KR20230160168A - Polysiloxane compound, Coating film forming composition, Layered body, Touch Panel and Method for forming cured coating film - Google Patents

Abstract

[Problem] To provide a polysiloxane-based compound that can obtain a cured film with excellent tackiness and also has excellent developability and photocurability.
[Solution] A structural unit (A) derived from a silane-based compound (A) that is at least one type selected from the group of tetraalkoxysilane and bis(trialkoxysilyl)alkane, alkyltrialkoxysilane, dialkyldialkoxysilane, cyclo A silane-based compound having a structural unit (B) derived from at least one silane-based compound (B) selected from the group of alkyltrialkoxysilane, vinyltrialkoxysilane, and phenyltrialkoxysilane, and a radically polymerizable unsaturated double bond. A polysiloxane-based compound containing at least a structural unit (C) derived from (C) and having a structural ratio calculated by the following formula (1) greater than 0 and less than 0.1.

(In formula (1), MA represents the number of moles of the structural unit (A), MB represents the number of moles of the structural unit (B), and MC represents the number of moles of the structural unit (C).)

Description

Polysiloxane compound, coating film forming composition, laminate, touch panel, and method for forming a cured coating {Polysiloxane compound, coating film forming composition, Layered body, Touch Panel and Method for forming cured coating film}

The present invention relates to a polysiloxane-based compound, a composition for forming a film, a laminate, a touch panel, and a method of forming a cured film.

Polysiloxane-based compounds are used as compositions for forming films that form insulating layers used in sensor parts of electronic components such as touch panels, LEDs, and semiconductors used in smartphones and tablet-type PCs.

For example, Patent Document 1 discloses a resin composition for a white LED sealant containing 0.5 to 10 parts by mass of a radical initiator per 100 parts by mass of polysiloxane having a (meth)acryloyl group.

Polysiloxane-based compounds have tackiness after prebaking, and when used in touch panels, etc., the substrate and mask adhere to each other during contact exposure, resulting in poor workability during processing.

On the other hand, a method called proximity exposure in which a gap is provided to prevent damage to the substrate and mask is used, but it has the disadvantage that the resolution is lowered due to the gap.

In the method described in Patent Document 1, the tackiness (property to suppress tackiness) was still insufficient, and there was room for further improvement.

Additionally, the photolithography method is mainly used to form electrode layers and insulating layers used in electronic components, etc.

Therefore, during the development process, the exposed portion irradiated with active energy rays has the property (also known as photocurability) of not being removed by the developer, while the unexposed portion shielded from the active energy ray has the property of being quickly dissolved and removed by the developer (also known as photocurability). (also known as development) was required.

[Patent Document 1] Japanese Patent Publication No. 2008-131009

Therefore, the purpose of the present invention is to provide a polysiloxane-based compound that can obtain a cured film with excellent tackiness and also has excellent developability and photocurability.

The present inventor has carefully studied polysiloxane-based compounds and discovered that a polysiloxane-based compound capable of solving all of the above problems can be obtained by having structural units derived from a specific siloxane-based compound in a predetermined molar ratio.

That is, the present invention includes a structural unit (A) derived from a silane-based compound (A) that is at least one selected from the group of tetraalkoxysilane and bis(trialkoxysilyl)alkane, alkyltrialkoxysilane, and dialkyldialkoxysilane. , a silane-based structural unit (B) derived from at least one silane-based compound (B) selected from the group of cycloalkyltrialkoxysilane, vinyltrialkoxysilane, and phenyltrialkoxysilane, and a radically polymerizable unsaturated double bond. It is a polysiloxane-based compound containing at least a structural unit (C) derived from the compound (C) and having a structural ratio calculated by the following formula (1) greater than 0 and less than 0.1.

(In formula (1), MA represents the number of moles of the structural unit (A), MB represents the number of moles of the structural unit (B), and MC represents the number of moles of the structural unit (C).)

In the polysiloxane-based compound of the present invention, the silane-based compound (A) is preferably tetraethoxysilane.

Additionally, the silane-based compound (B) is preferably phenyltrimethoxysilane and/or methyltriethoxysilane.

Additionally, the silane-based compound (C) is preferably 3-(methacryloyloxy)propyltrimethoxysilane.

In addition, it is preferable that the composition ratio calculated by the above formula (1) is 0.03 or more and 0.08 or less.

The present invention is also a composition for forming a film containing at least the polysiloxane-based compound, a radical photopolymerization initiator, and an organic solvent.

In the composition for forming a film of the present invention, it is preferable that the radical photopolymerization initiator contains a ketoxime ester group.

The present invention is also a laminate formed by coating the above film-forming composition.

Additionally, the present invention is also a touch panel made using the above laminate.

In addition, the present invention is characterized in that it has a process of applying the composition for forming a film, an exposure process of forming a cured film by irradiating active energy rays to the exposed area, and a development process of dissolving and removing the coating solution in the unexposed area with a developing solution. It is also a method of forming a hardened film.

A polysiloxane-based compound capable of obtaining a cured film with excellent tackiness and also excellent in developability and photocurability is provided.

<Polysiloxane-based compound>

The polysiloxane-based compound of the present invention includes a structural unit (A) derived from a silane-based compound (A) that is at least one type selected from the group of tetraalkoxysilane and bis(trialkoxysilyl)alkane, an alkyltrialkoxysilane, and a dialkyldi. It has a structural unit (B) derived from a silane-based compound (B) that is at least one type selected from the group of alkoxysilanes, cycloalkyltrialkoxysilanes, vinyltrialkoxysilanes, and phenyltrialkoxysilanes, and a radically polymerizable unsaturated double bond. It contains at least a structural unit (C) derived from a silane-based compound (C), and the structural ratio calculated by the following formula (1) is greater than 0 and less than 0.1. .

(In formula (1), MA represents the number of moles of the structural unit (A), MB represents the number of moles of the structural unit (B), and MC represents the number of moles of the structural unit (C).)

[Silane compound (A)]

The polysiloxane-based compound of the present invention contains a structural unit (A) derived from at least one silane-based compound (A) selected from the group of tetraalkoxysilane and bis(trialkoxysilyl)alkane.

The silane-based compound (A) is at least one selected from the group of tetraalkoxysilane and bis(trialkoxysilyl)alkane.

Examples of the tetraalkoxysilane include tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetraisopropoxysilane, tetra-n-butoxysilane, tetraisobutoxysilane, ethoxytrimethoxysilane, di Methoxydiethoxysilane, methoxytriethoxysilane, etc. are mentioned.

Examples of the bis(trialkoxysilyl)alkanes include bis(trimethoxysilyl)methane, bis(triethoxysilyl)methane, 1,2-bis(trimethoxysilyl)ethane, and 1,2-bis(triethoxysilyl). )Ethane, etc. may be mentioned.

In terms of versatility, the silane-based compound (A) includes tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetraisopropoxysilane, tetra-n-butoxysilane, tetraisobutoxysilane, and bis. (Triethoxysilyl)methane and 1,2-bis(triethoxysilyl)ethane are preferable, tetramethoxysilane, tetraethoxysilane, and tetraisopropoxysilane are more preferable, and tetraethoxysilane is still more preferable. desirable.

[Silane compound (B)]

The polysiloxane-based compound of the present invention is derived from at least one silane-based compound (B) selected from the group of alkyltrialkoxysilane, dialkyldialkoxysilane, cycloalkyltrialkoxysilane, vinyltrialkoxysilane, and phenyltrialkoxysilane. Contains structural unit (B).

Examples of the alkyl trialkoxysilane include methyltrimethoxysilane, methyltriethoxysilane, methyltri-n-propoxysilane, methyltriisopropoxysilane, methyltri-n-butoxysilane, methyltriisobutoxysilane, and methyltriisobutoxysilane. Tri-sec-butoxysilane, methyltri-tert-butoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, ethyltri-n-propoxysilane, ethyltriisopropoxysilane, ethyltri-n- Butoxysilane, ethyltriisobutoxysilane, n-propyltrimethoxysilane, n-propyltriethoxysilane, n-propyltri-n-propoxysilane, n-propyltriisopropoxysilane, n-propyltri -n-butoxysilane, n-propyltriisobutoxysilane, n-propyltri-sec-butoxysilane, n-propyltri-tert-butoxysilane, isopropyltrimethoxysilane, isopropyltriethoxysilane , Isopropyltri-n-propoxysilane, Isopropyltriisopropoxysilane, Isopropyltri-n-butoxysilane, Isopropyltriisobutoxysilane, Isopropyltri-sec-butoxysilane, Isopropyltri- tert-butoxysilane, etc. can be mentioned.

Examples of the dialkyl dialkoxysilanes include dimethyldimethoxysilane, dimethyldiethoxysilane, dimethyldi-n-propoxysilane, dimethyldiisopropoxysilane, dimethyldi-n-butoxysilane, dimethyldiisobutoxysilane, and dimethyldimethylsilane. -sec-butoxysilane, dimethyldi-tert-butoxysilane, diethyldimethoxysilane, diethyldiethoxysilane, diethyldi-n-propoxysilane, diethyldiisopropoxysilane, diethyldi- n-butoxysilane, diethyldiisobutoxysilane, diethyldi-sec-butoxysilane, diethyldi-tert-butoxysilane, di-n-propyldimethoxysilane, di-n-propyldiethoxysilane , di-n-propyldi-n-propoxysilane, di-n-propyldiisopropoxysilane, di-n-propyldi-n-butoxysilane, di-n-propyldiisobutoxysilane, di- n-propyldi-sec-butoxysilane, di-n-propyldi-tert-butoxysilane, diisopropyldimethoxysilane, diisopropyldiethoxysilane, diisopropyldi-n-propoxysilane, di Isopropyl diisopropoxysilane, diisopropyl di-n-butoxysilane, diisopropyl diisobutoxysilane, diisopropyl di-sec-butoxysilane, diisopropyl di-tert-butoxysilane, di -n-butyldimethoxysilane, di-n-butyldiethoxysilane, di-n-butyldi-n-propoxysilane, di-n-butyldiisopropoxysilane, di-n-butyldi-n- Butoxysilane, di-n-butyldiisobutoxysilane, di-n-butyldi-sec-butoxysilane, di-n-butyldi-tert-butoxysilane, diisobutyldimethoxysilane, diisobutyl Diethoxysilane, diisobutyldi-n-propoxysilane, diisobutyldiisopropoxysilane, diisobutyldi-n-butoxysilane, diisobutyldiisobutoxysilane, diisobutyldi-sec- Butoxysilane, diisobutyldi-tert-butoxysilane, di-sec-butyldimethoxysilane, di-sec-butyldiethoxysilane, di-sec-butyldi-n-propoxysilane, di-sec- Butyldiisopropoxysilane, di-sec-butyldi-n-butoxysilane, di-sec-butyldiisobutoxysilane, di-sec-butyldi-sec-butoxysilane, di-sec-butyldi- tert-butoxysilane, di-tert-butyldimethoxysilane, di-tert-butyldiethoxysilane, di-tert-butyldi-n-propoxysilane, di-tert-butyldiisopropoxysilane, di- tert-butyldi-n-butoxysilane, di-tert-butyldiisobutoxysilane, di-tert-butyldi-sec-butoxysilane, di-tert-butyldi-tert-butoxysilane, etc. there is.

Examples of the cycloalkyltrialkoxysilanes include cyclopentyltrimethoxysilane, cyclopentyltriethoxysilane, cyclopentyltri-n-propoxysilane, cyclopentyltriisopropoxysilane, and cyclopentyltri-n-butoxysilane. Silane, cyclopentyltriisobutoxysilane, cyclopentyltri-sec-butoxysilane, cyclopentyltri-sec-butoxysilane, cyclohexyltrimethoxysilane, cyclohexyltriethoxysilane, cyclohexyltri- n-propoxysilane, cyclohexyltriisopropoxysilane, cyclohexyltri-n-butoxysilane, cyclohexyltriisobutoxysilane, cyclohexyltri-sec-butoxysilane, cyclohexyltri-tert-butoxysilane etc. can be mentioned.

Examples of the vinyl trialkoxysilane include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltri-n-propoxysilane, vinyltriisopropoxysilane, vinyltri-n-butoxysilane, vinyltriisobutoxysilane, vinyl Tri-sec-butoxysilane, vinyltri-tert-butoxy silane, etc. may be mentioned.

Examples of the phenyltrialkoxysilane include phenyltrimethoxysilane, phenyltriethoxysilane, phenyltri-n-propoxysilane, phenyltriisopropoxysilane, phenyltri-n-butoxysilane, phenyltriisobutoxysilane, and phenyltriisopropoxysilane. Tri-sec-butoxysilane, phenyltri-tert-butoxysilane, etc. may be mentioned.

The silane-based compound (B) is preferably at least one selected from the group of methyltriethoxysilane, dimethyldimethoxysilane, cyclohexyltriethoxysilane, vinyltrimethoxysilane, and phenyltrimethoxysilane, and phenyl Trimethoxysilane and/or methyltriethoxysilane are more preferred.

[Silane compound (C)]

The polysiloxane-based compound of the present invention contains at least a structural unit (C) derived from a silane-based compound (C) having a radically polymerizable unsaturated double bond.

Examples of the silane-based compound (C) include (3-(meth)acryloyloxy)propylmethyldimethoxysilane, (3-(meth)acryloyloxy)propyltrimethoxysilane, and (3-(meth)acryloyloxy)propyltrimethoxysilane. (3-(meth)acryloyloxy)propylsilane compounds such as yloxy)propylethyldiethoxysilane, (3-(meth)acryloyloxy)propyltriethoxysilane, allyltrimethoxysilane, allyltri Allylsilane compounds such as ethoxysilane can be mentioned.

Among them, (3-(meth)acryloyloxy)propyltrimethoxysilane is preferable from the viewpoint of the balance between developability and stability of maintaining the pattern shape of the cured film.

[Other silane compounds (D)]

As the silane-based compound before condensation constituting the polysiloxane-based compound, for example, a silane-based compound having an epoxy group in the molecule may be added as needed.

Here, the silane-based compounds having an epoxy group in the molecule include (3-glycidoxypropyl)trimethoxysilane, (3-glycidoxypropyl)methyldimethoxysilane, and (3-glycidoxypropyl)triethoxysilane. , (3-glycidoxypropyl)methyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, (2 -(3,4-epoxycyclohexyl)ethyl)methyldimethoxysilane, (2-(3,4-epoxycyclohexyl)ethyl)methyldiethoxysilane, etc.

[Composition ratio]

The polysiloxane-based compound of the present invention has a composition ratio calculated by the following formula (1) greater than 0 and less than 0.1.

If the composition ratio is within the above range, tackiness of the cured film can be suppressed, and a polysiloxane-based compound excellent in developability and photocurability can be obtained.

It is preferable that the composition ratio calculated by the following formula (1) is 0.03 or more and 0.08 or less.

(In formula (1), MA represents the number of moles of the structural unit (A), MB represents the number of moles of the structural unit (B), and MC represents the number of moles of the structural unit (C).)

The molar ratio of the structural unit (A) derived from the silane-based compound (A) to all the structural units forming the polysiloxane-based compound is determined by coating the film-forming composition of the present invention by photolithography to form a cured film. From the viewpoint of increasing the developability of the non-photocured portion of the unexposed portion and the photocured portion of the exposed portion, it is preferably 0.10 to 0.25, and more preferably 0.15 to 0.22.

The molar ratio of the structural unit (B) derived from the silane-based compound (B) to all the structural units forming the polysiloxane-based compound is determined by coating the film-forming composition of the present invention by photolithography to form a cured film. From the viewpoint of lowering the developability of the non-photocured portion of the unexposed portion and the photocured portion of the exposed portion, it is preferably 0.65 to 0.90, and more preferably 0.70 to 0.85.

The molar ratio of the structural unit (C) derived from the silane-based compound (C) to all the structural units forming the polysiloxane-based compound is preferably 0.020 to 0.10, and 0.025 to 0.075 from the viewpoint of photocurability and tackiness. It is more desirable.

The molar ratio of the structural unit (D) derived from the silane-based compound (D) to all the structural units forming the polysiloxane-based compound is determined by the developability of the unexposed area and the non-photocured area, as well as the cured film and the substrate or ITO. From the viewpoint of adhesion to the electrode, it is preferable that it is 0 to 0.005, and it is more preferable that it is 0 to 0.002.

[Method for producing polysiloxane-based compounds]

A method for producing the polysiloxane-based compound will be described.

As a method for producing the polysiloxane-based compound, for example, the silane-based compounds (A) to (C) and optionally other silane-based compounds (D) are mixed in an appropriate container, followed by mixing water, a polymerization catalyst, and the necessary ingredients. Accordingly, a method of hydrolyzing and condensing by adding a reaction solvent may be used.

Here, the amount of water is preferably such that the number of water molecules is equal to the number of all hydrolyzable substituents of the silane-based compound added into the container.

Since the silane-based compound has 3 or 4 hydrolyzable substituents per molecule, when a large amount of such silane-based compound is contained, the amount of water is simply calculated as the number of water molecules for the number of all molecules of the silane-based compound added into the container. The number may be 3 to 4 times (as a molar ratio, the total amount of silane-based compound: water = 1:3 to 4).

As the polymerization catalyst, for example, an acid catalyst such as acetic acid or hydrochloric acid, or a base catalyst such as ammonia, triethylamine, cyclohexylamine, or tetramethylammonium hydroxide can be used. And, as the amount of polymerization catalyst, the number of polymerization catalyst molecules is 0.05 to 0.2 times the number of all molecules of the silane-based compound introduced into the container (as a molar ratio, the total amount of silane-based compound: polymerization catalyst = 1: 0.05 to 0.2). An amount equal to is desirable.

Preferred reaction solvents include lower alcohols such as ethanol, n-propyl alcohol, and isopropyl alcohol, ketone compounds such as acetone and methyl ethyl ketone, and ester compounds such as ethyl acetate and n-propyl acetate. Among these, lower alcohols are preferred. Ethanol and isopropyl alcohol are more preferable because they can maintain an appropriate reaction temperature and are easy to distill.

The reaction temperature is preferably 60 to 80°C, and the reaction time is preferably 2 to 24 hours to ensure that the reaction sufficiently progresses.

After the reaction, unnecessary by-products other than the polysiloxane-based compound can be removed by extraction, dehydration, solvent removal, etc. to obtain the polysiloxane-based compound.

[Physical properties of polysiloxane compounds]

The polysiloxane-based compound of the present invention has excellent tackiness (can suppress tackiness).

The tackiness can be judged by the following test.

The polysiloxane-based compound was diluted with propylene glycol monomethyl acetate so that the concentration of the non-volatile component was 25% by mass, and a commercially available 50 mm horizontal and vertical coating was applied under the coating conditions of 400 rpm and 60 seconds using a spin coater (MS-A100, manufactured by Mikasa). A polysiloxane-based compound is applied to a square soda glass substrate.

Next, a test piece for evaluation is produced by heating (prebake) at 80°C for 3 minutes.

Touch the surface of the evaluation test piece coated with the polysiloxane-based compound with your finger to visually check the extent of the remaining traces. If no finger traces remain, it can be judged that the tackiness is excellent.

The polysiloxane-based compound of the present invention has excellent developability.

The developability can be judged by the following test.

The test piece for evaluation used in the above tackiness test is exposed to a 2.38% by mass aqueous solution (developer) of tetramethylammonium hydroxide, the state of dissolution is observed with the naked eye, and when complete dissolution is confirmed, it can be judged that the developability is excellent. .

The polysiloxane-based compound of the present invention has excellent photocurability.

The photocurability can be judged by the following test.

To 100 parts by mass of a polysiloxane-based compound, 2.5 parts by mass of Irgacure OXE02, 0.13 parts by mass of 4-methoxyphenol, and 0.6 parts by mass of BYK-310 were added to propylene glycol monomer so that the concentration of non-volatile component was 25%. It is diluted with methyl acetate and coated on a commercially available 50 mm square soda glass substrate using a spin coater (MS-A100, manufactured by Mikasa) under coating conditions of 400 rpm and 60 seconds.

Next, after heating (prebake) at 80°C for 3 minutes, the test pattern was baked using a mask aligner (PLA-501FA, manufactured by Canon) under irradiation conditions of 100 mJ/cm2, and a portion of it was used as a developer. After being immersed in a 2.38% by mass aqueous solution (developer) of tetramethylammonium hydroxide for 1 minute, it is heated (post-baked) at 150°C for 30 minutes to produce a test piece for evaluation.

The film thickness (T1) of the exposed part of the part exposed to the developer and the film thickness (T2) of the unexposed part of the unexposed part were measured using a film thickness measuring device (Alpha-Step IQ surface profiler, manufactured by KLM-Tencor). When measured, if T1/T2 is 0.35 or more, photocurability can be judged to be excellent, and if T1/T2 is 0.55 or more, photocurability can be judged to be particularly excellent.

The polysiloxane-based compound of the present invention preferably has a weight average molecular weight (Mw) of 800 to 10,000.

If the weight average molecular weight (Mw) is less than 800, the curability of the film-forming composition may decrease, and if the weight average molecular weight (Mw) exceeds 10,000, the solubility of the film-forming composition may decrease.

The polysiloxane-based compound more preferably has a weight average molecular weight (Mw) of 1000 to 5000.

In addition, as the weight average molecular weight (Mw), the polysiloxane-based compound was dissolved to prepare a solution of 0.02% by mass, and passed through a filter (GL Science Disk, water system 25A, pore diameter 0.2 μm). Afterwards, it can be measured under the following conditions using a semi-micro GPC/SEC analysis system (manufactured by Nihon Spectrophotography) consisting of size exclusion chromatography and a refractive index detector.

Column: KF-603, KF-604 (all manufactured by Showa Denko) serial connection

RI detector: RI-4035 (manufactured by Nippon Spectroscope)

PDA detector: MD-4015 (manufactured by Nippon Spectroscope)

Eluent: THF

Flow rate: 1.0ml/min

Injection volume: 100μl

<Composition for film formation>

The composition for forming a film of the present invention contains at least the above-described polysiloxane-based compound, a radical photopolymerization initiator, and an organic solvent.

[Photo radical polymerization initiator]

Examples of the radical photopolymerization initiator include acylphosphine oxide-based compounds, thioxanthone-based compounds, aromatic ketones, aromatic onium salt compounds, organic peroxides, thiophene compounds (thiophenyl group-containing compounds, etc.), α-aminoalkylphenone compounds, Examples include hexaarylbiimidazole compounds, ketoxime ester compounds, borate compounds, azinium compounds, metallocene compounds, active ester compounds, compounds having a carbon halogen bond, and alkylamine compounds.

Among these, it is preferable to contain a ketoxime ester group from the viewpoint of increasing photocuring reactivity when forming a cured film by the photolithography method.

[Organic solvent]

As the organic solvent, organic solvents used as common coating agents, such as alcohols, polyhydric alcohols and their derivatives, ketone-based organic solvents, and ester-based organic solvents, can be used.

Here, as alcohols, lower alcohols such as methanol, ethanol, n-propyl alcohol-n-, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, and sec-butyl alcohol can be suitably used.

In addition, examples of polyhydric alcohols include ethylene glycol, propylene glycol, 1,2-butanediol, 1,3-butanediol, diethylene glycol, and dipropylene glycol.

In addition, as polyhydric alcohol derivatives, first of all, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol monoisopropyl ether, ethylene glycol mono-n-butyl ether, and ethylene glycol monoisobutyl ether. , ethylene glycol monophenyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol monoisopropyl ether, propylene glycol mono-n-butyl ether, propylene glycol monoisobutyl ether. , propylene glycol monophenyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol monoisopropyl ether, diethylene glycol mono-n-butyl ether, di Ethylene glycol monoisobutyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol-n-propyl ether, dipropylene glycol isopropyl ether, dipropylene glycol-n-butyl ether, dipropylene glycol iso Glycol monoethers such as butyl ether can be mentioned.

Furthermore, propylene glycol monomethyl acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monomethyl ether propionate, ethylene glycol monoethyl ether acetate, ethylene glycol mono-n-propyl ether acetate, ethylene glycol monoisopropyl ether acetate, ethylene Glycol mono-n-butyl ether acetate, ethylene glycol monoisobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol mono-n-propyl ether acetate, propylene glycol monoisopropyl ether acetate, propylene Glycol mono-n-butyl ether acetate, propylene glycol monoisobutyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol mono-n-propyl ether acetate, diethylene glycol monoisopropyl Ether acetate, Diethylene glycol mono-n-butyl ether acetate, Diethylene glycol monoisobutyl ether acetate, Dipropylene glycol monomethyl ether acetate, Dipropylene glycol monoethyl ether acetate, Dipropylene glycol mono-n-propyl ether acetate, Glycol monoether acylates such as dipropylene glycol monoisopropyl ether acetate, dipropylene glycol mono-n-butyl ether acetate, and dipropylene glycol monoisobutyl ether acetate can be mentioned.

Additionally, examples of the ketone-based organic solvent include acetone, methyl ethyl ketone, methyl-n-propyl ketone, methyl isopropyl ketone, methyl-n-butyl ketone, methyl isobutyl ketone, and cyclohexanone.

In addition, ester-based organic solvents include ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, n-amyl acetate, isoamyl acetate, methyl propionate, ethyl propionate, methyl lactate, Ethyl lactate, n-propyl lactate, etc. can be mentioned.

These organic solvents can be used individually or in combination of two or more types. In view of the solubility and coating suitability of polysiloxane compounds, polyhydric alcohol derivatives and ester organic solvents are preferable, especially propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, and propylene glycol. Monoisopropyl ether, propylene glycol mono-n-butyl ether, propylene glycol monoisobutyl ether, propylene glycol monomethyl acetate, propylene glycol monomethyl ether acetate, n-propyl acetate, and isopropyl acetate are preferred.

[Polymerizable monomer]

The composition for forming a film of the present invention may contain a polymerizable monomer.

Examples of the polymerizable monomer include 1,3-butylene glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9 -Nonanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate Rate, tetraethylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetrapropylene glycol di(meth)acrylate, bisphenol A di(meth)acrylate , tris(2-hydroxyethyl)isocyanuric acid di(meth)acrylate, trimethylolpropane tri(meth)acrylate, glycerin tri(meth)acrylate, pentaerythritol tri(meth)acrylate, tris( 2-Hydroxyethyl)isocyanuric acid tri(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, di Pentaerythritol hexa(meth)acrylate, etc. can be mentioned.

Among them, compounds having three or more reactive functional groups from the viewpoint of providing appropriate hardness to the cured coating, such as trimethylolpropane tri(meth)acrylate, glycerin tri(meth)acrylate, and pentaerythritol tri(meth)acrylate. Acrylate, tris(2-hydroxyethyl)isocyanuric acid tri(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate Rate and dipentaerythritol hexa(meth)acrylate are preferable, and tris(2-hydroxyethyl)isocyanuric acid tri(meth)acrylate and dipentaerythritol hexa(meth)acrylate are more preferable.

[additive]

The composition for forming a film of the present invention is a chelate compound of a metal such as aluminum, zirconium, or titanium, a carbodiimide type, an isocyanate type, or a crosslinkable functional group such as an epoxy group or thiol group, within a range that does not reduce the effect of the present invention. Crosslinking agents, silicone-based, fluorine-based surfactants, aromatic hydrocarbon-based, amino compound-based, nitro compound-based, photosensitizers such as quinones and xanthone, hydroquinone, methoquinone, hindered amine-based, hindered phenol-based, -tert-Polymerization inhibitors such as butylhydroquinone, 4-methoxyphenol, butylhydroxytoluene, and nitrosamine salts, fillers such as inorganic metal oxides and organic fine particles, etc. may be added.

[Content of each material in film forming composition]

The polymerizable monomer is preferably contained in an amount of 10 to 50 parts by mass based on 100 parts by mass of the polysiloxane-based compound.

If the content of the polymerizable monomer is less than 10 parts by mass with respect to 100 parts by mass of the polysiloxane-based compound, the curability of the cured film or the adhesion to the glass substrate, etc. may become insufficient. If it exceeds it, the solubility of the uncured film in the developer may become insufficient.

The radical photopolymerization initiator is preferably contained in an amount of 0.5 to 40 parts by mass when the total amount of the polysiloxane-based compound and the polymerizable monomer is 100 parts by mass.

If the content of the radical photopolymerization initiator is less than 0.5 parts by mass, photopolymerizability may decrease and unreacted components may remain in the exposed area of the photolithography method, and if it exceeds 40 parts by mass, the storage stability of the composition for forming a film may decrease. There is a possibility.

The radical photopolymerization initiator is more preferably 1 to 20 parts by mass when the total amount of the polysiloxane-based compound and the polymerizable monomer is 100 parts by mass.

The content of the organic solvent is not particularly limited, but is preferably about 50 to 90% by mass relative to the total mass of the composition for forming a film, for example.

[Method for producing composition for film formation]

As a method for producing the composition for forming a film of the present invention, an organic solvent is added into an appropriate container, and while stirring with, for example, a high-speed stirrer, the polysiloxane-based compound, the radical photopolymerization initiator, and additives used as necessary are added and mixed. You can use this method.

Additionally, the method is not limited to this method, and the order of adding each material may be arbitrary. In addition, if the solid material is soluble in an organic solvent, it may be dissolved in advance before addition, and if it can be dispersed in the organic solvent directly or using a dispersant, etc., it may be dispersed in advance before addition.

[Physical properties of composition for film formation]

The composition for forming a film of the present invention has excellent tackiness.

The tackiness can be judged by the following test.

The non-volatile component of the composition for film formation was diluted with propylene glycol monomethyl acetate so that the concentration of the non-volatile component was 25% by mass, and a commercially available 50 mm horizontal coating was applied using a spin coater (MS-A100, manufactured by Mikasa) under coating conditions of 400 rpm and 60 seconds. A polysiloxane-based compound is coated on a vertical square soda glass substrate.

Next, a test piece for evaluation is produced by heating (prebake) at 80°C for 3 minutes.

The degree of traces left when touching the surface of the evaluation test piece coated with the composition for forming a film with a finger is visually confirmed, and if no finger traces remain, it can be judged that the tackiness is excellent.

The composition for forming a film of the present invention has excellent developability.

The developability can be judged by the following test.

The test piece for evaluation used to test the tackiness of the film-forming composition was exposed to a 2.38% by mass aqueous solution (developer) of tetramethylammonium hydroxide, the dissolution state was observed with the naked eye, and when complete dissolution was confirmed, the developability was excellent. It can be judged that it is.

The composition for forming a film of the present invention has excellent photocurability.

The photocurability can be judged by the following test.

100 parts by mass of the composition for forming a film was diluted with propylene glycol monomethyl acetate so that the concentration of the non-volatile component was 25%, and a commercially available 50 mm coating was used using a spin coater (MS-A100, manufactured by Mikasa) under the coating conditions of 400 rpm and 60 seconds. It is coated on a horizontal and vertical square soda glass substrate.

Next, after heating (prebake) at 80°C for 3 minutes, the test pattern was baked using a mask aligner (PLA-501FA, manufactured by Canon) under irradiation conditions of 100 mJ/cm2, and a portion was used as a developer. After being immersed in a 2.38% by mass aqueous solution (developer) of tetramethylammonium hydroxide for 1 minute, it is heated (post-baked) at 150°C for 30 minutes to produce a test piece for evaluation.

The film thickness (T1) of the exposed part of the part exposed to the developer and the film thickness (T2) of the unexposed part of the unexposed part were measured using a film thickness measuring device (Alpha-Step IQ surface profiler, manufactured by KLM-Tencor). When measured, if T1/T2 is 0.35 or more, photocurability can be judged to be excellent, and if T1/T2 is 0.55 or more, photocurability can be judged to be particularly excellent.

It is preferable that the composition for forming a film of the present invention has excellent corrosion evaluation.

The above corrosion evaluation can be judged by the following test.

When the evaluation test piece used to test the photocurability of the film-forming composition is exposed to a developer, the thinness of the line pattern portion of the exposed portion divided by the development time is evaluated as the dissolution rate (nm/s).

It is preferable that the dissolution rate is less than 1200 nm/s, and more preferably less than 600 nm/s.

<Method of forming hardened film>

The method for forming a cured film of the present invention includes a coating process of applying the film-forming composition of the present invention to a substrate, an exposure process of forming a cured film by irradiating active energy rays to the exposed area, and dissolving the coating solution in the unexposed area with a developer. It has a developing process to remove it.

The coating method in the coating process, the active energy ray and its irradiation method for irradiating the exposed area in the exposure process, and the developing solution for removing the coating solution from the exposed area are appropriately selected from those used in the conventional photolithography method. You can use it.

For example, the non-volatile component of the composition for forming a film is diluted to 25%, coated using a spin coater, heated (pre-baked) at 80°C for 3 minutes, and then mask-aligned. A cured film can be obtained by baking a test pattern under irradiation conditions of 100 mJ/cm2, immersing it in a developer for 1 minute, and then heating (post-baking) it at 150°C for 30 minutes.

Preferably, the prebake conditions are 80 to 100°C for 1 to 3 minutes.

The above irradiation conditions are preferably 20 to 120 mJ/cm2.

As for the post-bake conditions, it is preferable to process at 120 to 180°C for 30 to 60 minutes.

In addition, as the substrate, conventionally known glass substrates and plastic substrates used in touch panels can be appropriately used, and a substrate with a transparent electrode formed on the surface may be used.

In addition, when the surface has a transparent electrode, it is preferable to form a cured film of the film-forming composition of the present invention on the surface on which the transparent electrode is formed.

A laminate characterized by having a cured film of the composition for forming a film of the present invention on the above substrate is also an aspect of the present invention.

Additionally, a touch panel characterized by being formed using the laminate of the present invention is also an aspect of the present invention.

As the material constituting the touch panel, conventionally known materials can be appropriately used, except for using the laminate of the present invention.

[Example]

The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. In addition, unless otherwise specified, “%” means “% by mass” and “part” means “part by mass.”

The following were prepared as silane-based compounds (A) to (C) used in the synthesis of polysiloxane-based compounds.

<Silane compound (A)>

Tetraethoxysilane

<Silane compound (B)>

Phenyltrimethoxysilane

Methyltriethoxysilane

Dimethyldimethoxysilane

<Silane compound (C)>

3-(methacryloyloxy)propyltrimethoxysilane

(Examples 1 to 3, Comparative Examples 1 to 8)

(Synthesis of polysiloxane compounds)

In a reaction vessel equipped with a stirring device, reflux condenser, thermometer, and dropping funnel, add the silane compound (A), silane compound (B), and silane compound (C) at the mixing ratio shown in Table 1 so that the total mass is 100 g. I put it in. Next, it was dissolved in 400 g of isopropyl alcohol to obtain a uniform solution.

In addition, the number of water molecules is 4 times that of the total number of molecules of the silane-based compound (A), silane-based compound (B), and silane-based compound (C) into which water and nitric acid are added while stirring, and the number of molecules of nitric acid is 0.1. After adding the doubling amount and mixing for 3 hours while refluxing, the obtained reaction solution was cooled to room temperature.

Afterwards, 20.00 g of propylene glycol monomethyl ether acetate was added to the reaction solution, and methanol, water, and nitric acid, which were reaction by-products, were distilled off under reduced pressure to obtain a hydrolysis condensate solution.

Thereafter, propylene glycol monomethyl ether acetate was added to the hydrolysis condensate solution to obtain a hydrolysis condensate solution (siloxane compound solution) having a polysiloxane compound non-volatile component concentration of 45% by mass.

In addition, the weight average molecular weight (Mw) of the polysiloxane-based compounds was measured under the conditions described in this specification and was all in the range of 8,000 to 10,000.

In addition, the numerical value written in the row of each compound name in Table 1 means the number of moles, and the numerical value written in the row of [MC/(MA+MB)] means the composition ratio calculated by the above formula (1).

<Evaluation of polysiloxane compounds>

(Taekseong)

[Production of test pieces for evaluation]

The synthesized polysiloxane compounds were diluted with propylene glycol monomethyl acetate so that the concentration of non-volatile components was 25% by mass, and coated using a spin coater (MS-A100, manufactured by Mikasa) at 400 rpm and 60 seconds, commercially available. A polysiloxane-based compound was coated on a 50 mm horizontal cell square soda glass substrate.

Next, a test piece for evaluation was produced by heating (prebake) at 80°C for 3 minutes.

[Evaluation results]

The degree of traces remaining when touching the surface of the produced evaluation test piece coated with the polysiloxane-based compound with a finger was visually confirmed, and the tackiness of the polysiloxane-based compound was evaluated using the following evaluation criteria. The results are shown in Table 1.

○: No trace of finger remains

△: Some traces of fingers remain.

×: Finger marks clearly remain

(developability)

The test piece for evaluation produced during the evaluation of tackiness was exposed to a 2.38% by mass aqueous solution (developer) of tetramethylammonium hydroxide, the dissolution state was observed with the naked eye, and the developability of the polysiloxane-based compound was evaluated using the following evaluation criteria. The results are shown in Table 1.

○: Completely dissolved

△: Almost dissolved, but residue occurs

×: Insoluble

(Gwanggyeong Hwaseong Fortress)

[Production of test pieces for evaluation]

To 100 parts by mass of each polysiloxane compound synthesized, 2.5 parts by mass of Irgacure OXE02, 0.13 parts by mass of 4-methoxyphenol, and 0.6 parts by mass of BYK-310 were added, and then mixed with propylene so that the concentration of non-volatile components was 25%. It was diluted with glycol monomethyl acetate and coated on a commercially available 50 mm horizontal cell square soda glass substrate using a spin coater (MS-A100, manufactured by Mikasa) under coating conditions of 400 rpm and 60 seconds.

Next, after heating (prebake) at 80°C for 3 minutes, the test pattern was baked using a mask aligner (PLA-501FA, manufactured by Canon) under irradiation conditions of 100 mJ/cm2, and a portion was used as a developer. After being immersed in a 2.38% by mass aqueous solution (developer) of tetramethylammonium hydroxide for 1 minute, a test piece for evaluation was produced by heating (post-baking) at 150°C for 30 minutes.

[Evaluation results]

The film thickness (T1) of the exposed part of the part exposed to the developer and the film thickness (T2) of the unexposed part of the unexposed part were measured using a film thickness measuring device (Alpha-Step IQ surface profiler, manufactured by KLM-Tencor). And the photocurability of the polysiloxane-based compound was evaluated based on the following evaluation criteria. The results are shown in Table 1.

○: T1/T2 is 0.55 or more

△: T1/T2 is more than 0.35 and less than 0.55

×: T1/T2 is less than 0.35

<Production of composition for film formation>

The following materials were prepared to be used in producing the composition for forming a film.

<Polymerizable monomer>

Tris(2-hydroxyethyl)isocyanuric acid triacrylate (THITA, manufactured by Tokyo Kasei Industry Co., Ltd.)

Dipentaerythritol hexaacrylate (DPHA, manufactured by Tokyo Kasei Industry Co., Ltd.)

<Polymerization initiator>

O-acetyl-1-[6-(2-methylbenzoyl)-9-ethyl-9H-carbazol-3-yl]ethanone oxime (Irgacure OXE02, manufactured by BASF Japan)

<Other materials>

Carens MT PE-1 (thiol-based crosslinking agent, manufactured by Showa Denko)

4-methoxyphenol (polymerization inhibitor, 4-MeOPh, manufactured by Tokyo Kasei Industry Co., Ltd.)

BYK-310 (silicone-based surfactant, manufactured by Big Chemi Japan)

(Example 4)

In a container equipped with a high-speed stirring device, 100 parts by mass of the polysiloxane compound solution (non-volatile component concentration 45%) prepared in Example 1, 15 parts by mass of THITA, 5 parts by mass of DPHA, and Karenz MT PE-1 were placed in a container equipped with a high-speed stirring device. 5 parts by mass, 2.5 parts by mass of Irgacure OXE02, 0.13 parts by mass of 4-MeOPh, 0.6 parts by mass of BYK-310, and 135 parts by mass of propylene glycol monomethyl ether acetate (PGMEA) were added, stirred, and the film of Example 4 was obtained. A composition for forming was prepared.

(Examples 5 to 6, Comparative Examples 9 to 16)

A composition for forming a film was prepared in the same manner as in Example 4, except that the type of polysiloxane compound solution was changed as shown in Table 2.

In addition, although not described in Table 2, 135 parts by mass of propylene glycol monomethyl ether acetate (PGMEA) was used as in Example 1.

(Taekseong)

[Production of test pieces for evaluation]

Each film-forming composition produced was diluted with propylene glycol monomethyl acetate so that the concentration of the non-volatile component was 25% by mass, and applied using a spin coater (MS-A100, manufactured by Mikasa) at 400 rpm for 60 seconds. The film-forming composition was applied to a commercially available 50 mm square soda glass substrate.

Next, a heat (prebake) treatment at 80°C for 3 minutes was performed to produce a test piece for evaluation.

[Evaluation results]

The degree of traces left when touching the surface of the produced evaluation test piece coated with the film-forming composition with a finger was visually confirmed, and the tackiness of the film-forming composition was evaluated using the following evaluation criteria. The results are shown in Table 2.

○: No trace of finger remains

△: Some traces of fingers remain.

×: Finger marks clearly remain

(developability)

The test piece for evaluation produced during the evaluation of tackiness was exposed to a 2.38% by mass aqueous solution (developer) of tetramethylammonium hydroxide, the dissolution state was observed with the naked eye, and the developability of the polysiloxane-based compound was evaluated using the following evaluation criteria. The results are shown in Table 2.

○: Completely dissolved

△: Almost dissolved, but residue is generated

×: Insoluble

(Gwanggyeong Hwaseong Fortress)

[Production of test pieces for evaluation]

Each film-forming composition prepared was diluted with propylene glycol monomethyl acetate so that the concentration of non-volatile components was 25% by mass, and applied using a spin coater (MS-A100, manufactured by Mikasa) at 400 rpm for 60 seconds. The film-forming composition was applied to a commercially available 50 mm square soda glass substrate.

Next, after heating (prebake) at 80°C for 3 minutes, the test pattern was baked under irradiation conditions of 100mJ/cm2 using a mask aligner (PLA-501FA, manufactured by Canon), and a portion of it was used as a developer. After being immersed in a 2.38% by mass aqueous solution (developer) of tetramethylammonium hydroxide for 1 minute, it was heated (post-baked) at 150°C for 30 minutes to produce a test piece for evaluation.

[Evaluation results]

The film thickness (T1) of the exposed part of the part exposed to the developer and the film thickness of the unexposed part (T2) of the unexposed part were measured using a film thickness measuring device (Alpha-Step IQ surface profiler, manufactured by KLM-Tencor). The photocurability of the film forming composition was measured and evaluated based on the following evaluation criteria. The results are shown in Table 2.

○: T1/T2 is 0.55 or more

△: T1/T2 is more than 0.35 and less than 0.55

×: T1/T2 is less than 0.35

(corrosion)

The width of the line pattern portion of the exposed area when the test piece for evaluation produced during the above development evaluation was exposed to the developing solution was divided by the development time, and the value was taken as the dissolution rate (nm/s), and the following was used as the evaluation standard. The results are shown in Table 2.

○: Dissolution rate is less than 600 nm/s

△: Dissolution speed is more than 600nm/s and less than 1200nm/s

×: Dissolution speed is 1200 nm/s or more

It was confirmed that the polysiloxane-based compounds of Examples 1 to 3 were excellent in tackiness and developability, and were also excellent in photocurability. In addition, it was confirmed that the film-forming compositions of Examples 4 to 6 using the polysiloxane compounds of Examples 1 to 3 were excellent in tackiness, developability, photocurability and corrosion.

On the other hand, the polysiloxane-based compounds of Comparative Examples 1 to 6 and 8 whose composition ratio calculated by the above formula (1) was 0.1 or more had insufficient tackiness. In addition, the film-forming compositions of Comparative Examples 9 to 14 and 16 using the polysiloxane compounds of Comparative Examples 1 to 6 and 8 also had insufficient tackiness.

In addition, the polysiloxane-based compound of Comparative Example 7, whose composition ratio calculated by the above formula (1) was 0, had insufficient photocurability. In addition, the film-forming composition of Comparative Example 15 using the polysiloxane-based compound of Comparative Example 7 also had insufficient photocurability and corrosion.

The following matters are disclosed in this specification.

The present disclosure (1) includes a structural unit (A) derived from a silane-based compound (A) that is at least one selected from the group of tetraalkoxysilane and bis(trialkoxysilyl)alkane, an alkyltrialkoxysilane, and a dialkyldi It has a structural unit (B) derived from at least one silane compound (B) selected from the group of alkoxysilanes, cycloalkyltrialkoxysilanes, vinyltrialkoxysilanes, and phenyltrialkoxysilanes, and a radically polymerizable unsaturated double bond. It is a polysiloxane system compound containing at least a structural unit (C) derived from a silane-based compound (C) and having a structural ratio calculated by the following formula (1) greater than 0 and less than 0.1.

(In formula (1), MA represents the number of moles of the structural unit (A), MB represents the number of moles of the structural unit (B), and MC represents the number of moles of the structural unit (C).)

This disclosure (2) is the polysiloxane-based compound described in this disclosure (1), wherein the silane-based compound (A) is tetraethoxysilane.

This disclosure (3) is the polysiloxane-based compound described in this disclosure (1) or (2), wherein the silane compound (B) is phenyltrimethoxysilane and/or methyltriethoxysilane.

This disclosure (4) is a polysiloxane-based compound according to any one of the present disclosures (1) to (3), wherein the silane-based compound (C) is 3-(methacryloyloxy)propyltrimethoxysilane.

This disclosure (5) is a polysiloxane-based compound described in any one of this disclosure (1) to (4), wherein the composition ratio calculated by the above formula (1) is 0.03 or more and 0.08 or less.

This disclosure (6) is a composition for forming a film containing at least the polysiloxane-based compound described in any one of disclosures (1) to (5), a radical photopolymerization initiator, and an organic solvent.

This disclosure (7) is a composition for forming a film according to this disclosure (6), wherein the radical photopolymerization initiator contains a ketoxime ester group.

This disclosure (8) is a laminate formed by coating the composition for forming a film according to this disclosure (6) or (7).

This disclosure (9) is a touch panel using the laminate described in this disclosure (8).

This disclosure (10) includes a process of coating the film-forming composition according to this disclosure (6) or (7), an exposure process of forming a cured film by irradiating active energy rays to the exposed area, and applying a coating solution to the unexposed area. It is a method of forming a cured film, characterized by having a development process of removing by dissolving with a developing solution.

The polysiloxane-based compound of the present invention can be used to obtain a cured film with excellent tackiness, and also has excellent developability and photocurability, so it can be suitably used as a film applied to a light-transmitting substrate such as a touch panel.

Claims (10)

A structural unit (A) derived from at least one silane-based compound (A) selected from the group of tetraalkoxysilane and bis(trialkoxysilyl)alkane,
A structural unit (B) derived from at least one silane-based compound (B) selected from the group of alkyltrialkoxysilane, dialkyldialkoxysilane, cycloalkyltrialkoxysilane, vinyltrialkoxysilane, and phenyltrialkoxysilane,
Contains at least a structural unit (C) derived from a silane-based compound (C) having a radically polymerizable unsaturated double bond,
A polysiloxane-based compound whose composition ratio calculated by the following formula (1) is greater than 0 and less than 0.1.

(In formula (1), MA represents the number of moles of the structural unit (A), MB represents the number of moles of the structural unit (B), and MC represents the number of moles of the structural unit (C).) The polysiloxane-based compound according to claim 1, wherein the silane-based compound (A) is tetraethoxysilane. The polysiloxane-based compound according to claim 1 or 2, wherein the silane-based compound (B) is phenyltrimethoxysilane and/or methyltriethoxysilane. The polysiloxane-based compound according to claim 1 or 2, wherein the silane-based compound (C) is 3-(methacryloyloxy)propyltrimethoxysilane. The polysiloxane-based compound according to claim 1 or 2, wherein the composition ratio calculated by the formula (1) is 0.03 or more and 0.08 or less. A composition for forming a film containing at least the polysiloxane-based compound according to claim 1 or 2, a radical photopolymerization initiator, and an organic solvent. The composition for forming a film according to claim 6, wherein the radical photopolymerization initiator contains a ketoxime ester group. A laminate formed by coating the composition for forming a film according to claim 6. A touch panel made using the laminate according to claim 8. Curing characterized by comprising a process of applying the composition for forming a film according to claim 6, an exposure process of forming a cured film by irradiating active energy rays to the exposed area, and a development process of dissolving and removing the coating solution in the unexposed area with a developing solution. Method of forming the film.