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  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
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  • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
  • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
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  • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
  • C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
  • C08F299/08—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polysiloxanes
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  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/04—Polysiloxanes
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  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
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  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
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  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
  • C08L83/04—Polysiloxanes
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  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
  • C08L83/04—Polysiloxanes
  • C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
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  • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
  • C09D183/04—Polysiloxanes
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  • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
  • C09D183/04—Polysiloxanes
  • C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
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  • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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  • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
  • C09D7/40—Additives
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  • C08G2150/00—Compositions for coatings
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  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/04—Polysiloxanes
  • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/04—Polysiloxanes
  • C08G77/38—Polysiloxanes modified by chemical after-treatment

Definitions

• the present invention relates to an alkali-soluble, ultraviolet-curable organopolysiloxane curable by actinic rays, such as ultraviolet rays or electron beams, and an ultraviolet-curable composition containing the same.
• the curable polysiloxane of the present invention has high solubility in alkaline aqueous solutions and good ultraviolet curing properties, so it exhibits excellent lithography performance and is used as an insulating material for electronic and electrical devices that require patterning, especially coatings. It is suitable as a material for use as an agent.
• silicone resins Due to its high heat resistance and excellent chemical stability, silicone resins have been used as coating agents, potting agents, insulating materials, etc. for electronic and electrical devices. Among silicone resins, UV-curable silicone compositions have also been reported so far.
• Touch panels are used in various display devices such as mobile devices, industrial equipment, and car navigation systems. In order to improve the detection sensitivity, it is necessary to suppress the electrical influence from the light emitting parts such as light emitting diodes (LED) and organic EL devices (OLED). placed. On the other hand, a thin display device such as an OLED has a structure in which many functional thin layers are laminated. In recent years, studies have been made to improve the visibility of a display device by laminating insulating layers formed from an acrylate-based polymer with a high refractive index and a polyfunctional polymerizable monomer above and below a touch screen layer. (For example, Patent Documents 1 and 2)
• Patent Document 3 discloses a lithographically curable composition
• a lithographically curable composition comprising a silsesquioxane having a carboxyl group and a methacryloxy group, a polyfunctional polymerizable monomer, an inorganic filler, a polymerization initiator, and an organic solvent.
• This composition contains a polyfunctional polymerizable monomer at a concentration of 33% or more of the total curable components in order to improve the sensitivity during curing and the adhesion of the cured product.
• Patent Document 4 discloses a silsesquioxane having a group selected from a carboxy group, a carboxylic acid anhydride group, a phenolic hydroxyl group and a polymerizable double bond, a photopolymerization initiator, and a lithography method comprising an organic solvent.
• Possible curable compositions are disclosed. However, in the present composition, there is still room for improvement in terms of mechanical strength (especially brittleness) and transparency of coatings with large thicknesses, and substantially, at a concentration of 64% or more of the total curable component A composition comprising a non-silicon-containing polyfunctional polymerizable monomer.
• an ultraviolet-curable composition containing an organopolysiloxane having an ultraviolet-curable group and a hydrophilic group has been disclosed, the organopolysiloxane itself has high solubility in an alkaline aqueous solution, and a polyfunctional polymerizable monomer is used.
• a polyfunctional polymerizable monomer is used.
• the present invention has been made to solve the above problems, and has one or more monovalent functional groups having both a hydrophilic group and an ultraviolet curable group in one molecule on a silicon atom, and , an ultraviolet-curable organopolysiloxane having solubility in an alkaline aqueous solution as a whole organopolysiloxane; It was completed by discovering that the cured product (cured film) has sufficient mechanical strength and good transparency without using it.
• the present invention relates to an ultraviolet-curable organopolysiloxane and an ultraviolet-curable composition containing the same.
• the composition is cured by forming bonds with ultraviolet-curable functional groups, and the curing method is UV irradiation. Any method that allows the UV-curable functional group to undergo a curing reaction can be used, for example electron beam irradiation may be used to cure the composition of the present invention.
• the UV-curable organopolysiloxane of the present invention has at least one monovalent functional group in one molecule that is bonded to a silicon atom and has both a hydrophilic group and an UV-curable group, and has an organopolysiloxane
• the siloxane as a whole is characterized by having solubility in an alkaline aqueous solution.
• the ultraviolet curable organopolysiloxane may have one or more siloxane units selected from repeating units (1) and (2) below in one molecule.
• R 1 RSiO 2/2 (1)
• R 1 is a monovalent functional group having both a hydrophilic group and a UV-curable group, and R is an unsubstituted or fluorine-substituted monovalent hydrocarbon group, an alkoxy group, and a hydroxyl group. is a group of choice, A is R 1 or R, and A includes at least one R 1 )
• the ultraviolet curable organopolysiloxane may have one or more siloxane units (1) per molecule (that is, it is essential).
• the UV-curable organopolysiloxane may further contain the following siloxane unit (3).
• (R 2 RSiO 2/2 ) (3) (Wherein, R 2 is a monovalent group having an ultraviolet curable group and no hydrophilic group, and R is the above group)
• the hydrophilic group in the monovalent functional group in the ultraviolet-curable organopolysiloxane is preferably a group selected from carboxyl groups, hydroxyl groups, phenolic hydroxyl groups, and polyether groups.
• the UV-curable group in the monovalent functional group in the UV-curable organopolysiloxane is preferably a group selected from an epoxy group, an oxetane group, a vinyl ether group, and a (meth)acryloxy group.
• the UV-curable organopolysiloxane has the average unit formula: (B 3 SiO 1/2 ) a (R 1 RSiO 2/2 ) b1 (R 2 RSiO 2/2 ) b2 (RSiO 3/2 ) c (SiO 4/2 ) d (4) (Wherein, R 1 , R 2 and R are each independently the same groups as above, each B is independently a group selected from R 1 , R 2 and R; a is 0 or a positive number, b1 is a number within the range of 1 to 100, b2 is a number within the range of 0 to 50, and (c + d) is a positive number)
• a branched organopolysiloxane represented by is preferred.
• the value of (b1+b2)/(a+b1+b2+c+d) in the average unit formula (4) of the ultraviolet-curable organopolysiloxane is preferably 0.1 or more and 0.5 or less.
• the UV-curable organopolysiloxane preferably contains one or more of the following siloxane units (5) in the molecule. (RSiO3 /2 ) (5) (Wherein, R is the same group as described above)
• the hydrophilic group in the monovalent functional group in the UV-curable organopolysiloxane is preferably a carboxyl group, and the UV-curable group is preferably a (meth)acryloxy group.
• the solubility of the UV-curable organopolysiloxane in an alkaline aqueous solution was evaluated by applying the organopolysiloxane to a glass plate so that the thickness after application was 4 ⁇ m, and then coating the coating film with tetramethylammonium hydroxide (TMAH).
• TMAH tetramethylammonium hydroxide
• the mass reduction rate of the coating film comprising the organopolysiloxane is preferably 90% by mass or more, 95% by mass or more, or 98% by mass or more.
• the present invention further provides an ultraviolet curable composition containing at least the following components.
• A the UV-curable organopolysiloxane described above;
• B Photopolymerization initiator
• A Amount of 0.5 to 10 parts by mass per 100 parts by mass of component
• C Organic solvent
• the present invention further provides a cured product of the above UV-curable composition. Also provided is a method of using the cured product as an insulating coating layer.
• the present invention further provides a display device, such as a liquid crystal display, an organic EL display, and an organic EL flexible display, including a layer comprising a cured product of the ultraviolet curable composition.
• a display device such as a liquid crystal display, an organic EL display, and an organic EL flexible display, including a layer comprising a cured product of the ultraviolet curable composition.
• the UV-curable organopolysiloxane of the present invention has good coatability on substrates, and is highly soluble in alkaline aqueous solutions that are commonly used in the development process for forming patterns of desired shapes.
• unreacted/uncured organopolysiloxane and the curable composition containing the same can be easily removed by washing with an alkaline aqueous solution. High-precision patterning is possible in the process.
• the cured product formed from the UV-curable composition containing the UV-curable organopolysiloxane of the present invention is optically transparent, can be designed with a wide range of hardness, etc., and has a low dielectric constant. There are advantages.
• the curable composition according to the present invention can be used as a material for forming a low dielectric constant layer, particularly a low dielectric constant material for electronic devices, particularly an insulating layer, in any field where a material having a low dielectric constant is required. materials, particularly patterning materials and coating materials.
• the UV-curable organopolysiloxane of the present invention has at least one monovalent functional group in one molecule that is bonded to a silicon atom and has both a hydrophilic group and an UV-curable group, and has an organopolysiloxane
• the siloxane as a whole is soluble in an alkaline aqueous solution (in the present invention, it may be expressed as "alkali-soluble").
• the ultraviolet-curable composition of the present invention contains (A) the organopolysiloxane, (B) a photopolymerization initiator, and (C) an organic solvent as essential components.
• alkali-soluble means that the formed coating film is soluble in an aqueous alkaline solution that is commonly used in the development process performed to form a pattern of a desired shape.
• Basic aqueous solutions of sodium hydroxide, potassium hydroxide, quaternary ammonium salts and the like are well known as alkaline aqueous solutions, but an aqueous solution of tetramethylammonium hydroxide is typically used, and in the present invention, this solution is used. It means that it is soluble in alkaline aqueous solution.
• the expression "soluble in an alkaline aqueous solution” means that the organopolysiloxane of the present invention is applied to a glass plate to a thickness of 4 ⁇ m, and then the coating film is treated with tetramethylammonium hydroxide (TMAH ) in a 2.38% aqueous solution of ) for 1 minute and then washed with water, the weight reduction rate of the coating film composed of the organopolysiloxane is 90% by mass or more, and in particular, it was evaluated by the above method.
• TMAH tetramethylammonium hydroxide
• a common method for applying organopolysiloxane onto a glass plate is spin coating or the like, and in the case of applying using an organic solvent, which will be described later, the organic solvent must be removed in advance by drying or the like.
• the above method can be used to evaluate the solubility of the UV-curable composition containing the organopolysiloxane according to the present invention in alkaline aqueous solution.
• the organopolysiloxane containing one or more siloxane units selected from the repeating units (1) and (2) described above is more soluble in alkaline aqueous solutions than the organopolysiloxane containing only silsesquioxane units.
• the solubility of a coating film made of the organopolysiloxane in alkaline aqueous solution is evaluated by the method described above, the weight reduction rate of the coating film is 98 mass. % or more, there is a tendency to obtain an organopolysiloxane having particularly excellent alkali solubility.
• the UV-curable organopolysiloxane of the present invention has, in one molecule, one or more monovalent functional groups bonded to silicon atoms and having both a hydrophilic group and an UV-curable group, and is an organopolysiloxane having an alkali solubility of
• the molecular structure is not limited as long as it can achieve this purpose, and may be linear, branched, cyclic, cage-like, or any other structure.
• the UV-curable organopolysiloxane of the present invention preferably has one or more siloxane units selected from repeating units (1) and (2) below in one molecule. . (R 1 RSiO 2/2 ) (1) ( A3SiO1 / 2) (2) (Wherein R 1 is a monovalent functional group having both a hydrophilic group and a UV-curable group, and R is an unsubstituted or fluorine-substituted monovalent hydrocarbon group, an alkoxy group, and a hydroxyl group. selected groups, A is R 1 or R, and A includes at least one R 1 )
• the organopolysiloxane preferably contains the siloxane unit (1).
• the toughness of a coating having a particularly large film thickness is high, and the transparency is also good, as compared with a cured product consisting only of a silsesquioxane unit.
• the organopolysiloxane can further contain the following siloxane unit (3).
• R 2 is a monovalent functional group having an ultraviolet-curing group and no hydrophilic group, and R is the group described above. (R 2 RSiO 2/2 ) (3)
• the UV-curable organopolysiloxane of the present invention has a monovalent functional group bonded to silicon atoms and having both a hydrophilic group and an UV-curable group, and the hydrophilic group in the monovalent functional group
• a group selected from a carboxyl group, a hydroxyl group, a phenolic hydroxyl group, and a polyether group can preferably be used as the functional group.
• a carboxyl group is most preferable because it has a large effect of increasing the alkali solubility.
• a group selected from an epoxy group, an oxetane group, a vinyl ether group, and a (meth)acryloxy group can be preferably used as the UV-curable group in the monovalent functional group.
• an epoxy group and a (meth)acryloxy group are more preferable, and a (meth)acryloxy group is most preferable, from the viewpoint of ease of production and raw material availability.
• the organopolysiloxane has the average unit formula (4): (B 3 SiO 1/2 ) a (R 1 RSiO 2/2 ) b1 (R 2 RSiO 2/2 ) b2 (RSiO 3/2 ) c (SiO 4/2 ) d (4) It is a branched organopolysiloxane represented by (Wherein, R 1 , R 2 and R are each independently the same groups as described above, B is each independently a group selected from R, R 1 and R 2 , a is 0 or is a positive number, b1 is a number in the range 1-100, b2 is a number in the range 0-50, and (c+d) is a positive number)
• the ratio of each structural unit is not limited, but the lower limit of the value of (b1+b2)/(a+b1+b2+c+d) is preferably 0.1 or more, and 0 0.15 or higher is more preferred. On the other hand, a preferable upper limit of the value is 0.5, and a value of 0.4 or less is more preferable.
• the branched organopolysiloxane may further have siloxane units selected from T units represented by (RSiO 3/2 ) and Q units represented by (SiO 4/2 ), in particular (RSiO 3 /2 ) may have a siloxane T unit.
• UV-curable organopolysiloxane preferably used in the present invention include polysiloxanes composed of combinations of the following siloxy units.
• M is a trimethylsiloxy unit
• M Vi is a dimethylvinylsiloxy unit
• M R1 is a siloxane unit having a monovalent group and two methyl groups having both a hydrophilic group and a UV-curable group
• D is a dimethylsiloxy unit
• D R1 is a siloxane unit having a monovalent group and a methyl group having both a hydrophilic group and an ultraviolet curable group
• D R2 is a monovalent group having an ultraviolet curable group
• T is a methylsiloxy unit
• TR is an alkylsiloxy or alkenylsiloxy unit (the alkyl group is an alkyl group that may be partially fluorine-substituted, vinyl, propyl, hex
• Examples of preferred combinations of siloxy units constituting UV-curable organopolysiloxane M R1 T Ph , MM R1 T Ph , M Vi M R1 T Ph , M R1 DT Ph , MM R1 DT Ph , M Vi M R1 DT Ph , M R1 Q, MM R1 Q , M Vi M R1 Q, M R1 DQ, MM R1 DQ, M Vi M R1 DQ, M R1 T, MM R1 T, M Vi M R1 T, M R1 TTR , MM R1 TTR , M Vi M R1 TTR , M R1 DT , MM R1 DT , M Vi M R1 DT, M R1 DTT R , MM R1 DTT R , M Vi M R1 DTT R , MD R1 T, MD R1 D R2 T, D R1 T, D R1 T R , D R1D R2 TR , MD R1 TTR
• the substituent R in the branched organopolysiloxane is a group selected from unsubstituted or fluorine-substituted monovalent hydrocarbon groups, alkoxy groups, and hydroxyl groups.
• An unsubstituted or fluorine-substituted monovalent hydrocarbon group is preferably a group selected from unsubstituted or fluorine-substituted alkyl, cycloalkyl, arylalkyl, and aryl groups having 1 to 20 carbon atoms. is.
• alkyl group examples include groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, pentyl, hexyl and octyl, with methyl and hexyl being particularly preferred.
• cycloalkyl group examples include cyclopentyl and cyclohexyl.
• arylalkyl group examples include benzyl and phenylethyl groups. Examples of the aryl group include a phenyl group and a naphthyl group.
• fluorine-substituted monovalent hydrocarbon groups examples include 3,3,3-trifluoropropyl and 3,3,4,4,5,5,6,6,6-nonafluorohexyl groups. but the 3,3,3-trifluoropropyl group is preferred.
• Alkoxy groups include methoxy, ethoxy, propoxy and isopropoxy groups.
• the refractive index of the branched organopolysiloxane can be designed within a desired range (for example, 1.40 to 1.60) depending on the type of substituent R in the branched organopolysiloxane.
• the branched organopolysiloxane has a refractive index of 1.5. It can be lowered to 50 or less and 1.45 or less, and can be used as a raw material for a curable composition having a lower refractive index.
• the substituent R 1 described in formula (1) and the like is a monovalent functional group bonded to the silicon atom and having both a hydrophilic group and an ultraviolet-curing group.
• the linking group R4 is a chain divalent hydrocarbon group having 2 to 10 carbon atoms, and includes ethylene, propylene, butylene, hexylene and the like, with ethylene and propylene being preferred.
• the linking group X is an oxygen atom, a sulfur atom, or an NR7 group, preferably an oxygen atom.
• R7 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 3 carbon atoms.
• the linking group R5 is a trivalent hydrocarbon group having 3 to 10 carbon atoms, chain, cyclic, or a combination thereof, that is, an alkanetriyl group.
• An yl group can be used as a preferred linking group. (7) (Wherein, * represents a binding site)
• Y is a group containing a monovalent UV-curable group.
• Usable UV-curable groups include an epoxy group, an oxetane group, a vinyl ether group, a (meth)acryloxy group, etc., and a (meth)acryloxy group is a preferred UV-curable group.
• Preferred examples of Y are acryloxy and methacryloxy groups.
• Z is a hydrophilic group, preferably a hydroxyl group, a hydroxyl group-containing group, or a carboxyl group-containing group.
• a hydroxyl group-containing group an alcoholic hydroxyl group or a phenolic hydroxyl group bonded via a divalent linking group is used may Moreover, it may and preferably has a carboxyl group represented by —CO 2 H bonded via a divalent linking group.
• the linking group R 6 is a divalent hydrocarbon group which may optionally contain an oxygen atom or a sulfur atom as a heteroatom, specifically a linear, branched or cyclic divalent group having 2 to 12 carbon atoms. Hydrocarbon group; sulfur-containing straight-chain, branched, or cyclic divalent hydrocarbon group; oxygen-containing straight-chain, branched, or cyclic divalent hydrocarbon group. More specific examples include divalent groups exemplified by the following structural formula (8). Among them, 6a, 6b, 6c, 6d, 6e, 6i, 6k, 6m, 6p, 6q, 6q and 6s can be preferably used. (8) (Wherein, * represents a binding site)
• Substituent R2 is a monovalent group having a UV-curable group and no hydrophilic group.
• a group selected from an epoxy group, an oxetane group, a vinyl ether group, and a (meth)acryloxy group can be preferably used, and as described above, an epoxy group and a (meth)acryloxy group are more preferable.
• R 2 examples include glycidoxyethyl, glycidoxypropyl, 2-(3,4-epoxycyclohexyl)ethyl, 3-(3,4-epoxycyclohexyl)propyl, acryloxy A propyl group, a methacryloxypropyl group, an acryloxyoctyl group, and a methacryloxyoctyl group can be mentioned.
• the UV-curable organopolysiloxane of the present invention is preferably a branched organopolysiloxane having monovalent functional groups having both (meth)acryloxy groups and carboxyl groups bonded to silicon atoms.
• each molecule preferably has an average of 2.5 or more monovalent functional groups.
• the UV-curable organopolysiloxane may contain a monovalent group (substituent R 2 ) having an UV-curable group and no hydrophilic group. Therefore, the number of UV-curable groups and the number of hydrophilic groups in the molecule may be different.
• the average number of UV-curable groups in the molecule is preferably 2 or more, more preferably 3 or more, and more preferably 5 or more.
• the average number of hydrophilic groups in the molecule is preferably 2 or more, more preferably 3 or more.
• the molecular weight of the UV-curable organopolysiloxane of the present invention is not particularly limited.
• the average molecular weight is preferably from 1,000 to 100,000, more preferably from 1,000 to 50,000, and even more preferably from 2,000 to 30,000.
• the method for producing the ultraviolet-curable organopolysiloxane of the present invention is also not particularly limited.
• 1) UV-curable organopolysiloxane is produced and a functional group having a hydrophilic group is imparted, and 2) reactive organopolysiloxane having no hydrophilic group and UV-curable group is prepared.
• methods 1) and 2) are preferably applicable.
• a specific example is a method of producing an epoxy group-containing UV-curable organopolysiloxane, converting the functional groups of the epoxy groups in stages, and imparting functional groups having a (meth)acryloxy group and a carboxyl group.
• the ultraviolet curable composition of the present invention contains the following three components.
• Component (A) is the main component of the detailed invention.
• Component (B) is a component that catalyzes the curing reaction of component (A) by ultraviolet rays, and compounds known as photopolymerization initiators are usually applicable.
• a photocationic polymerization initiator is used as the photopolymerization initiator.
• photocationic polymerization initiators compounds capable of generating Bronsted acids or Lewis acids by irradiation with ultraviolet rays or electron beams, so-called photoacid generators, are known. Acids are known to cause reactions between cationically polymerizable functional groups.
• a radical photopolymerization initiator can be used as the photopolymerization initiator.
• the photo-radical polymerization initiator can cure the composition of the present invention by generating free radicals upon irradiation with ultraviolet rays, which induce radical polymerization reactions.
• photocationic polymerization initiator used in the ultraviolet-curable composition of the present invention can be arbitrarily selected from those known in the art and is not particularly limited. Strong acid-generating compounds such as diazonium salts, sulfonium salts, iodonium salts, and phosphonium salts are known as photocationic polymerization initiators, and these can be used.
• photocationic polymerization initiators include bis(4-tert-butylphenyl)iodonium hexafluorophosphate, cyclopropyldiphenylsulfonium tetrafluoroborate, dimethylphenacylsulfonium tetrafluoroborate, diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroarce diphenyliodonium tetrafluoromethanesulfonate, 2-(3,4-dimethoxystyryl)-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-[2-(furan-2-yl) Vinyl]-4,6-bis(trichloromethyl)-1,3,5-triazine, 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate, 2-[2-(5-methyl)
• the amount of the photocationic polymerization initiator to be added to the UV-curable composition of the present invention is not particularly limited as long as the desired photo-curing reaction occurs.
• a photocationic polymerization initiator can be used in an amount of 0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, particularly 0.5 to 5 parts by weight, based on 100 parts by weight of the alkali-soluble organopolysiloxane. preferable.
• a photosensitizer can also be used in combination with the photocationic polymerization initiator.
• the use of a sensitizer can increase the photon efficiency of the polymerization reaction, making longer wavelength light available for the polymerization reaction than when only the photoinitiator is used. is known to be particularly effective when the coating thickness of is relatively thick or when relatively long wavelength LED light sources are used.
• Sensitizers include anthracene compounds, phenothiazine compounds, perylene compounds, cyanine compounds, merocyanine compounds, coumarin compounds, benzylidene ketone compounds, (thio)xanthene or (thio)xanthone compounds such as isopropyl Thioxanthone, 2,4-diethylthioxanthone, alkyl-substituted anthracenes, squarium-based compounds, (thia)pyrylium-based compounds, porphyrin-based compounds, etc. are known, and any photosensitizer may be used in the curing of the present invention without being limited to these. can be used in sexual compositions.
• Radical photopolymerization initiators are roughly classified into photocleavage type and hydrogen abstraction type, but the photoradical polymerization initiator used in the composition of the present invention is arbitrarily selected from those known in the art. It can be selected and used, and is not particularly limited to a specific one.
• photoradical polymerization initiators include acetophenone, p-anisyl, benzyl, benzoin, benzophenone, 2-benzoylbenzoic acid, 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(dimethylamino)benzophenone.
• benzoin methyl ether benzoin isopropyl ether, benzoin isobutyl ether, benzoin ethyl ether, 4-benzoylbenzoic acid, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl-1, 2'-biimidazole, methyl 2-benzoylbenzoate, 2-(1,3-benzodioxol-5-yl)-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-benzyl -2-(dimethylamino)-4'-morpholinobtyrophenone, ( ⁇ )-camphorquinone, 2-chlorothioxanthone, 4,4'-dichlorobenzophenone, 2,2-diethoxyacetophenone, 2,2-dimethoxy-2- Phenylacetophenone, 2,4-diethylthioxanthene-9-one, diphenyl(
• Omnirad registered trademark
• 651, 184, 1173, 2959, 127, 907, 369, 369E, and 379EG alkylphenone-based photopolymerization initiators, manufactured by IGM Resins BV
• IGM Resins BV radical photopolymerization initiators
• Omnirad registered trademark
• TPO H acylphosphine oxide photoinitiators
• IGM RESINS BV Omnirad (registered trademark) MBF and 754 (intramolecular hydrogen abstraction type photoinitiator IGM Resins BV), Irgacure® OXE01 and OXE02 (oxime ester-based non-social polymerization initiators, BASF).
• the amount of the radical photopolymerization initiator to be added to the curable composition of the present invention is not particularly limited as long as the desired photopolymerization reaction or photocuring reaction occurs, but generally the component (A) of the present invention It is used in an amount of 0.1 to 10 parts by weight, preferably 0.5 to 5 parts by weight, per 100 parts by weight of the UV-curable alkali-soluble organopolysiloxane.
• a photosensitizer can also be used in combination with the photoradical polymerization initiator.
• the use of a sensitizer can be expected to have the effect of increasing the photon efficiency of the polymerization reaction, as in the case of using the photocationic polymerization initiator.
• the photosensitizer the above-described photosensitizers that can be used in combination with the photocationic polymerization initiator are exemplified and can be preferably used.
• the UV-curable composition of the present invention preferably contains (C) an organic solvent for the purpose of adjusting the coatability of the UV-curable organopolysiloxane, adjusting the film thickness of the coating film, and improving the dispersibility of the photopolymerization initiator.
• organic solvents conventionally blended in various UV-curable compositions can be used without particular limitation.
• organic solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n.
• ketones lactic acid alkyl esters such as methyl 2-hydroxypropionate and ethyl 2-hydroxypropionate; ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, 3 -methyl ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate, ethyl hydroxyacetate, methyl 2-hydroxy-3-methylbutanoate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, 3-methyl -3-methoxybutyl propionate, ethyl acetate, n-propyl acetate, i-propyl acetate, n-butyl acetate, i-butyl acetate, n-pentyl formate, i-pentyl acetate, n-butyl propionate, ethyl buty
• the content of the organic solvent is not particularly limited, and is appropriately set according to (A) the miscibility with the UV-curable organopolysiloxane, the thickness of the coating film formed from the UV-curable composition, and the like. Typically, it is used in an amount of 50 to 10,000 parts by weight per 100 parts by weight of component (A). That is, the solute concentration of the UV-curable organopolysiloxane is preferably 1 to 50% by mass, more preferably 2 to 40% by mass.
• the cured product obtained from the UV-curable composition of the present invention depends on the molecular structure of component (A) and the number of hydrophilic groups and UV-curable groups per molecule. Depending on the amount added, the desired physical properties of the cured product and the curing speed of the curable composition can be obtained, and further according to the amount of component (C), the viscosity of the curable composition will be the desired value. can be designed to A cured product obtained by curing the ultraviolet curable composition of the present invention is also included in the scope of the present invention.
• the shape of the cured product obtained from the curable composition of the present invention is not particularly limited, and may be a thin coating layer, a molded product such as a sheet, or a laminate or a display device. It may be used as a sealing material or an intermediate layer.
• the cured product obtained from the composition of the present invention is preferably in the form of a thin-film coating layer, particularly preferably a thin-film insulating coating layer.
• the UV-curable composition of the present invention is suitable for use as a coating agent, particularly an insulating coating agent for electronic and electrical devices.
• additives In addition to the above ingredients, further additives may be added to the compositions of the present invention as desired. Examples of additives include, but are not limited to, the following.
• An adhesion promoter can be added to the ultraviolet curable composition of the present invention in order to improve adhesion and adhesion to substrates in contact with the composition.
• an adhesion-imparting agent may be added to the curable composition of the present invention. is preferred. Any known adhesion promoter can be used as the adhesion promoter as long as it does not inhibit the curing reaction of the composition of the present invention.
• adhesion promoters examples include trialkoxysiloxy groups (e.g., trimethoxysiloxy group, triethoxysiloxy group) or trialkoxysilylalkyl groups (e.g., trimethoxysilylethyl group, triethoxysilylethyl group) and a hydrosilyl group or an alkenyl group (e.g., vinyl group, allyl group), or an organosiloxane oligomer having a linear, branched or cyclic structure with about 4 to 20 silicon atoms; trialkoxy Organosilanes having a siloxy group or a trialkoxysilylalkyl group and a methacryloxyalkyl group (e.g., 3-methacryloxypropyl group), or organosilanes having a linear, branched or cyclic structure having about 4 to 20 silicon atoms Siloxane oligomer; trialkoxysiloxy group
• the amount of the adhesion promoter added to the ultraviolet curable composition of the present invention is not particularly limited, but since it does not promote the curing properties of the curable composition and the discoloration of the cured product, , 0.01 to 5 parts by mass, or preferably 0.01 to 2 parts by mass.
• additives may be added to the ultraviolet curable composition of the present invention in addition to or instead of the adhesion imparting agent described above.
• Additives that can be used include leveling agents, silane coupling agents that are not included in the adhesiveness imparting agents described above, ultraviolet absorbers, antioxidants, polymerization inhibitors, fillers (reinforcing fillers, insulating and functional fillers such as thermally conductive fillers).
• Suitable additives can be added to the composition of the present invention, if desired.
• a thixotropic agent may be added to the composition of the present invention as necessary, particularly when used as a sealing material.
• the method for producing the cured film is not particularly limited as long as it is a method capable of curing the film made of the ultraviolet-curable composition described above.
• a known lithographic process can be applied, preferably to produce a patterned cured film.
• the substrate is not particularly limited, and various substrates such as a glass substrate, a silicon substrate, and a glass substrate coated with a transparent conductive film can be used.
• a known method using a coating device such as a spin coater, a roll coater, a bar coater, a slit coater, or the like can be applied to apply the ultraviolet curable composition onto the substrate.
• the applied curable composition is optionally heated and dried to remove the solvent.
• a method of drying on a hot plate at a temperature of 80 to 120° C., preferably 90 to 100° C. for 1 to 2 minutes, a method of standing at room temperature for several hours, and a hot air heater or infrared heater.
• Examples include a method of heating for several tens of minutes to several hours.
• Position-selective exposure of the coating film is usually performed through a photomask or the like, using a known active energy ray light source including ultraviolet light sources such as high-pressure mercury lamps, metal halide lamps and LED lamps, and laser light sources such as excimer laser light. done.
• a negative photomask or a positive photomask can be used.
• the energy dose to be irradiated depends on the structure of the curable composition, but is typically about 100 to 1,000 mJ/cm2.
• a developer In order to form a pattern of the desired shape, it is developed with a developer.
• Alkaline aqueous solutions and organic solvents are known as developing solutions, but development with alkaline aqueous solutions is the mainstream.
• Both an aqueous solution of an inorganic base and an aqueous solution of an organic base can be used as the alkaline aqueous solution.
• Suitable developers include basic aqueous solutions of sodium hydroxide, potassium hydroxide, sodium carbonate, ammonia, quaternary ammonium salts and the like, with aqueous solutions of tetramethylammonium hydroxide being particularly preferred.
• a developing method is not particularly limited, and for example, a dipping method, a spray method, or the like can be applied.
• the UV-curable organopolysiloxane and the UV-curable composition containing it as a main component according to the present invention have excellent UV-curing properties, and at the same time, are remarkably excellent in alkali solubility.
• the development step it has the advantage that simple and highly accurate pattern formation can be performed, and the mechanical strength and transparency of the resulting cured film are excellent.
• Post-heating is generally preferred for the patterned cured film after development.
• the PEB temperature is not particularly limited as long as the patterned cured film is not thermally decomposed or deformed, but is preferably 150 to 250.degree.
• the UV-curable composition of the present invention is particularly useful as a material for forming insulating layers that constitute various articles, particularly electronic devices and electrical devices.
• the composition can be designed to have a low dielectric constant of less than 3.0 after curing.
• the curable composition of the present invention is particularly suitable as a material for forming an insulating layer of display devices such as touch panels and displays because the cured product obtained therefrom has good transparency.
• the insulating layer may form any desired pattern, as described above, if desired. Therefore, a display device such as a touch panel and a display including an insulating layer obtained by curing the ultraviolet curable composition of the present invention is also one aspect of the present invention.
• the curable composition of the present invention can be used to coat an article and then cured to form an insulating coating layer (insulating film). Therefore, the composition of the present invention can be used as an insulating coating agent. A cured product formed by curing the curable composition of the present invention can also be used as an insulating coating layer.
• the insulating film formed from the curable composition of the present invention can be used for various purposes other than the display device. In particular, it can be used as a component of electronic devices or as a material used in the process of manufacturing electronic devices. Electronic devices include electronic equipment such as semiconductor devices and magnetic recording heads.
• the curable composition of the present invention can be used for semiconductor devices such as LSI, system LSI, DRAM, SDRAM, RDRAM, D-RDRAM, insulating films for multi-chip module multilayer wiring boards, interlayer insulating films for semiconductors, and etching stopper films. , a surface protective film, a buffer coat film, a passivation film in LSI, a cover coat for flexible copper-clad plates, a solder resist film, and a surface protective film for optical devices.
• Refractive index of UV curable organopolysiloxane A digital refractometer (RX-7000 ⁇ manufactured by Atago Co., Ltd.) was used to measure the refractive index (n D ) of the synthesized organopolysiloxane in propylene glycol methyl ether acetate (PGMEA) solution at 25°C. Solutions with various polymer concentrations were prepared and measured, and the nD of the synthesized organopolysiloxane was calculated by extrapolation.
• RX-7000 ⁇ manufactured by Atago Co., Ltd. was used to measure the refractive index (n D ) of the synthesized organopolysiloxane in propylene glycol methyl ether acetate (PGMEA) solution at 25°C. Solutions with various polymer concentrations were prepared and measured, and the nD of the synthesized organopolysiloxane was calculated by extrapolation.
• TMAH dissolution test B Only the edge portion of the cured coating film (less than 5% of the total area of the cured film) dissolves in the TMAH dissolution test C: Half of the cured coating film (About 5-50% of the total area of the cured film) is dissolved in the TMAH dissolution test D: The cured coating is completely dissolved or almost dissolved in the TMAH dissolution test
• Examples and Comparative Examples Using the following functional polysiloxane solution and curing catalyst, mix in the composition shown in Table 1 (parts by mass; polysiloxane is converted to solid content), then dilute with PGMEA so that the total solid content concentration is 20% by mass. After that, it was filtered through a membrane filter with a pore size of 0.2 ⁇ m to prepare each ultraviolet curable composition.
• Ultraviolet curable polysiloxane (A-1) PGMEA solution of the functional polysiloxane solution obtained by solvent substitution of the functional polysiloxane solution obtained in the above synthesis example (C-1) obtained in the above synthesis example PGMEA solution of the functional polysiloxane obtained in the above synthesis example (C-2) PGMEA solution of the functional polysiloxane obtained in the above synthesis example (C-3) PGMEA solution of the functional polysiloxane obtained in the above synthesis example (C-4 ) PGMEA solution of the functional polysiloxane obtained in the above synthesis example (C-5) PGMEA solution of the functional polysiloxane obtained in the above synthesis example (C-6) Functional polysiloxane obtained in the above synthesis example PGMEA solution (C-7) PGMEA solution of the functional polysiloxane obtained in the above synthesis example (C-8) PGMEA solution of the functional polysiloxane obtained in the
• Example 1 [Dielectric constant of cured organopolysiloxane (cured film)]
• the curable composition of Example 1 was poured into a Teflon cup with a diameter of 50 mm and dried at room temperature for 16 hours, followed by drying at 50° C. for 5 hours and then at 90° C. for 12 hours to give a 100 ⁇ m thick film.
• a transparent organopolysiloxane film was formed.
• This film test piece was irradiated with ultraviolet light (LED light of 365 nm, 2000 mJ/cm 2 ) and further heated in an oven at 150° C. for 30 minutes to obtain a completely cured coating film.
• LED light ultraviolet light
• Example 6 On the other hand, the same operation was performed using the curable composition of Example 6, whose main component was an ultraviolet curable organopolysiloxane consisting only of silsesquioxane units, to form an organopolysiloxane film having a thickness of 100 ⁇ m. Attempts were made, but many cracks occurred on the surface and a transparent film could not be formed.
• main component was an ultraviolet curable organopolysiloxane consisting only of silsesquioxane units
• the coating films formed from the UV-curable organopolysiloxanes of the present invention exhibit high alkali solubility, particularly organopolysiloxanes having D structural units as well as silsesquioxane units.
• Polysiloxane and curable compositions containing it had particularly excellent alkali solubility.
• the present organopolysiloxane has good UV curability.
• the cured coating film formed by ultraviolet irradiation is transparent, and in particular, the cured coating film obtained from polysiloxane having both the UV-curable group and the hydrophilic group in the D structural unit has high transparency and sufficient coating film. Shows toughness.
• branched organopolysiloxane of the present invention by adjusting the types of structural units and functional groups that make up the branched organopolysiloxane of the present invention, it is possible to adjust the refractive index of the organopolysiloxane over a wide range. It is possible to design a cured product having a desired refractive index in the composition. In particular, since branched organopolysiloxanes having trifluoro-functional structural units have a refractive index of 1.45 or less, using such branched organopolysiloxanes makes it possible to form a cured product with a low refractive index. There is an advantage that a curable composition can be designed.
• the UV-curable organopolysiloxane of the present invention and the UV-curable composition containing it as a main component have excellent UV-curing properties, and at the same time, are remarkably excellent in alkali solubility.
• the organopolysiloxane or the like is particularly suitable as a material for forming an insulating layer of a display device such as a touch panel and a display, particularly a flexible display, particularly as a patterning material and a coating material.

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• 2022
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