the present invention is therefore a curable composition comprising a polymerization initiator and a compound of the following formula (1),

[0027]

[0028] Formula (1)

[0029] wherein the following applies to the symbols and indices used:

[0030] R1is the same or different at each occurrence and is H or CH3;

[0031] R2is the same or different at each occurrence and is an alkyl group having 1 to 10 carbon atoms which can be substituted by one or more F atoms or an aromatic ring system having 6 to 12 aromatic ring atoms which can be substituted by one or more F atoms and / or alkyl groups having 1 to 10 C atoms;

[0032] n is 1 , 2 or 3;

[0033] 30

[0034] m is 0, 1 , 2 or 3;Foreignfiling text P25-161.docx

[0035] - 4 -

[0036] o is 0, 1 , 2, 3 or 4, with the proviso that n + o < 5;

[0037] p is 0, 1 , 2, 3, 4 or 5, with the proviso that m + p < 5.

[0038] A further aspect of the present invention is a method for preparing a

[0039] 5

[0040] composition as described above comprising a step of mixing a compound according to formula (1) and a photoinitiator.

[0041] A further aspect of the present invention is the use of the composition in an inkjet adaptive planarization process.

[0042] A further aspect of the present invention is a method for preparing a cured layer, comprising the following steps in the following order:

[0043] (i) forming a layer of the composition of the invention on a substrate, for example by a process such as printing, in particular inkjet printing, spincoating or slit coating;

[0044] 15 (ii) optionally bringing the layer into contact with a template;

[0045] (iii) curing the composition by heat and / or by irradiation of the layer with light to form a cured layer;

[0046] (iv) optionally removing the template from the cured layer.

[0047] A further aspect of the present invention is a method for manufacturing a 20 device comprising the following steps:

[0048] (i) forming a cured film by the method of the present invention;

[0049] (ii) processing the substrate.

[0050] A further aspect of the present invention is a cured layer which is obtainable by the method described above and below. As further aspect is a stacked layer comprising a substrate and the cured layer.

[0051] A further aspect of the present invention is a compound represented by formula (1 ’),Foreignfiling text P25-161.docx

[0052] 5

[0053]

[0054] Formula (T)

[0055] wherein the following applies to the symbols and indices used:

[0056] R1is the same or different at each occurrence and is H or CH3;

[0057] R2is the same or different at each occurrence and is an alkyl group having 1 to 10 carbon atoms which can be substituted by one or more F atoms or an aromatic ring system having 6 to 12 aromatic ring atoms which can be substituted by one or more F atoms and / or alkyl groups having 15 1 to 10 C atoms;

[0058] n is 1 , 2 or 3;

[0059] m is 0, 1 , 2 or 3;

[0060] 20 with the proviso that n + m > 2;

[0061] o is 0, 1 , 2, 3 or 4, with the proviso that n + o < 5;

[0062] p is 0, 1 , 2, 3, 4 or 5, with the proviso that m + p < 5.

[0063] Detailed Description

[0064] Unless otherwise specified, all technical and scientific terms used herein have the same meanings as commonly understood by one of ordinary skill in the art to which this invention belongs. The materials, methods and examples are illustrative only and not intended to be limiting. Additionally, 30 the following definitions apply for the present invention.Foreignfiling text P25-161.docx

[0065] - 6 -

[0066] The use of the terms "a", "an", "the" and similar referents in the context of describing the disclosed and claimed subject matter and in the context of the following claims are to be construed to cover both the singular and the plural, unless otherwise indicated herein or clearly contradicted by context. Any reference to “one or more” or “at least one” includes “two or more” and “three 5 or more” and so on. The terms “comprising,” “having,” “including,” and “containing” are to be construed as open-ended terms ( / .e., meaning “including, but not limited to”) unless otherwise noted. The use of the term “comprising” or “including” includes the narrower language of “consisting essentially of” and “consisting of.” Recitation of ranges of values herein are merely intended to serve as a shorthand method of referring individually to each separate value falling within the range, unless otherwise indicated herein, and each separate value is incorporated into the specification as if it was individually recited herein. When a numerical range is indicated using “to” or it includes both endpoints. All methods described herein can be performed in any suitable order unless otherwise indicated herein or otherwise clearly contradicted by context. The use of any and all examples, or 15 exemplary language (e.g., “such as”) provided herein, is intended merely to better illuminate the disclosed and claimed subject matter and does not pose a limitation on the scope of the disclosed and claimed subject matter unless otherwise claimed. No language in the specification should be construed as indicating any non-claimed element as essential to the practice of the invention.

[0067] 20

[0068] All percentages of the components are weight percentages and are based on the total weight of the composition, i.e. 100%, unless otherwise indicated herein. When specific components of the composition are discussed in reference to weight percentage (or weight % or wt%) ranges including a zero lower limit, it is understood that such components may be present or absent and that in instances where such components are present, they may be present at concentrations as low as 0.001 wt%, based on the total weight of the composition. Moreover, when referring to the compositions described herein in terms of weight %, it is understood that in no event shall the wt% of all components, including non-essential components or impurities, add to more than 100 wt%. In compositions “consisting essentially of’ recited

[0069] 30 components, such components may add up to 100 wt% of the composition or may add up to less than 100 wt%. Where the components add up to less than 100 wt%, such composition may include some small amounts of a non-Foreignfiling text P25-161.docx

[0070] - 7 -

[0071] essential contaminants or impurities. For example, in one such embodiment, the composition can contain 1 wt% or less of impurities. Otherwise, if no non- essential component is present, it is understood that the composition of all essential constituent components will essentially add up to 100 wt%.

[0072] 5 The descriptions such as “Cx-y”, “Cx-Cy” and “Cx” mean the number of carbon atoms in a molecule or substituent. For example, C1-6 alkyl means an alkyl chain having 1 or more and 6 or less carbon atoms (methyl, ethyl, propyl, butyl, pentyl, hexyl). In the context of the present invention, the term "alkyl group" is used as a generic term for linear, branched or cyclic alkyl groups. A cyclic alkyl group in the context of this invention is understood to mean a monocyclic or bicyclic group. A linear alkyl group having 1 to 6 C atoms is methyl, ethyl, n-propyl , n-butyl, n-pentyl or n-hexyl. A branched alkyl group having 3 to 6 C atoms is, for example, iso-propyl, iso-butyl (2-methyl- prop-1 -yl), sec-butyl (2 -propyl), tert-butyl, sec-pentyl (2 -pentyl), 3-pentyl, 2- methyl-butyl, iso-pentyl (iso-amyl, 3-methyl-butyl), 3-methyl-but-2-yl, 2-methyl- 15 but-2-yl, neo-pentyl (2,2-dimethylpropyl), 2-hexyl or 3-hexyl. A cyclic alkyl group having 3 to 6 C atoms is, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopropyl, methylcylobutyl or methylcyclopentyl.

[0073] When a polymer has multiple types of repeating units, it may be any of an alternating copolymer, a random copolymer, a block copolymer, a graft 20 copolymer, or a mixture thereof.

[0074] In the following section, preferable compositions according to the present invention are described. As described above, the composition according to the present invention comprises at least one compound according to formula (1) and at least one polymerization initiator. The compound according to formula (1) is also referred to as monomer, as it is capable of undergoing a polymerization reaction during the curing process. As it comprises more than one reactive vinyl group, the polymerization reaction may result in a crosslinked polymer.

[0075] In a preferred embodiment, the composition of the invention is a photo- 30

[0076] curable composition and the polymerization initiator is a photoinitiator.Foreignfiling text P25-161.docx

[0077] - 8 -

[0078] The compound of formula (1) or the preferred embodiments can also be partially or fully deuterated.

[0079] In a preferred embodiment of the invention, at least one of the substituents R1in the central vinyl group, i.e. the vinyl group linked to both phenyl rings, 5

[0080] is H, and particularly preferred, both substituents R1in the central vinyl group are H. A preferred compound of formula (1) is therefore a compound of the following formula (2),

[0081]

[0082] Formula (2)

[0083] 15 where the symbols and indices have the same meanings as described above.

[0084] In a further preferred embodiment of the invention, n is 1 or 2 and m is 0, 1 or 2, with the proviso that n + m > 2. The following combinations of n and m are preferred:

[0085] 20 - n = 1 and m = 1 ;

[0086] - n = 2 and m = 0;

[0087] - n = 2 and m = 1 ;

[0088] - n = 2 and m = 2.

[0089] Particularly preferred are compounds with n = 1 and m = 1 or with n = 2 and m = 1.

[0090] It is furthermore preferred for n = 2 or m = 2 that the vinyl groups are not bound to adjacent carbon atoms of the phenyl ring. It is furthermore preferred that the vinyl groups R1-C(=CH2)- are not bound in an orthoposition to the central vinyl linking the two phenyl rings.

[0091] 30Foreignfiling text P25-161.docx

[0092] - 9 -

[0093] Preferred compounds of the formula (2) are the compounds of the following formulae (3), (4) and (5),

[0094] 5

[0095]

[0096] Formula (5)

[0097] wherein the symbols and indices have the same meanings as defined above and q and r are each independently 0 or 1.

[0098] In a further preferred embodiment of the invention, R2is the same or different at each occurrence and is selected from an alkyl group having 1 to 5 carbon atoms, particularly preferably a methyl group, or a phenyl group.

[0099] In a further preferred embodiment of the invention, o = 0, 1 or 2, particularly preferably 0 or 1 and most preferred 0, and p = 0, 1 or 2, particularly preferably 0 or 1 and most preferred 0.

[0100] Particularly preferred compounds of the formula (2) are therefore the compounds of the following formula (2a),

[0101] 30

[0102]

[0103] Foreignfiling text P25-161.docx

[0104] - 10 -

[0105] Formula (2a)

[0106] wherein the symbols and indices have the same meanings as defined above.

[0107] 5

[0108] Particularly preferred embodiments of the compounds of formulae (3), (4) and (5) are the compounds of the following formulae (3a), (4a) and (5a),

[0109] Formula (3a)

[0110]

[0111] Formula (5a)

[0112] wherein the symbols and indices have the same meanings as defined above and q and r are each independently 0 or 1.

[0113] In a further preferred embodiment of the invention, R1is H. Preferred compounds of the formula (2) are therefore the compounds of the following formula (2b),

[0114]

[0115] 30

[0116] Formula (2b)Foreignfiling text P25-161.docx

[0117] - 11 -

[0118] where the symbols and indices have the same meanings as described above.

[0119] Preferred compounds of the formulae (3), (4) and (5) are the compounds of the following formulae (3b), (4b) and (5b),

[0120] 5

[0121] Formula (4b)

[0122]

[0123] Formula (5b)

[0124] wherein the symbols and indices have the same meanings as defined above and q and r are each independently 0 or 1.

[0125] Particularly preferred are the compounds of the following formula (3c), (4c) and (5c),

[0126]

[0127] Formula (3c) Formula (4c)

[0128] 30Foreignfiling text P25-161.docx

[0129] - 12 -

[0130] 5

[0131]

[0132] Formula (5c)

[0133] wherein q and r are each independently 0 or 1.

[0134] The composition according to the present invention can comprise one compound of the formula (1 ) or the preferred embodiments or it can comprise more than one different compounds of the formula (1 ) or the preferred embodiments.

[0135] Preferred examples for the compound of formula (1 ) are the following compounds (A) to (F):

[0136] 30

[0137]

[0138] Foreignfiling text P25-161.docx

[0139] - 13 -

[0140] In a preferred embodiment of the present invention, the total amount of the compound of formula (1) or the preferred embodiments is in the range from 5 to 99 wt% based on the total amount of the composition, more preferably from 10 to 90 wt%, more preferably from 10 to 80 wt%, and most preferably 5

[0141] 20 to 50 wt%.

[0142] Preferably, the carbon content of the compound of formula (1) is at least 80%.

[0143] In a further embodiment of the present invention, the composition comprises at least one further compound, which as a polymerizable compound (monomer) and which is not embraced by the formula (1). The composition may optionally also contain a 3rdand / or a 4thmonomer or optionally further monomers. Said 3rdand / or 4thmonomers are different from each other, and it also differ from the 1stmonomer, i.e. the compound 15 of formula (1 ), and the 2ndmonomer.

[0144] In a preferred embodiment of the invention, the further monomer is a compound represented by the following formula (M1),

[0145] 20

[0146]

[0147] Formula (M1)

[0148] wherein the following applies to the symbols and indices:

[0149] X is the same or different at each occurrence and is selected from

[0150] -L2-CR4=C(R4)2or -L2-C=CR4;

[0151] L1is a single bond, O, C(=O), a linear alkylene group having 1 to 10 carbon atoms or a branched or cyclic alkylene group having 3 to 10 30 carbon atoms wherein the linear, branched or cyclic alkylene group can be substituted by one or more F atoms and wherein one or more non- adjacent C atoms of the alkylene group can be replaced by 0;Foreignfiling text P25-161.docx

[0152] - 14 -

[0153] L2is the same or different at each occurrence and is a single bond, a linear alkylene group having 1 to 10 carbon atoms or a branched or cyclic alkylene group having 3 to 10 carbon atoms wherein the linear, branched or cyclic alkylene group can be substituted by one or more F 5

[0154] atoms and wherein one or more non-adjacent C atoms of the alkylene group can be replaced by 0;

[0155] R3is the same or different at each occurrence and is a linear alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms wherein the linear, branched or cyclic alkyl group can be substituted by one or more F atoms, OH or COOH and wherein one or more non-adjacent C atoms of the alkyl group can be replaced by O;

[0156] R4is the same or different at each occurrence and is H, a linear alkyl 15 group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms; herein the linear, branched or cyclic alkyl group can be substituted by one or more F atoms, OH or COOH and wherein one or more non-adjacent C atoms of the alkyl group can be replaced by 0

[0157] 20 w is 0 or 1 , where for w = 0 either H or a group X or a group R3is bound instead of L1;

[0158] s is 1 , 2, 3 or 4;

[0159] t is 0, 1, 2, 3 or 4;

[0160] u, v is the same or different at each occurrence and is 0, 1 , 2, 3 or 4, with the proviso that s + u + w < 6 and v + t < 5.

[0161] The compound of formula (M1) can also be partially or fully deuterated. 30

[0162] Preferred compounds of the formula (M1 ) are compounds, for which the following applies to the symbols and indices:Foreignfiling text P25-161.docx

[0163] - 15 -

[0164] X is the same or different at each occurrence and is a group of formula -L2-CR4=C(R4)2;

[0165] L1is a single bond, a linear alkylene group having 1 to 5 carbon atoms or 5

[0166] a branched alkylene group having 3 to 5 carbon atoms; and particularly preferably a single bond, methylene or ethylene;

[0167] L2is a single bond, a linear alkylene group having 1 to 5 carbon atoms or a branched alkylene group having 3 to 5 carbon atoms; and particularly preferably a single bond, methylene or ethylene;

[0168] R3is the same or different at each occurrence and is a linear alkyl group having 1 to 5 carbon atoms or a branched or cyclic alkyl group having 3 to 5 carbon atoms; preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, i-butyl or t-butyl, and particularly preferably methyl; 15

[0169] R4is the same or different at each occurrence and is H, a linear alkyl group having 1 to 5 carbon atoms or a branched alkyl group having 3 to 5 carbon atoms; and more preferably H or methyl and most preferably H;

[0170] 20 w is 1 ;

[0171] s is 1 , 2 or 3, preferably 1 or 2;

[0172] t is 0, 1 , 2 or 3, preferably 0, 1 or 2 and more preferably 1 or 2;

[0173] u, v is the same or different at each occurrence and is 0, 1 or 2, preferably 0 or 1 and more preferably 0.

[0174] By adding the 2ndmonomer, i.e. the compound of formula (M1 ) in addition to the 1stmonomer, i.e. the compound of formula (1), and by controlling the 30 mixing ratio, the viscosity, crosslinking property and / or vapor pressure of the composition and / or the thermal stability, shrinkage after curing, etchingForeignfiling text P25-161.docx

[0175] - 16 -

[0176] resistance and / or planarization performance of the cured layer can be controlled. / X

[0177] As another embodiment of the present invention, the amount of the 2ndmonomer, i.e. preferably the compound of formula (M1), based on the total 5

[0178] amount of polymerizable compounds in the compositi ( / on is in the range from 10 to 90 wt%, preferably 20 to 80 wt%, more preferably 30 to 70 wt%.

[0179] As a preferred embodiment of the present invention, the sum amount of the 1stmonomer, i.e. the compound of formula (1 ), and the 2ndmonomer, i.e. preferably the compound of formula (M1 ), based on the total amount of the composition is in the range from 10 to 99.9 wt%, preferably from 50 to 99.9 wt% and most preferably from 80 to 99 wt%.

[0180] Examples for suitable monomers of the formula (M1 ) are shown in the following table.

[0181] / j

[0182] \ / _ ^2^ _ I occ )

[0183] p r

[0184] 30 ^onor

[0185]

[0186] Foreignfiling text P25-161 .docx

[0187] - 17 -

[0188] 1 x 'X^YY fXXX

[0189] Y vv ^ ^

[0190] Q X33xX o

[0191] -'

[0192] 1 1'~Y^

[0193] LA^ ^x3

[0194] 5 ( / YY16

[0195] / = o

[0196] ^ c 1!i

[0197] j X

[0198] F-C <Y

[0199] ,. 1 ^ 1 II _ I i I V I._ ux ~ S^^s ” \ _x'A^tKAA, % jf,OM\ 3“ nxYx AJU xk ^ il ^Ax^A^'YpAA, y u \Az

[0200] YQ IX

[0201] 30

[0202]

[0203] Foreignfiling text P25-161.docx

[0204] - 18 -

[0205] 5

[0206]

[0207] Further examples of suitable polymerizable compounds which can be used as comonomer in the composition of the present invention are (meth)acrylic compounds, styrene-based compounds vinyl-based compound, aryl-based 15

[0208] compounds and maleic compounds, as radical polymerizable compounds.

[0209] Examples of styrene-based compounds are as follows, but the compound is not limited to those examples: styrene, alkylstyrene such as 2,4-dimethyl-a- methylstyrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, 2,4- 20 dimethylstyrene, 2,5-dimethylstyrene, 2,6-dimethylstyrene, 3,4-dimethyl- styrene, 3,5-dimethylstyrene, 2,4,6-trimethylstyrene, 2,4,5-trimethylstyrene, pentamethylstyrene, o-ethylstyrene, m -ethylstyrene, p-ethylstyrene, diethylstyrene, triethylstyrene, propylstyrene, 2,4-diisopropylstyrene, butylstyrene, hexylstyrene, heptylstyrene, and octylstyrene; styrene halide such as fluorostyrene, o-chlorostyrene, m-chlorostyrene, p-chlorostyrene, o-bromo- styrene, m-bromostyrene, p-bromostyrene, dibromostyrene, and iodostyrene; compounds having a styryl group as a polymerizable functional group, such as nitrostyrene, acetylstyrene, o-methoxystyrene, m-methoxy- styrene, p-m ethoxystyrene, o-hydroxystyrene, m-hydroxystyrene, p- hydroxystyrene, 2-vinylbiphenyl, 3-vinylbiphenyl, 4-vinylbiphenyl, 1-vinyl- naphthalene, 2-vinylnaphthalene, 4-vinyl-p-terphenyl, 1-vinylanthracene, a- 30 methylstyrene, o-isopropenyltoluene, m-isopropenyltoluene, p-isopropenyl- toluene, 2,3-dimethyl-a-methylstyrene, 3,5- dimethyl-a-methylstyrene, p-Foreignfiling text P25-161.docx

[0210] - 19 -

[0211] isopropyl-a-methylstyrene, a-ethylstyrene, a-chlorostyrene, divinylbenzene and divinylbiphenyl.

[0212] Examples of vinyl-based compounds are as follows, but the compound is not limited to these examples: vinylpyridine, vinylpyrrolidone, vinyl- 5

[0213] carbazole, vinyl acetate, and acrylonitrile; conjugated diene monomers such as butadiene, isoprene, and chloroprene; vinyl halide such as vinyl chloride and vinyl bromide; a compound having a vinyl group as a polymerizable functional group, for example, vinylidene halide such as vinylidene chloride, vinyl ester of organic carboxylic acid and its derivatives, for example, vinyl acetate, vinyl propionate, vinyl butyrate, vinyl benzoate, and divinyl adipate, and (meth)acrylonitrile. In this specification, (meth)acrylonitrile is a general term for acrylonitrile and methacrylonitrile.

[0214] Examples of fumaric compounds are as follows, but the compound is not limited to these examples: dimethyl fumarate, diethyl fumarate, diisopropyl 15 fumarate, di-sec-butyl fumarate, diisobutyl fumarate, di-n-butyl fumarate, di- 2 -ethylhexyl fumarate and dibenzyl fumarate.

[0215] Examples of maleic compounds are as follows, but the compound is not limited to these examples: dimethyl maleate, diethyl maleate, diisopropyl maleate, di-sec-butyl maleate, diisobutyl maleate, di-n-butyl maleate, di-2- 20 ethylhexyl maleate, and dibenzyl maleate.

[0216] Other examples of the radical polymerizable compound are as follows, but the compound is not limited to these examples: dialkylester of itaconic acid and its derivative, for example, dimethyl itaconate, diethyl itaconate, diisopropyl itaconate, di-sec-butyl itaconate, diisobutyl itaconate, di-n-butyl itaconate, di-2-ethylhexyl itaconate, and dibenzyl itaconate, an N-vinyl- amide derivative of an organic carboxylic acid, for example, N-methyl-N- vinylacetamide, and maleimide and its derivative, for example, N-phenyl- maleimide and N-cyclohexylmaleimide.

[0217] 30 In a preferred embodiment of the present invention, the composition comprises acrylate monomers in a range from 0 to 10 wt.% based on the total amount of the composition and preferably in the range from 0 to 5Foreignfiling text P25-161.docx

[0218] -20 -

[0219] wt.%. More preferably, the composition does not comprise any acrylate monomers.

[0220] As another embodiment of the present invention, it is believed that adding small amount of acrylates may give flexibility on adjusting viscosity,

[0221] 5

[0222] inkjetability and / or vapor pressure of the composition. It can also increase photo curing speed of the composition.

[0223] The composition according to the present invention further comprises at least one polymerization initiator. It may comprise also two or more different polymerization initiators. The polymerization initiator is a compound that generates an acid, a base or a radical by irradiation, such as visible light, ultraviolet light or X-ray radiation, or that generates an acid, a base or a radical by heat. In a preferred embodiment of the invention, the polymerization initiator is a photoinitiator, i.e. a compound that generates an acid, a base or a radical by irradiation, in particular a radical.

[0224] 15

[0225] Preferably said polymerization initiator is a photo initiator, preferably selected from photo-radical initiators, photo-acid generators or a combination of photo-radical initiator and photo-acid generator. A photoradical initiator is a compound that generates a radical by irradiation.

[0226] 20 In this specification, the photopolymerization initiator is a compound that absorbs light having a predetermined wavelength and generates a radical, an acid or a base. More preferably, the photopolymerization initiator is a compound that generates a radical by irradiation, such as infrared light, visible light, ultraviolet light (UV light), far-ultraviolet light, X-ray, a charged particle beam such as an electron beam, preferably by irradiation with UV light. In one embodiment of the invention only one type of a photopolymerization initiator is used. In a further embodiment of the invention, a plurality of types of photopolymerization initiators is used.

[0227] Examples of photoinitiators which are radical generators are as follows, but 30 the radical generator is not limited to these examples: 2,4,5-triarylimidazole dimers that can have substituent groups, such as a 2-(o-chlorophenyl)-4,5- diphenylimidazole dimer, a 2-(o-chlorophenyl)-4,5-di(methoxyphenyl)-Foreignfiling text P25-161.docx

[0228] - 21 -

[0229] imidazole dimer, a 2-(o-fluorophenyl)-4,5-diphenylimidazole dimer, and a 2- (o- or p-methoxyphenyl)-4,5-diphenylimidazole dimer; benzophenone derivatives such as benzophenone, N,N-tetramethyl-4,4’-diaminobenzo- phenone (Michler’s ketone), N,N-tetraethyl-4,4’-diaminobenzophenone, 4- methoxy-4’-dimethylaminobenzophenone, 4-chlorobenzophenone, 4,4’- 5

[0230] dimethoxybenzophenone, and 4,4’-diaminobenzophenone; a-amino aromatic ketone derivatives such as 2-benzyl-2-dimethylamino-1-(4- morpholinophenyl)-butanone and 1 ,2-methyl-1 -[4-(methylthio)phenyl]-2- morpholino-propane-1-one; quinones such as 2-ethylanthraquinone, phenanthrenequinone, 2-t-butylanthraquinone, octamethylanthraquinone, 1.2-benzanthraquinone, 2,3-benzanthraquinone, 2-phenylanthraquinone, 2.3-diphenylanthraquinone, 1 -chloroanthraquinone, 2-methylanthraquinone, 1.4-naphthoquinone, 9, 10-phenanthraquinone, 2-methyl-1 ,4-naphto- quinone, and 2,3-dimethylanthraquinone; benzoin ether derivatives such as benzoin methyl ether, benzoin ethyl ether, and benzoin phenyl ether; benzoin derivatives such as benzoin, methyl benzoin, ethyl benzoin, and 15 propyl benzoin; benzyl derivatives such as benzyldimethylketal; acridine derivatives such as 9-phenylacridine and 1 ,7-bis(9,9’-acridinyl)heptane; N- phenylglycine derivatives such as N-phenylglycine; acetophenone derivatives such as acetophenone, 3-methylacetophenone, acetophenone benzylketal, 1 -hydroxycylohexyl phenylketone, and 2,2-dimethoxy-2-phenyl acetophenone; thioxanthone derivatives such as thioxanthone, diethylthio20 xanthone, 2-isopropylthioxanthone, and 2-chlorothioxanthone; acylphosphine oxide derivatives such as 2,4,6-(trimethylbenzoyl)phenyl- phosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, and bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide; oxime ester derivatives; and xanthone, fluorenone, benzaldehyde, fluorene, anthraquinone, triphenylamine, carbazole, 1-(4-isopropylphenyl)-2-hydroxy- 2-methylpropane-1 -one; and 2-hydroxy-2-methyl-1 -phenylpropane-1 -one.

[0231] Examples of commercially available products of the above-described radical generators are as follows, but the products are not limited to these examples: Irgacure 184, 369, 651 (Merck, CAS: 24650-42-8), 500, 819 30 (Merck, CAS: 162881-26-7), 907, 784, and 2959, Irgacure OXE02 (Boc Sciences, CAS: 478556-66-0), CGI-1700, -1750, and -1850, CG24-61, Darocur 1116 and 1173, Lucirin® TPO, LR8893, and LR8970 (BASF),Foreignfiling text P25-161.docx

[0232] - 22 -

[0233] Ubecryl P36 (UCB) and Omnirad 1316 (IGM Resins). Furthermore, polymerization initiators as disclosed in EP 3717966 A1 or WO 2021 / 099236 A1 can be used.

[0234] Preferred commercially available radical generators are Omnirad 1316 and 5

[0235] Omnirad 651.

[0236] In a further preferred embodiment of the present invention, the content of the photo initiator is in the range from 0.5 to 10 wt%, preferably 1 to 8 wt%, and most preferred 2 to 6 wt% based on the composition.

[0237] Alternatively, an acid generator or a base generator may be used as polymerization initiator.

[0238] Examples of photoacid generators include diazomethane compounds, triazine compounds, sulfonate esters, iodonium salts such as diphenyl- 15 iodonium salts, sulfonium salts such as triphenylsulfonium salts, ammonium salts, phosphonium salts, and sulfonimide compounds.

[0239] Examples of photobase generators include multi-substituted amide compounds having an amide group, lactams, imide compounds; and ionic photobase generators containing anions such as amide anions, methide 20 anions, borate anions, phosphate anions, sulfonate anions, or carboxylate anions.

[0240] Examples of thermal acid generators include aliphatic sulfonic acids and their salts; aliphatic carboxylic acids such as citric acid, acetic acid, maleic acid, and their salts; aromatic carboxylic acids such as benzoic acid, phthalic acid, and their salts; aromatic sulfonic acids and their salts; aromatic diazonium salts; and phosphonic acids and their salts.

[0241] Examples of thermal base generators include compounds that generate bases such as imidazoles and tertiary amines.

[0242] 30

[0243] In a further embodiment, the composition of the present invention comprises a solvent or a mixture of solvents in a total amount of 10 wt.% orForeignfiling text P25-161.docx

[0244] - 23 -

[0245] less based on the total amount of the composition. Preferably, the solvent content is in the range from 0 to 10 wt.%, more preferably it is in the range from 0 to 5 wt%. The term ..solvent" relates to a compound that can dissolve or disperse the polymerizable compounds, but does not itself polymerize during the photocuring of the composition. By addition of a small amount of 5

[0246] solvent, the viscosity of the composition according to the invention can be lowered.

[0247] In a preferable embodiment of the present invention, the boiling point of the solvent at 1 atm is in the range from 60 to 200 °C. preferably from 70 to 180 °C. more preferably from 80 to 160 °C and most preferably from 80 to 145 °C.

[0248] In one embodiment of the present invention, the solvent comprises one or more hydroxy groups or -CO-O- groups. Preferably, the solvent is an alcohol or an ester, more preferably a primary or secondary alcohol or an 15 ester, further preferably a secondary alcohol or an ester.

[0249] In another preferable embodiment of the present invention, the molecular weight of the solvent is in the range from 40 to 160 g / mol, preferably 50 to 140 g / mol. more preferably 60 to 120 g / mol.

[0250] 20 The solvent can be selected, for example, from alcohols, ketones, ethers, esters, nitrogen-containing solvents and / or aromatic solvents.

[0251] Examples of alcohol-based solvents are methanol, ethanol, n-propanol, i- propanol, n-butanol, i-butanol, sec-butanol, t-butanol, n-pentanol, i- pentanol, 2-methylbutanol, sec-pentanol, t-pentanol, 3-methoxybutanol, n- hexanol, 2-methylpentanol, sec-hexanol. 2-ethylbutanol, sec-heptanol, heptan-3-ol, n-octanol, 2-ethylhexanol, 4-methyl-2-pentanol, 3-methyl-2- pentanol, 2-methyl-2-pentanol, 3-methyl-2-butanol, 2-methyl-2-butanol, 4- methyl-2-hexanol, 5-methyl-2-hexanol, 3-methyl-2-hexanol, 2-methyl-2- hexanol, sec-octanol, n-nonyl alcohol. 2,6-dimethylheptanol-4, n-decanol, 30 sec-undecyl alcohol, trimethylnonyl alcohol, sec-tetradecyl alcohol, secheptadecyl alcohol, phenol, cyclohexanol, methylcyclohexanol, 3.3.5- trimethylcyclohexanol, benzyl alcohol, phenylmethylcarbinol, diacetoneForeignfiling text P25-161.docx

[0252] -24 -

[0253] alcohol, cresol, ethylene glycol, propylene glycol, 1,3-butylene glycol, pentane-2,4-diol, 2-methylpentane-2,4-diol, hexane-2,5-diol, heptane-2,4- diol, 2-ethyl-1 ,3-hexanediol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol and glycerin.

[0254] 5

[0255] Examples for ketone-based solvents are acetone, methylethylketone, methyl-n-propylketone, methyl-n-butylketone, diethylketone, methyl-iso- butylketone, methyl-n-pentylketone, ethyl-n-butylketone, methyl-n-hexyl- ketone, di-iso-butylketone, trimethylnonanone, cyclopentanone, cyclohexanone, methylcyclohexanone, 2,4-pentanedione, acetylacetone and acetophenone.

[0256] Examples of ether-based solvents are ethyl ether, iso-propyl ether, n-butyl ether, n-hexyl ether, 2-ethylhexyl ether, ethylene oxide, 1 ,2-propylene oxide, dioxolane, 4-methyldioxolane, dioxane, dimethyldioxane, 2-methoxy- ethanol, 2-ethoxyethanol, ethylene glycol monomethyl ether, ethylene 15 glycol monoethyl ether, ethylene glycol diethyl ether, ethylene glycol mono- n-butyl ether, ethylene glycol mono-n-hexyl ether, ethylene glycol monophenyl ether, 2-n-butoxyethanol, 2-n-hexoxyethanol, 2-phenoxyethanol, 2- (2-ethylbutoxy)ethanol, ethylene glycol dibutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol diethyl ether, diethylene glycol mono-n-butyl ether, diethylene glycol di-n- 20 butyl ether, diethylene glycol mono-n-hexyl ether, ethoxy triglycol, tetraethylene glycol di-n-butyl ether, 1-n-butoxy-2-propanol, 1-phenoxy-2- propanol, propylene glycol monomethyl ether (PGME), propylene glycol monomethyl ether acetate (PGMEA), propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, tetrahydrofuran (THF), and 2-methyl- tetrahydrofuran.

[0257] Examples of ester-based solvents are diethyl carbonate, methyl acetate, 30 ethyl acetate, amyl acetate, y-butyrolactone, y-valerolactone, n-propyl acetate, iso-propyl acetate, n-butyl acetate, iso-butyl acetate, sec-butyl acetate, n-pentyl acetate, sec-pentyl acetate, 3-methoxybutyl acetate,Foreignfiling text P25-161.docx

[0258] - 25 -

[0259] methylpentyl acetate, 2-ethylbutyl acetate, 2-ethylhexyl acetate, methyl 2- hydroxyisobutyrate, methyl 2-hydroxybutyrate, methyl 3-hydroxybutyrate, methyl 4-hydroxy butyrate, ethyl 2-hydroxyisobutyrate, ethyl 2-hydroxy- butyrate, ethyl 3-hydroxybutyric acid, ethyl 4-hydroxybutyratebenzyl acetate, cyclohexyl acetate, methylcyclohexyl acetate, n-nonyl acetate, 5

[0260] methyl acetoacetate, ethyl acetoacetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol mono-n-butyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol monobutyl ether acetate, dipropylene glycol monomethyl ether acetate, dipropylene glycol monoethyl ether acetate, glycol diacetate, methoxy triglycol acetate, ethyl propionate, n-butyl propionate, iso-amyl propionate, diethyl oxalate, di-n-butyl oxalate, methyl lactate, ethyl lactate (EL), propyl lactate, n-butyl lactate, n-amyl lactate, diethyl malonate, dimethyl phthalate, and diethyl phthalate.

[0261] 15

[0262] Examples of nitrogen-containing solvents are N-methylformamide, N,N- dimethyl formamide (DMF), N,N-diethylformamide, acetoamide, N-methyl- acetoamide, N,N-dimethylacetoamide, N-methylpropionamide, and N- methylpyrrolidone.

[0263] 20 Examples of aromatic solvents are toluene and anisole.

[0264] Preferably, the solvent is selected from one or more solvents of the group consisting of i-propanol, PGME, PGMEA, EL, toluene, n-butyl acetate, anisole, cyclopentanone and cyclohexanone, and more preferably selected from one or more members of the following group consisting of i-propanol, n-butyl acetate, PGME, PGMEA, anisol and EL.

[0265] The composition of the present invention may also comprise a mixture of two or more different solvents.

[0266] 30 The composition may further include one or more additives. Examples of additives include surfactants, adhesion promoters, corrosion resistance additives, crosslinking agents, dispersants, fillers, functional pigments (suchForeignfiling text P25-161.docx

[0267] -26 -

[0268] as those providing functional effects like conductivity, thermal conductivity, magnetic properties), nanoparticles, particles that reduce thermal expansion, polymerization inhibitors, rheology modifiers (such as thickeners), and adhesion enhancers.

[0269] 5

[0270] The content of additives is preferably 0 to 10 wt%, more preferably 0 to 8 wt%, further preferably 0 to 6 wt%, and furthermore preferably 0 to 5 wt%, based on all components of the composition. It is also a preferable embodiment that the composition does not contain any additives.

[0271] Examples of surfactants include fluorine-containing surfactants, nonionic surfactants, anionic surfactants, amphoteric surfactants, silicon-containing surfactants and any combination thereof. Examples of the fluorine- containing surfactants include surfactants having fluorinated hydrocarbon groups and hydrophilic groups, such as Megaface (DIC), Florad (3M), and Surfion (AGC Seimi Chemical).

[0272] 15

[0273] Nanoparticles may be selected from particles of nitrides, titanates, diamonds, oxides, sulfides, sulfites, sulfates, silicates, and carbides.

[0274] Nanoparticles can be optionally surface-modified using capping agents. The particle size of nanoparticles may be in the range from 1 to 100 nm, 1 to 50 nm, or 1 to 25 nm. The particle size can be measured by any

[0275] 20 standard method known to those skilled in the art.

[0276] Examples of polymerization inhibitors include ultraviolet absorbers, as well as nitrones, nitrogen oxide radicals, hydroquinones, catechols, phenothiazines, phenoxazines, hindered amines, and their derivatives. Preferably, methylhydroquinone, catechol, 4-t-butylcatechol, 3- methoxycatechol, phenothiazine, chlorpromazine, phenoxazine, hindered amines such as TINUVIN 144, 292, and 5100 (BASF), and ultraviolet absorbers such as TINUVIN 326, 328, 384-2, 400, and 477 (BASF) can be used.

[0277] 30 Adhesion enhancers are effective in preventing the coating film from peeling off the substrate due to stress applied during curing by heating when a composition according to one embodiment is applied to a substrateForeignfiling text P25-161.docx

[0278] -27 -

[0279] to form a film. Preferred adhesion enhancers include imidazole compounds and silane coupling agents. Examples of imidazole compounds include 2- hydroxybenzimidazole, 2-hydroxyethylbenzimidazole, benzimidazole, 2- hydroxyimidazole, imidazole, 2-mercaptoimidazole, and 2-aminoimidazole. Examples of silane coupling agents include epoxy silane coupling agents, 5

[0280] amino silane coupling agents, and mercapto silane coupling agents.

[0281] Preferred examples include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxy- propyltriethoxysilane, N-2-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N- 2-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxy- silane, 3-aminopropyltriethoxysilane, 3-ureidopropyltriethoxysilane, 3- chloropropyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, and 3- isocyanatopropyltriethoxysilane.

[0282] It is believed that surfactants and release agents can be used to reduce adhesion force of the composition, preferably to the superstrate material for improved processibility.

[0283] 15

[0284] In a preferred embodiment of the present invention, the viscosity of the composition at 23 °C is in the range from 2 to 100 cP, preferably from 2 to 50 cP, more preferably from 5 to 20 cP, and most preferably from 7 to 20 cP from the viewpoint of realizing smooth inkjetting. The viscosity of the composition can be measured using an Anton Paar MCR 92 rheometer 20 (Anton Paar, Graz, Austria) using a cone-plate geometry. The viscosity value is determined at a shear rate of 500 s_1using a rotational cone-plate geometry (d = 25 mm) at 23 °C.

[0285] The viscosity of the composition can be controlled, for example, by the choice of the monomer of formula (1 ) and / or the second monomer, as well as their amounts in the composition and the presence or absence and the choice and amount of solvents.

[0286] The surface tension of the curable composition of the present invention at 23 °C of the composition containing the components except for the solvent 30 is preferably from 5 mN / m to 70 mN / m, more preferably from 7 mN / m to 50 mN / m, and further preferably from 10 mN / m to 40 mN / m. Note that when the surface tension is high, for example, 5 mN / m or more, the capillarityForeignfiling text P25-161.docx

[0287] - 28 -

[0288] strongly acts, so filling (spreading and filling) is complete within a short time period when the curable composition and a mold are brought into contact with each other. Also, when the surface tension is 70 mN / m or less, a cured film obtained by curing the curable composition has surface smoothness.

[0289] 5

[0290] The contact angle of the curable composition of the present invention of the composition containing the components except for the solvent is preferably in the range from 0° to 90° and particularly preferably from 0° to 10° with respect to both the surface of a substrate and the surface of a mold. If the contact angle is larger than 90°, the capillarity acts in a negative direction (a direction in which the contact interface between the mold and the curable composition is shrunk) inside a pattern of the mold or in a gap between the substrate and the mold, and this may make filling impossible. When the contact angle is small, the capillarity strongly acts, and the filling rate increases.

[0291] 15 In another aspect, the present invention relates to method for preparing the composition of the present invention, comprises mixing at least one compound of formula (1) and at least one photoinitiator and optionally further compounds, such as one or more further monomers, one or more solvents and / or one or more further additives.

[0292] 20 In another aspect, the present invention further relates to process for preparing the cured layer, comprising the following steps in the following order:

[0293] (i) forming a layer of the composition of the invention on a substrate, for example by a process such as printing, in particular inkjet printing, spincoating or slit coating;

[0294] (ii) optionally bringing the layer into contact with a template, such as a superstrata;

[0295] (iii) curing the composition by heat and / or by irradiation of the layer with light to form a cured layer;

[0296] (iv) optionally removing the template from the cured layer.

[0297] 30

[0298] The process steps (i) and (iii) are obligatory process steps while steps (ii) and (iv) are optional. If a template is used in step (ii), the template can beForeignfiling text P25-161.docx

[0299] -29 -

[0300] patterned or not patterned. In a preferred embodiment, the template is not patterned. One embodiment of a template, which is not patterned, is the superstrate in an IAP process. The use of a superstrata is generally known in the art. For example, the superstrate and a method of use is described in Niyaz Khusnatdinov et al., “Development of an inkjet-enabled Adaptive 5

[0301] Planarization Process", Proceedings Volume 10451, Photomask Technology 2017; 104511 A (2017).

[0302] The term “on a substrate” in step (i) means that the composition according to the present invention may be applied either directly or via one or more other layers (hereinafter, referred to as “the underlayer”) on the substrate. Examples of the underlayer include a SOC (Spin on Carbon), an adhesion enhancing film. In a preferred embodiment of the invention, the layer of the composition is formed directly on the substrate. Examples of the substrate include a silicon substrate, a glass substrate and a resin film. The substrate may be patterned. The layer of the composition of the invention obtained 15 after step (i) is a liquid layer.

[0303] The formation of the layer is preferably achieved by inkjet printing, printing droplet of the composition of the present invention from an inkjet nozzle of an inkjet device. The fluid pressure of the inkjet device is usually in the range from 0.1 to 3 MPa. The volume of each printed droplet is usually in 20 the range from 50 to 300 nl.

[0304] The adhesion of the surface of the substrate to the composition may be improved by treatments, such as a silane coupling treatment, a silazane treatment, or deposition of an organic thin film.

[0305] After performing step (i) and before performing step (ii) or (iii), it can be preferred to wait for the arranged droplets to combine with their respective adjacent droplets to from a continuous liquid film on the substrate, in the following referred to as step (i-a). The duration of this step is preferably in the range from 0.1 to 600 sec, more preferably from 10 to 300 sec.

[0306] 30

[0307] In a further preferred embodiment of the present invention, the arranged droplets of the step (i) are heated during all or parts of step (i-a). TheForeignfiling text P25-161.docx

[0308] - 30 -

[0309] duration of the heating is preferably in the range from 10 to 600 sec, more preferably 50 to 500 sec, and further preferably 100 to 400 sec. The heating temperature is preferably in the range from 30 to 200 °C, more preferably 50 to 180 °C. The heating of the step (i-a) may be conducted in an oxygen gas atmosphere, air, or an atmosphere of an inert gas such as nitrogen. 5

[0310] When heating is performed by multiple steps, the steps may be conducted under different atmospheric conditions. In the present invention, the oxygen gas atmosphere means that the partial pressure of the oxygen gas is at least 50% of the total pressure. In the present invention, the nitrogen gas atmosphere means that the partial pressure of the nitrogen gas is at least 90% of the total pressure. A nitrogen gas atmosphere is understood as inert atmosphere.

[0311] Examples of the superstrate to be used in the step (ii) include a silicon substrate, a glass substrate, such as a quartz glass substrate, and a resin film. The superstrate may be patterned on its surface. The pattern on the 15 surface of the superstrate may have a height of 4 nm to 200 nm. The pressure to be applied to the composition when bringing the superstrate into contact with the composition is preferably in the range from 0 MPa to 100 MPa, more preferably 0 MPa to 50 MPa, further preferably 0 MPa to 20 MPa.

[0312] 20 In some embodiments, said curing step (iii) can be photo curing, i.e. curing by irradiation of light, heat curing or a combination of photo curing and heat curing.

[0313] In a preferred embodiment, said photo curing is performed by irradiating the composition with light, preferably UV light, with an energy in the range from 0.1 to 30 J / cm2, more preferred from 0.3 to 25 J / cm2and most preferred from 0.5 to 2 J / cm2. The preferred light wavelength is in the range from 150 to 450 nm, preferably 200 to 440 nm, more preferably 250 to 410 nm, more preferably 300 to 380 nm and most preferably around 350 nm.

[0314] 30 Examples of a light source that emits the light of the step (iii) are an LED lamp, a high-pressure mercury lamp, an ultrahigh-pressure mercury lamp, a low-pressure mercury lamp, a Deep-UV lamp, a carbon arc lamp, a metalForeignfiling text P25-161.docx

[0315] - 31 -

[0316] halide lamp, a xenon lamp, a KrF excimer laser, an ArF excimer laser or an F2 laser.

[0317] In a further embodiment, the process for preparing a cured layer comprises a baking step which is performed after the curing step (iii). This baking step 5

[0318] is preferably performed at a temperature in the range from 180 to 450 °C , particularly preferably in the range from 200 to 350 °C and most preferably in the range from 220 to 320 °C.

[0319] It is further possible to perform a further heating step after removal of the template or superstrate, i.e. after performing step (iv).

[0320] When the glass transition temperature is sufficiently higher than the temperature used during the removal of the template, a cured product shows a strong glass state, that is, a high mechanical strength during template removal, so pattern collapse or break hardly occurs due to impact 15 of template removal. When performing step (iv), i.e. the template removal, at room temperature, therefore, the glass transition temperature of the cured product is preferably 70 °C or more, more preferably 100 °C or more, and further preferably 150 °C more. The glass transition temperature of the cured product can be measured by using differential scanning calorimetry (DSC) or a dynamic viscoelasticity apparatus.

[0321] 20

[0322] In another aspect, the present invention also relates to a method of manufacturing a device comprising the following steps (i) and (ii):

[0323] (i) forming a cured film by the method of the present invention;

[0324] (ii) processing the substrate.

[0325] The device manufactured by the method is preferably a semiconductor device.

[0326] The processing of the step (ii) may comprise one or more etching processes to transfer a relief image into the substrate. The relief image 30 corresponds to the pattern in the patterned layer or an inverse of that pattern. The processing of the step (ii) may further comprise processes selected from one or more members of the group consisting of inspection,Foreignfiling text P25-161.docx

[0327] - 32 -

[0328] layer formation, deposition, doping, etching, formable material removal, dicing, bonding, packaging, mounting and circuit board assembly.

[0329] In a preferred embodiment, said method for preparing the cured layer is an Inkjet Adaptive Planarization (IAP) process.

[0330] 5

[0331] In another aspect, the present invention further relates to a cured layer, preferably a photo-cured layer. More preferably, this cured layer is obtained or can be obtained through a combination of photo-curing and thermal curing (dual-cured) using the method of the present invention. The combination of a substrate and a photocured layer overlying the substrate is called a laminate.

[0332] In another aspect, the present invention also relates to a cured layer, preferably it is a photo-cured layer, and more preferably a dual-cured layer, formed from the composition of the present invention. The photocured layer 15 may be used as an interlayer insulating film of a semiconductor device, such as LSI, system LSI, DRAM, SDRAM, RDRAM or D-RDRAM, or as a resist film used in a semiconductor manufacturing process.

[0333] It is preferable that the photocured layer has a carbon content of at least 70 %, more preferably at least 80 % and most preferably at least 85 %. The 20 carbon content of the photocured layer can be determined by elemental analysis using standard commercial analytical measurement techniques.

[0334] It is furthermore preferable that the photocured layer has a high thermal stability. Preferably, the onset temperature for thermal degradation of the photocured layer is > 250 °C, more preferably > 300 °C, more preferably > 350 °C, more preferably > 375 °C and most preferably > 400 °C. As used herein, the onset thermal degradation temperature is also called “thermal degradation temperature” and relates to the temperature in the TGA curve wherein a deflection of the curve from the almost linear plateau is first observed, shortly before the steep degradation decline of the sample.

[0335] 30

[0336] In another aspect, the present invention further relates to a stacked layer comprising a substrate and the cured layer of the present invention at leastForeignfiling text P25-161.docx

[0337] - 33 -

[0338] partly overlying the substrate. As the other aspect, the present invention provides a method of manufacturing of the stacked layer as described above.

[0339] The preferred compounds of formula (1) comprising at least two vinyl 5

[0340] groups are novel. A further aspect of the present invention is therefore a compound of the following formula (T)

[0341]

[0342] Formula (T)

[0343] 15 wherein R1, R2, o and p have the same meanings as discussed above and furthermore:

[0344] n is 1 , 2 or 3;

[0345] m is 0, 1 , 2 or 3;

[0346] 20

[0347] with the proviso that n + m > 2.

[0348] The definitions and preferred embodiments disclosed above for the compound of formula (1) in the composition according to the invention also apply to the compound of formula (T), as described above.

[0349] The present invention is further illustrated by the examples following hereinafter which shall not be construed as limiting. The skilled person will acknowledge that various modifications, additions and alternations may be made to the invention without departing from the spirit and scope of the 30 invention as defined in the appended claims.Foreignfiling text P25-161.docx

[0350] -34 -

[0351] The present invention provides one or more of the following technical effects: improved thermal stability after curing, preferably at about 350 °C or more; lower shrinkage after curing; improved etching resistance of a cured layer; improved planarization performance of a cured layer, namely over different pattern topographies of a substrate; low viscosity and / or low vapor 5

[0352] pressure as a composition, preferably suitable for ink-jet printing; applicable for ink-jet printing to make a cured layer(s); and providing a cured layer with mechanical durability.

[0353] In particular, the composition of the present invention results in an improvement of the thermal stability of the cured layer, as well as an improved outgassing behavior of the cured layer.

[0354] Brief description of the drawings

[0355] Fig. 1 shows the isothermal baking comparison of W.E. 1 (solid line) and W.E. 2 (dotted line). The samples are heated to 400 °C and then

[0356] 15 maintained at this temperature for an additional 60 minutes. W.E. 1 contains 10 wt% of Example 2, while W.E. 2 includes 10 wt% of a comparable compound from prior art.

[0357] Fig. 2 shows the isothermal baking comparison of W.E. 3 (dahsed line), W.E. 4 (dotted line) and W.E. 5 (solid line). The samples are heated to 20 425 °C and maintained at this temperature for an additional 60 minutes.

[0358] W.E. 3 contains 25 wt% of Example 1 , W.E. 4 comprises 50 wt% of Example 1 , while W.E. 5 consists of the state-of-the-art material Example 4.

[0359] Fig. 3 shows the TGA comparison up to 500 °C of W.E. 3 (dashed line), W.E. 4 (dotted line) and W.E. 5 (solid line). W.E. 3 contains 25 wt% of Example 1 , W.E. 4 comprises 50 wt% of Example 1 , while W.E. 5 consists of the state-of-the-art material Example 4.

[0360] Fig. 4 shows the isothermal baking comparison of W.E. 6 (dashed line), W.E. 7 (solid line) and W.E. 8 (dotted line). The samples are heated to 30 425 °C and maintained at this temperature for an additional 60 minutes.

[0361] W.E. 6 contains 10 wt% of Example 1 , W.E. 7 comprises 50 wt% of Example 1 , while W.E. 8 consists of the state-of-the-art material Example 4.Foreignfiling text P25-161.docx

[0362] - 35 -

[0363] Fig. 5 shows the TGA comparison up to 500 °C of W.E. 6 (dashed line), W.E. 7 (solid line) and W.E. 8 (dotted line). W.E. 6 contains 10 wt% of Example 1 , W.E. 7 comprises 50 wt% of Example 1 , while W.E. 8 consists of the state-of-the-art material Example 4.

[0364] 5

[0365] Examples

[0366] Part A: Synthesis of preferred specific examples

[0367] Example 1: 1,3-divinyl-5-(1-(3-vinylphenyl)vinyl)benzene

[0368] Step 1: Synthesis of (3-bromophenyl)(3,5-dibromophenyl)methanone

[0369] N

[0370] 15 I nBuLi

[0371] Et2O

[0372]

[0373] -78 °C To a dry flask, 1 ,3,5-tribromobenzene (Merck, CAS: 626-39-1, 7 g, 22.3 mmol) was added, followed by 70 mL of dry diethyl ether (Merck). The system was purged with argon to create an inert atmosphere. The flask was 20 cooled to -78 °C using a dry ice / acetone bath. Next, n-butyllithium (Merck,

[0374] 1.6 M in n-hexane, 15.2 mL, 24.3 mmol, 1.2 eq) was added slowly and dropwise, ensuring that the internal temperature did not exceed -70 °C. After the addition was complete, the mixture was treated with 3-bromo-N- methoxy-N-methylbenzamide (BLD Pharma, CAS: 207681-67-2, 5 g, 20.3 mmol), which had been dissolved in 5 mL of dry diethyl ether. The reaction mixture was stirred for an additional hour at -70 °C, followed by overnight stirring at room temperature. Subsequently, 1 M HCI (22.3 mL, 22.31 mmol) was added dropwise while maintaining the temperature at 0 °C. The mixture was stirred for 2 hours at room temperature. After this, the phases were separated, and the aqueous phase was extracted three times with MTBE (methyl tert-butyl ether). The organic phases were combined, 30 washed with brine, dried over Na2SO4, filtered, and evaporated to remove the solvent. The crude product was then purified using silica gelForeignfiling text P25-161.docx

[0375] - 36 -

[0376] chromatography with a heptane / ethyl acetate (9:1) mixture as the eluent. This process yielded 6.3 g (74%) of the product as a yellow solid.

[0377] 1H NMR (500 MHz, Chloroform-d): 5 = 7.94 (dt, J = 10.7, 1.8 Hz, 2H), 7.84 (d, J = 1.8 Hz, 2H), 7.79 (ddd, J = 8.0, 2.0, 1.0 Hz, 1 H), 7.69 (dt, J = 7.7, 1.3 Hz, 1 H), 7.42 (t, J = 7.9 Hz, 1 H) ppm.

[0378] 5

[0379] Step 2: Synthesis of 1,3-dibromo-5-(1-(3-bromophenyl)vinyl)benzene o II

[0380]

[0381] Methyltriphenylphosphonium bromide (Merck, CAS: 1779-49-3, 7 g, 19.6 mmol) was dissolved in 80 mL of dry THF (Merck) and cooled to -18 °C. Potassium fe / t-butoxide (Merck, CAS: 865-47-4, 2.2 g, 19.6 mmol) was added stepwise, and the mixture was stirred for 10 minutes at -18 °C.

[0382] Subsequently, (3-bromophenyl)(3,5-dibromophenyl)methanone (step 1, 6.3 15 g, 15 mmol), which had been dissolved in 50 mL of THF, was added while keeping the temperature below 0 °C. The reaction mixture was stirred overnight at room temperature, then cooled again and quenched carefully with water. The mixture was diluted with MTBE, and the phases were separated. The aqueous phase was extracted three times with MTBE, and the combined organic phases were washed with brine, dried over Na2SO4, 20 filtered, and evaporated to dryness. Finally, the crude product was purified using silica gel chromatography with heptane as the eluent, yielding 3.6 g (57%) of a colorless oil.

[0383] 1H NMR (500 MHz, Chloroform-d): 5 = 7.66 (t, J = 1.8 Hz, 1 H), 7.55 - 7.45 (m, 2H), 7.40 (d, J = 1.7 Hz, 2H), 7.29 - 7.18 (m, 2H), 5.53 (d, J = 11.8 Hz, 2H) ppm.

[0384] Step 3: Synthesis of 1,3-divinyl-5-(1-(3-vinylphenyl)vinyl)benzene

[0385]

[0386] 30 KOH (7.4 g, 132 mmol) was dissolved in 29.3 mL of water and treated with potassium vinyltrifluoroborate (abcr, CAS: 13682-77-4, 4.9 g, 36 mmol,Foreignfiling text P25-161.docx

[0387] - 37 -

[0388] 3.3 eq). Subsequently, 1 ,3-dibromo-5-(1-(3-bromophenyl)vinyl)benzene (step 2, 4.6 g, 11 mmol), which had been dissolved in 45 mL of dry THF, was added stepwise, and the reaction mixture was purged with argon for 15 minutes. A palladium catalyst (Merck, CAS: 887919-35-9, 0.3 g, 0.44 mmol) was added, and the reaction mixture was heated at 50 °C overnight. After 5

[0389] this period, the mixture was cooled to room temperature, treated with water, and the phases were separated. The aqueous phase was extracted three times with heptane, and the combined organic phases were dried over Na2SO4, filtered, and the solvent was removed. The crude product was finally purified using a silica plug with heptane, resulting in 2.4 g (82%) of a colorless oil.

[0390] 1H NMR (700 MHz, Chloroform-d): 5 = 7.45 (t, J = 1.7 Hz, 1 H), 7.42 (dd, J = 6.9, 1.5 Hz, 2H), 7.35 - 7.31 (m, 1 H), 7.29 (d, J = 1.6 Hz, 2H), 7.25 (dt, J = 7.7, 1.5 Hz, 1H), 6.74 (ddd, J = 17.6, 10.8, 5.3 Hz, 3H), 5.78 (ddd, J = 17.8, 4.5, 0.8 Hz, 3H), 5.52 (dd, J = 12.2, 1.2 Hz, 2H), 5.31 - 5.25 (m, 3H) ppm.

[0391] 15 Example 2: 4,4’-(ethene-1,1-diyl)bis(vinylbenzene)

[0392] Step 1: Synthesis of 4,4’-(ethene-1,1-diyl)bis(bromobenzene) o 20

[0393] The protocol followed the synthesis described in Example 1 , step 2, using 4,4’-dibromobenzophenone (Merck, CAS: 3988-03-2, 10 g, 29.4 mmol), which resulted in 7.5 g (75 %) of the desired product as colorless solid.

[0394] 1H NMR (500 MHz, Chloroform-d): 5 = 7.41 - 7.35 (m, 4H), 7.21 - 7.07 (m, 4H), 5.38 (s, 2H) ppm.

[0395] Step 2: Synthesis of 4,4’-(ethene-1 ,1-diyl)bis(vinylbenzene)

[0396] 30

[0397]

[0398] Foreignfiling text P25-161.docx

[0399] - 38 -

[0400] The protocol followed the synthesis described in Example 1 , step 3, using 4,4’-(ethene-1 ,1-diyl)bis(bromobenzene) (step 1, 17.8 mmol), which resulted in 4 g (97 %) of the desired product as colorless solid.

[0401] 1H NMR (500 MHz, Chloroform-d): 5 = 7.41 (d, J = 8.1 Hz, 4H), 7.39 - 7.31 (m, 4H), 6.76 (dd, J = 17.6, 10.9 Hz, 2H), 5.83 - 5.76 (m, 2H), 5.49 (d, J = 5

[0402] 0.8 Hz, 2H), 5.29 (d, J = 10.9 Hz, 2H) ppm.

[0403] Example 3: 5,5’-(ethene-1,1-diyl)bis(1,3-divinylbenzene)

[0404] Step 1: Synthesis of bis(3,5-dibromophenyl)methanone

[0405]

[0406] 1 ,3,5-Tribromobenzene (Merck, CAS: 626-39-1, 50 g, 159 mmol) was placed in 654 mL of dry diethyl ether (Merck) and overlaid with argon. The mixture was cooled to -78 °C using a dry ice / acetone bath. / V-Butyllithium (2.5 M in n-hexane, 71.2 mL, 178 mmol, 1.1 eq) was added slowly and dropwise, ensuring that the internal temperature did not exceed -70 °C. The mixture was then treated with dimethylcarbamyl chloride (Merck, CAS: 79-44-7, 6.8 g, 63.5 mmol), which had been dissolved in 20 mL of dry diethyl ether. The reaction was stirred for an additional hour at -70 °C and then allowed to stir overnight at room temperature, resulting in the formation of a precipitate. Distilled water and glacial acetic acid were added dropwise at -5 °C, and the mixture was stirred for 2 hours at room temperature. The resulting solid was collected by filtration, washed with ethanol, and dried under vacuum, yielding 54 g (68%) of a pale yellow solid.

[0407] 1H NMR (500 MHz, Chloroform-d): 5 = 7.85 (s, 2H), 7.73 (s, 4H) ppm.

[0408] Step 2: Synthesis of 5,5’-(ethene-1 ,1-diyl)bis(1 ,3-dibromobenzene)

[0409] 30Foreignfiling text P25-161.docx

[0410] - 39 -

[0411] CHoPPhoBr

[0412] t-BuOK

[0413]

[0414] THF Br Br

[0415] The protocol follows the synthesis described in Example 1 , step 2, using 5

[0416] bis(3,5-dibromophenyl)methanone.

[0417] Step 3: Synthesis of 5,5’-(ethene-1 ,1-diyl)bis(1 ,3-divinylbenzene)

[0418]

[0419] The protocol follows the synthesis described in Example 1 , step 3, using 5,5’-(ethene-1 , 1 -d iy l)bis( 1 ,3-dibromobenzene).

[0420] 15 Example 4 (prior art): 1,3-divinyl-5-(3-vinylbenzyl)benzene

[0421]

[0422] Step 1: Synthesis of (3-bromophenyl)(3,5-dibromophenyl)methanol 20

[0423] nBuLi Et2O

[0424]

[0425] -78 °C

[0426] 1 ,3,5-Tribromobenzene (Merck, CAS: 626-39-1, 35 g, 111 mmol) was dissolved in dry diethyl ether (Merck, 500 mL). The suspension was cooled to -78 °C, and a solution of n-butyllithium (2.5 M in hexane, 44.5 mL, 111 mmol) was added dropwise. The reaction mixture was stirred at this temperature for 1 hour. Subsequently, 3-bromobenzaldehyde (Merck, CAS: 3132-99-8, 20.6 g, 111 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature and was carefully quenched with 250 mL water. The organic layer was washed three times with deionized 30

[0427] water. Afterwards, the solvent was removed under vacuum at 40 °C,Foreignfiling text P25-161.docx

[0428] -40 -

[0429] yielding a beige-brown residue weighing 40.7 g, which corresponded to a yield of 87%.

[0430] 1H NMR (500 MHz, Chloroform-d): 5 = 7.59 (t, J = 1.8 Hz, 1 H), 7.52 (d, J = 1.9 Hz, 1 H), 7.46 (d, J = 1.9 Hz, 3H), 7.25 (d, J = 7.4 Hz, 2H), 5.71 (s, 1 H) ppm.

[0431] 5

[0432] Step 2: Synthesis of 1,3-dibromo-5-(3-bromobenzyl)benzene

[0433] OH

[0434]

[0435] (3-Bromophenyl)(3,5-dibromophenyl)methanol (step 1, 2.84 g, 6.7 mmol) was dissolved in 20 mL of dichloromethane. Triethylsilane (Merck, CAS: 617-86-7, 3.16 g, 27 mmol) was added, and the mixture was cooled to 0 °C. Trifluoromethanesulfonic acid (Merck, CAS: 1493-13-6, 4.0 g, 27 mmol) was added dropwise, and the mixture was stirred at room temperature for 3 hours. After this period, the reaction was quenched with deionized water 15

[0436] (20 g). The organic layer was washed several times with water and a 5% sodium bicarbonate solution. Subsequently, the solvent was removed under vacuum at 40 °C, yielding a brownish solid weighing 5.5 g. The crude product was purified via crystallization in n-heptane, resulting 1.8 g (64 %) as colorless solid.

[0437] 201H NMR (500 MHz, Chloroform-d) 5 = 7.55 (t, J = 1.8 Hz, 1 H), 7.40 (dt, J = 8.1, 1.4 Hz, 1H), 7.33 (t, J = 1.9 Hz, 1H), 7.27 (d, J = 1.7 Hz, 2H), 7.21 (t, J = 7.8 Hz, 1 H), 7.11 (dt, J = 7.7, 1.4 Hz, 1 H), 3.90 (s, 2H) ppm.

[0438] Step 3: Synthesis of 1,3-divinyl-5-(3-vinylbenzyl)benzene

[0439]

[0440] The protocol followed the synthesis described in Example 1 , step 3, using 1 ,3-dibromo-5-(3-bromobenzyl)benzene (step 2, 30 g, 74 mmol), which resulted in 12 g (66 %) of the desired product as colorless liquid.

[0441] 301H NMR (500 MHz, Chloroform-d): 5 = 7.42 (t, J = 1.7 Hz, 1 H), 7.40 - 7.35 (m, 1H), 7.38 - 7.31 (m, 2H), 7.24 (d, J = 1.6 Hz, 2H), 7.19 (dt, J = 7.5, 1.6Foreignfiling text P25-161.docx

[0442] - 41 -

[0443] Hz, 1 H), 6.79 (ddd, J = 17.7, 10.9, 3.8 Hz, 3H), 5.84 (ddd, J = 17.6, 4.9, 1.0 Hz, 3H), 5.33 (ddd, J = 10.9, 5.6, 0.9 Hz, 3H), 4.06 (s, 2H) ppm.

[0444] Example 5 (prior art): bis(4-vinylphenyl)methane

[0445] 5

[0446] Step 1: Synthesis of 1,3-dibromo-5-(3-bromobenzyl)benzene

[0447] HCT X^TX X \ZI'.W DMAp TfO X^ j-X X 'XX'-CTI

[0448]

[0449] DCM

[0450] Bis(4-hydroxyphenyl)methane (abcr, CAS: 620-92-8, 15 g, 74.9 mmol) was dissolved in 220 mL of dichloromethane (DCM) and treated with triethylamine (Merck, 29.1 mL, 210 mmol, 2.8 eq) and DMAP (Merck, 366 mg, 3 mmol, 0.04 eq). The reaction mixture was cooled to 5 °C and carefully treated dropwise with trifluoromethanesulfonic anhydride (Merck, 15 27.6 mL, 160 mmol, 2.2 eq). The mixture was then stirred at room temperature overnight. Following this, the reaction was quenched carefully with water at -10 °C. The phases were separated, and the organic phase was washed twice with water, dried over Na2SO4, and evaporated to remove the solvent. The crude product was purified by passing it through a silica plug with DCM as the eluent, yielding 32 g (92%) of a colorless oil. 20

[0451] 1H NMR (500 MHz, THF-cfe) 5 = 7.39 - 7.28 (m, 8H), 4.08 (s, 2H) ppm.

[0452] Step 2: Synthesis of bis(4-vinylphenyl)methane

[0453] K2CO3

[0454]

[0455] dioxane / H2O Methylenebis(4,1-phenylene)bis(trifluoromethanesulfonate) (32 g, 68.9 mmol) was dissolved alongside vinylboronic acid pinacol ester (abcr, CAS: 75927-49-0, 27.6 g, 179 mmol, 2.6 eq) and K2CO3 (413 mmol, 6 eq) in 680 mL of a 1 ,4-dioxane / water mixture (4:1 ). The reaction mixture was purged 30

[0456] with nitrogen for 15 minutes, after which Pd(PPh3)4 (Merck, CAS: 14221-01- 3, 9.6 g, 8.3 mmol, 0.1 eq) was added. The mixture was then heated toForeignfiling text P25-161.docx

[0457] -42 -

[0458] 80 °C for 2 hours, cooled to room temperature, and treated with water and MTBE. The phases were separated, and the aqueous phase was extracted with MTBE. The combined organic phases were washed three times with water, dried over Na2SO4, filtered, and the solvent was removed under vacuum. The crude product was finally purified by column chromatography 5

[0459] using silica gel with heptane as the eluent, resulting in 10 g (66%) of a colorless liquid.

[0460] 1H NMR (500 MHz, TF-c / 8): 5 = 7.34 - 7.29 (m, 4H), 7.12 (d, J = 8.1 Hz, 4H), 6.67 (dd, J = 17.6, 10.9 Hz, 2H), 5.69 (dd, J = 17.6, 1.1 Hz, 2H), 5.13 (dd, J = 10.8, 1.1 Hz, 2H), 3.92 (s, 2H) ppm.

[0461] Part B: Preparing of Photocurable Compositions with Vinyldiphenylethylene Compounds and Examining Key Material Properties

[0462] Photocurable compositions were prepared using at least one vinyldiphenylethylene compound from the present invention. The

[0463] 15 compositions contain also photoinitiators such as Omnirad 651 (Merck, CAS: 24650-42-8), Omnirad 1316 (IGM Resins, CAS: 2417522-91-7) or Irgacure OXE-02 (Boc Sciences, CAS: 478556-66-0).

[0464] Thermal Stability of Photo-Cured Layers

[0465] Photo-cured films were prepared by applying a 60 pm thick layer of 20 photocurable composition between two glass slides. The films were cured at room temperature using UV light with a wavelength of 365 nm, under varying curing energies. Following UV curing, the films may have been baked at 250 °C or 300 °C for 2 minutes on a hotplate and subsequently measured using TGA (TA Discovery).

[0466] The thermal stability of the composition can be assessed through a) monitoring weight loss up to 500 °C or b) determining the weight loss percentage per minute at different temperatures using an isothermal baking test, where the sample is heated to a predetermined temperature over 20 minutes and held at that temperature for 60 minutes.

[0467] 30 Comparison Study on Thermal Stability 1:

[0468] Formulations were prepared containing either a) 10 wt% of compound Example 2 (W.E. 1) or b) 10 wt% of compound Example 5 in compoundForeignfiling text P25-161.docx

[0469] -43 -

[0470] Example 4 (W.E. 2), along with 3 wt% of the photoinitiator Irgacure OXE- 02. These formulations were cured at room temperature at a wavelength of 365 nm, employing a curing energy of 10 J / cm2followed by a baking process at 250 °C for 2 minutes. The resulting polymers were then analyzed using an isothermal baking test conducted at 400 °C for 60 5

[0471] minutes (see Table 1 and Fig. 1).

[0472] Weight Example 2 Example 4 Example 5 loss% / m inute at 400 °C W.E. 1 10 wt% 90 wt% - 0.14% / min W.E. 2 - 90 wt% 10 wt% 0.50% / min

[0473]

[0474] TABLE 1. Weight loss per minute values for W.E. 1 and W.E. 2, both kept at 400 °C for 60 minutes. Each formulation includes 3 wt% of the photoinitiator Irgacure OXE-02.

[0475] Comparison Study on Thermal Stability 2:

[0476] Formulations were prepared as follows: a) W.E. 3 contained 25 wt% of Example 1 and 75 wt% of Example 4; b) W.E. 4 comprised 50 wt% of Example 1 and 50 wt% of Example 4; and c) W.E. 5 consisted of 100 wt% of Example 4, with all formulations including 1.5 wt% of the photoinitiator Omnirad 1316 and 4.0 wt% of Omnirad 651. These formulations were cured at room temperature at a wavelength of 365 nm with a curing energy of 10 J / cm2, followed by a baking process at 250 °C for 2 minutes. The resulting polymers were analyzed for a) material loss up to 500 °C and b) an isothermal baking test conducted at 425 °C for 60 minutes (see Table 2 and Figures 2 & 3).

[0477] Weight Material loss

[0478] Example 1 Example 4 loss% / m inute up to 500 °C

[0479] at 425 °C W.E. 3 25 wt% 75 wt% 32% 0.38 % / min 30 W.E. 4 50 wt% 50 wt% 22% 0.36 % / min W.E. 5 - 100 wt% 41% 0.67 % / min

[0480]

[0481] Foreignfiling text P25-161.docx

[0482] -44 -

[0483] TABLE 2. Material loss up to 500 °C and weight loss per minute values for W.E. 3, W.E. 4 and W.E. 5. All formulations included 1.5 wt% of the photoinitiator Omnirad 1316 and 4.0 wt% of Omnirad 651.

[0484] Comparison Study on Thermal Stability 3:

[0485] 5

[0486] Formulations were prepared as follows: a) W.E. 6 contained 10 wt% of Example 1 and 90 wt% of Example 4; b) W.E. 7 comprised 50 wt% of Example 1 and 50 wt% of Example 4; and c) W.E. 8 consisted of 100 wt% of Example 4, with all formulations including 1.5 wt% of the photoinitiator Omnirad 1316 and 4.0 wt% of Omnirad 651. These formulations were cured at room temperature at a wavelength of 365 nm with a curing energy of 5 J / cm2, followed by a baking process at 300 °C for 2 minutes. The resulting polymers were analyzed for a) material loss up to 500 °C and b) an isothermal baking test conducted at 425 °C for 60 minutes (see Table 3 and Figures 4 & 5).

[0487] Weight Material loss

[0488] Example 1 Example 4 loss% / m inute up to 500 °C

[0489] at 425 °C W.E. 6 10 wt% 90 wt% 38% 0.56% / min W.E. 7 50 wt% 50 wt% 30% 0.46% / min W.E. 8 - 100 wt% 42% 0.60% / min

[0490]

[0491] TABLE 3. Material loss up to 500 °C and weight loss per minute values for W.E. 6, W.E. 7 and W.E. 8. All formulations included 1.5 wt% of the photoinitiator Omnirad 1316 and 4.0 wt% of Omnirad 651.

[0492] 30

Claims

Foreignfiling text P25-161.docxPatent Claims1. A curable composition comprising a polymerization initiator and a compound of formula (1 ),5Formula (1)wherein the following applies to the symbols and indices used:R1is the same or different at each occurrence and is H or CH3;15R2is the same or different at each occurrence and is an alkyl group having 1 to 10 carbon atoms which can be substituted by one or more F atoms or an aromatic ring system having 6 to 12 aromatic ring atoms which can be substituted by one or more F atoms and / or alkyl groups having 1 to 10 C atoms;20n is 1 , 2 or 3;m is 0, 1 , 2 or 3;o is 0, 1 , 2, 3 or 4, with the proviso that n + o < 5;p is 0, 1 , 2, 3, 4 or 5, with the proviso that m + p < 5.

2. Composition according to claim 1 , characterized in that the compound of formula (1) is a compound of formula (2),Foreignfiling text P25-161.docx5Formula (2)where the symbols and indices have the same meanings as described in claim 1.

3. Composition according to claim 1 or 2, characterized in that the compound of formula (1) is selected from the compounds of formulae (3), (4) and (5),Formula (5)wherein the symbols and indices have the same meanings as defined in claim 1 and q and r are each independently 0 or 1.

4. Composition according to one or more of claims 1 to 3, characterized in that the compound of formula (1 ) is a compound of formula (2b), 30Foreignfiling text P25-161.docx-47 -5 Formula (2b)where the symbols and indices have the same meanings as described in claim 1.

5. Composition according to one or more of claims 1 to 4, characterized in that the compound of formula (1) is selected from the compounds of formula (3c), (4c) and (5c),Formula (4c)Formula (5c)wherein q and r are each independently 0 or 1.

6. Composition according to one or more of claims 1 to 5, characterized in that it comprises at least one further polymerizable compound.30 7. Composition according to claim 6, characterized in that the further polymerizable compound is a compound represented by formula (M1),Foreignfiling text P25-161.docx-48 -Formula (M1)5wherein the following applies to the symbols and indices:X is the same or different at each occurrence and is selected from -L2-CR4=C(R4)2or -L2-C=CR4;L1is a single bond, 0, C(=0), a linear alkylene group having 1 to 10 carbon atoms or a branched or cyclic alkylene group having 3 to 10 carbon atoms wherein the linear, branched or cyclic alkylene group can be substituted by one or more F atoms and wherein one or more non-adjacent C atoms of the alkylene group can be replaced by 0;L2is the same or different at each occurrence and is a single bond, a linear alkylene group having 1 to 10 carbon atoms or a branched or cyclic alkylene group having 3 to 10 carbon atoms wherein the linear, branched or cyclic alkylene group can be substituted by one or more F atoms and wherein one or more non-adjacent C atoms of the alkylene group can be replaced by 0;R3is the same or different at each occurrence and is a linear alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms wherein the linear, branched or cyclic alkyl group can be substituted by one or more F atoms, OH or COOH and wherein one or more non-adjacent C atoms of the alkyl group can be replaced by 0;R4is the same or different at each occurrence and is H, a linear alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl 30 group having 3 to 10 carbon atoms; herein the linear, branched or cyclic alkyl group can be substituted by one or more F atoms, OHForeignfiling text P25-161.docx-49 -or COOH and wherein one or more non-adjacent C atoms of the alkyl group can be replaced by 0w is 0 or 1 , where for w = 0 either H or a group X or a group R3is bound instead of L1;5s is 1 , 2, 3 or 4;t is 0, 1, 2, 3 or 4;u, v is the same or different at each occurrence and is 0, 1 , 2, 3 or 4, with the proviso that s + u + w < 6 and v + t < 5.

8. Composition according to claim 7, wherein the following applies to the symbols and indices:15 X is the same or different at each occurrence and is a group of formula -L2-CR4=C(R4)2;L1is a single bond, a linear alkylene group having 1 to 5 carbon atoms or a branched alkylene group having 3 to 5 carbon atoms; and particularly preferably a single bond, methylene or ethylene;20L2is a single bond, a linear alkylene group having 1 to 5 carbon atoms or a branched alkylene group having 3 to 5 carbon atoms; and particularly preferably a single bond, methylene or ethylene;R3is the same or different at each occurrence and is a linear alkyl group having 1 to 5 carbon atoms or a branched or cyclic alkyl group having 3 to 5 carbon atoms; preferably methyl, ethyl, n- propyl, i-propy I, n-butyl, sec-butyl, i-butyl or t-butyl, and particularly preferably methyl;30 R4is the same or different at each occurrence and is H, a linear alkyl group having 1 to 5 carbon atoms or a branched alkyl group havingForeignfiling text P25-161.docx- 50 -3 to 5 carbon atoms; and more preferably H or methyl and most preferably H;w is 1 ;5s is 1 , 2 or 3, preferably 1 or 2;t is 0, 1 , 2 or 3, preferably 0, 1 or 2 and more preferably 1 or 2;u, v is the same or different at each occurrence and is 0, 1 or 2, preferably 0 or 1 and more preferably 0.

9. Composition according to one or more of claims 1 to 8, characterized in that the total amount of the compound of formula (1 ) is in the range from 5 to 99 wt% based on the total amount of the composition, preferably from 10 to 90 wt%, more preferably from 10 to 80 wt%, and 15 most preferably 20 to 50 wt%, and that the amount of the second polymerizable compound, if present, is in the range from 10 to 90 wt%, preferably 20 to 80 wt%, more preferably 30 to 70 wt% based on the total amount of polymerizable compounds in the composition.

10. Composition according to one or more of claims 1 to 9, characterized in 20 that the composition is a photo-curable composition and the polymerization initiator is a photo-radical initiator which is present in a content in the range from 0.5 to 10 wt%, based on the composition.

11. Composition according to one or more of claims 1 to 10, characterized in that the composition comprises at least one further component, selected from one or more solvents, surfactants, adhesion promoters, corrosion resistance additives, crosslinking agents, dispersants, fillers, pigments, nanoparticles, particles that reduce thermal expansion, polymerization inhibitors, rheology modifiers, and / or adhesion enhancers.30Foreignfiling text P25-161.docx- 51 -12. Composition according to one or more of claims 1 to 11 , characterized in that the viscosity of the composition at 23 °C is in the range from 2 to 100 cP, preferably from 2 to 50 cP, more preferably from 5 to 20 cP.

13. Method for preparing a composition according to one or more of claims 51 to 12, comprising a step of mixing a compound according to formula (1) and a polymerization initiator.

14. Use of a composition according to one or more of claims 1 to 12 in an inkjet adaptive planarization process.

15. Method for preparing a cured layer, comprising the following steps in the following order:(i) forming a layer of the composition according to one or more of claims 1 to 12 on a substrate;(ii) optionally bringing the layer into contact with a template;15 (iii) curing the composition by heat and / or by irradiation of the layer with light to form a cured layer;(iv) optionally removing the template from the cured layer.

16. Method for manufacturing a device comprising the following steps:(i) forming a cured film by the method according to claim 15;20 (ii) processing the substrate.

17. Cured layer obtainable by a method according to claim 15.

18. Compound represented by formula (T),30Formula (1’)Foreignfiling text P25-161.docx- 52 -wherein the following applies to the symbols and indices used:R1is the same or different at each occurrence and is H or CH3;R2is the same or different at each occurrence and is an alkyl group 5having 1 to 10 carbon atoms which can be substituted by one or more F atoms or an aromatic ring system having 6 to 12 aromatic ring atoms which can be substituted by one or more F atoms and / or alkyl groups having 1 to 10 C atoms;n is 1 , 2 or 3;m is 0, 1 , 2 or 3;with the proviso that n + m > 2;15 o is 0, 1 , 2, 3 or 4, with the proviso that n + o < 5;p is 0, 1 , 2, 3, 4 or 5, with the proviso that m + p < 5.2030

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