WO2014104195A1 - Agent d'amélioration de l'adhérence et composé silane - Google Patents

Agent d'amélioration de l'adhérence et composé silane Download PDF

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WO2014104195A1
WO2014104195A1 PCT/JP2013/084892 JP2013084892W WO2014104195A1 WO 2014104195 A1 WO2014104195 A1 WO 2014104195A1 JP 2013084892 W JP2013084892 W JP 2013084892W WO 2014104195 A1 WO2014104195 A1 WO 2014104195A1
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group
carbon atoms
integer
same
different
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PCT/JP2013/084892
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English (en)
Japanese (ja)
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一樹 上村
秀樹 片江
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大阪有機化学工業株式会社
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Priority to KR1020157020096A priority Critical patent/KR102137626B1/ko
Priority to JP2014554547A priority patent/JP6267132B2/ja
Priority to CN201380067807.0A priority patent/CN104937054B/zh
Publication of WO2014104195A1 publication Critical patent/WO2014104195A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/28—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for wrinkle, crackle, orange-peel, or similar decorative effects
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/075—Silicon-containing compounds
    • G03F7/0751—Silicon-containing compounds used as adhesion-promoting additives or as means to improve adhesion

Definitions

  • the present invention relates to an adhesion improver.
  • the present invention also relates to a novel silane compound.
  • the number of pixels of a display is increasing to 4k2k etc. with the high definition and high image quality of a flat panel display. For this reason, it is necessary to create a fine pattern.
  • a photoresist material having high photosensitivity, high heat resistance, and chemical resistance is required.
  • the capacitance type touch panel captures a change in capacitance between the fingertip and the conductive film and searches for a position.
  • a layer for reducing external impact cannot be provided unlike a resistive touch panel. For this reason, high hardness is required for the surface protective layer.
  • the materials used must have high adhesion, in addition to high photosensitivity, high heat resistance, chemical resistance, hardness, and other properties. However, sufficient adhesion cannot be obtained with current materials.
  • the present invention has been made in view of the above problems, and an object thereof is to provide a stable adhesion improving agent having adhesion improving properties and a novel silane compound.
  • the present inventors have found that a silane compound, which is a reaction product of a silicon compound having an isocyanate and a silicon compound having a specific block group, has adhesion improving properties and is stable. Further, the inventors have found a novel silane compound in the reaction product and completed the present invention. That is, the present invention is as follows.
  • the adhesion improving agent of the present invention contains a silane compound that is a reaction product of a silicon compound having an isocyanate represented by the following general formula (1) and a silicon compound represented by the following general formula (2).
  • R 1 to R 3 may be the same or different, and all or at least one is an alkoxy group having 1 to 5 carbon atoms, and the other is an alkyl group having 1 to 5 carbon atoms.
  • r is an integer of 1 to 3.
  • R 4 to R 6 may be the same or different and each represents an alkoxy group having 1 to 5 carbon atoms or an alkyl group having 1 to 5 carbon atoms.
  • B is a substituted or unsubstituted carbon group having 2 carbon atoms.
  • X is O, NH, NH—CO—NH, S.
  • s is an integer of 1 to 3.
  • the silane compound is preferably a compound represented by the following formula (3) or (4).
  • R 1 to R 3 may be the same or different, and all or at least one is an alkoxy group having 1 to 5 carbon atoms, and the other is an alkyl group having 1 to 5 carbon atoms.
  • 4 to R 6 may be the same or different and each represents an alkoxy group having 1 to 5 carbon atoms or an alkyl group having 1 to 5 carbon atoms, and A represents a substituted or unsubstituted straight chain having 2 to 18 carbon atoms.
  • a branched alkylene group which may contain a divalent or trivalent linking group, and B is a substituted or unsubstituted linear or branched alkylene group having 2 to 15 carbon atoms;
  • X may be O, NH, NH—CO—NH or S.
  • p is an integer of 0 or 1.
  • q is an integer of 1 to 3.
  • r is an integer of 1 to 3.
  • s is an integer of 1 to 3.
  • t is an integer of 1 to 3.
  • the divalent or trivalent linking group has the following formula: In the linear or branched alkylene group having 2 to 15 carbon atoms and having a linking group, which is at least one selected from the group consisting of [A1] and represented by B, It is preferably at least one selected from the group consisting of formula [B1].
  • R 7 and R 8 may be the same or different and each represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, —CH ⁇ , (R 9 and R 10 are alkyl groups having 1 to 5 carbon atoms, m3 is an integer of 1 to 5), (M4 is an integer from 1 to 5), (R 11 is an alkyl group having 1 to 5 carbon atoms) or a monovalent or divalent group represented by a cycloalkane having 3 to 6 carbon atoms which may have a substituent. When a divalent group is bonded to either R 7 or R 8 , the other is a hydrogen atom or a monovalent group. ], A substituted or unsubstituted cycloalkane having 3 to 6 carbon atoms and having at least two bonds,
  • the silane compound is preferably a silane compound represented by any one of the following formulas (5) to (8).
  • R 1 to R 3 may be the same or different, and all or at least one is an alkoxy group having 1 to 5 carbon atoms, and the other is an alkyl group having 1 to 5 carbon atoms.
  • 4 to R 6 may be the same or different and each represents an alkyl group of 1 to 5.
  • m is an integer of 2 to 18.
  • R 1 to R 3 may be the same or different, and all or at least one is an alkoxy group having 1 to 5 carbon atoms, and the other is an alkyl group having 1 to 5 carbon atoms.
  • R 4 to R 6 may be the same or different and are an alkoxy group having 1 to 5 carbon atoms or an alkyl group having 1 to 5 carbon atoms, m is an integer of 2 to 18, and n is 2 to (It is an integer of 15.)
  • R 1 to R 3 may be the same or different, and all or at least one is an alkoxy group having 1 to 5 carbon atoms, and the other is an alkyl group having 1 to 5 carbon atoms.
  • 4 to R 6 may be the same or different and are an alkoxy group having 1 to 5 carbon atoms or an alkyl group having 1 to 5 carbon atoms, m is an integer of 2 to 18, and n is 2 to (It is an integer of 15.)
  • R 1 to R 3 may be the same or different, and all or at least one is an alkoxy group having 1 to 5 carbon atoms, and the other is an alkyl group having 1 to 5 carbon atoms.
  • 4 to R 6 may be the same or different and are an alkoxy group having 1 to 5 carbon atoms or an alkyl group having 1 to 5 carbon atoms, m is an integer of 2 to 18, and n is 2 to (It is an integer of 15.)
  • the adhesion improving agent of the present invention preferably further contains a silane compound represented by the following general formula (9).
  • R 12 to R 14 may be the same or different and each represents hydroxy or an alkoxy group having 1 to 5 carbon atoms;
  • R 15 represents a carboxylic anhydride group or —CHR 16 COOH (wherein R 16 Is a carboxylic anhydride, carboxylic acid or carboxylic ester group), and
  • D is a substituted or unsubstituted linear or branched alkylene group having 2 to 10 carbon atoms, or a substituted or unsubstituted carbon number.
  • R 12 to R 14 may be the same or different and each represents hydroxy or an alkoxy group having 1 to 5 carbon atoms
  • R 15 represents a carboxylic anhydride group or —CHR 16 COOH (wherein R 16 Is a carboxylic anhydride, carboxylic acid
  • the present invention also relates to a resist material containing the adhesion improving agent.
  • the present invention further relates to a novel silane compound represented by the following general formula (3 ′) or (4 ′).
  • R 1 to R 3 may be the same or different, and all or at least one is an alkoxy group having 1 to 5 carbon atoms, and the other is an alkyl group having 1 to 5 carbon atoms.
  • 4 to R 6 may be the same or different and each represents an alkoxy group having 1 to 5 carbon atoms or an alkyl group having 1 to 5 carbon atoms, and A represents a substituted or unsubstituted straight chain having 2 to 18 carbon atoms.
  • branched alkylene group which may contain a divalent or trivalent linking group, and B is a substituted or unsubstituted linear or branched alkylene group having 2 to 15 carbon atoms;
  • X is O or NH—CO—NH, p is an integer of 0 or 1.
  • q is an integer of 1 to 3.
  • r is 1
  • S is an integer of 1 to 3.
  • s is an integer of 1 to 3.
  • t is an integer of 1 to 3.
  • the silane compound represented by the general formula (3 ′) or (4 ′) of the present invention in the linear or branched alkylene group having 2 to 18 carbon atoms having a linking group represented by A, 2
  • the valent or trivalent linking group is preferably at least one selected from the group consisting of the following formula [A1], and is a straight chain having 2 to 15 carbon atoms having a linking group represented by B or
  • the divalent linking group is preferably at least one selected from the group consisting of the following formula [B1].
  • R 7 and R 8 may be the same or different and each represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, —CH ⁇ , (R 9 and R 10 are alkyl groups having 1 to 5 carbon atoms, m3 is an integer of 1 to 5), (M4 is an integer from 1 to 5), (R 11 is an alkyl group having 1 to 5 carbon atoms) or a monovalent or divalent group represented by a cycloalkane having 3 to 6 carbon atoms which may have a substituent. When a divalent group is bonded to either R 7 or R 8 , the other is a hydrogen atom or a monovalent group. ], A substituted or unsubstituted cycloalkane having 3 to 6 carbon atoms and having at least two bonds,
  • the silane compound represented by the general formula (3 ′) or (4 ′) of the present invention is preferably a silane compound represented by the following general formula (10).
  • R 1 to R 3 may be the same or different, and all or at least one is an alkoxy group having 1 to 5 carbon atoms, and the other is an alkyl group having 1 to 5 carbon atoms.
  • 4 to R 6 may be the same or different and are an alkoxy group having 1 to 5 carbon atoms or an alkyl group having 1 to 5 carbon atoms, m is an integer of 2 to 18, and n is 2 to And is an integer of 15.
  • X is O or NH—CO—NH.
  • the adhesion improver of the present invention is a silane compound that is a reaction product of a silicon compound having an isocyanate and a silicon compound having a specific block group.
  • a silane compound that is a reaction product of a silicon compound having an isocyanate and a silicon compound having a specific block group.
  • novel silane compound of the present invention can impart adhesion and stability to a resin, paint, resist material, coating agent, etc. when used in combination with a resin, paint, resist material, coating agent, or the like.
  • the molded product produced by adding the silane compound of the present invention can avoid the occurrence of seizure or the like.
  • FIG. 1 is an IR chart showing the completion of the reaction in Example 1.
  • FIG. 2 is an NMR chart of the reaction product of Example 1.
  • the adhesion improving agent of the present invention is a silane compound that is a reaction product of a silicon compound having an isocyanate and a silicon compound having a specific block group. Specifically, it is as follows.
  • the adhesion improving agent of the present invention contains a silane compound that is a reaction product of a silicon compound having an isocyanate represented by the following general formula (1) and a silicon compound represented by the following general formula (2).
  • the compound represented by the general formula (1) is a compound containing q silicon-containing groups and r isocyanate groups in the molecule.
  • R 1 to R 3 may be the same or different, and all or at least one is an alkoxy group having 1 to 5 carbon atoms, and the other is an alkyl group having 1 to 5 carbon atoms. is there.
  • alkoxy group having 1 to 5 carbon atoms examples include methoxy group, ethoxy group, 1-propoxy group, 2-propoxy group, 1-butoxy group, 2-methylpropoxy group, 2-butoxy group, 1,1-dimethylethoxy.
  • alkyl group having 1 to 5 carbon atoms examples include methyl group, ethyl group, 1-propyl group, 2-propyl group, 1-butyl group, 2-methylpropyl group, 2-butyl group, and 1,1-dimethylethyl.
  • A is a substituted or unsubstituted linear or branched alkylene group having 2 to 18 carbon atoms.
  • the carbon number of the linear or branched alkylene group is preferably 2 to 12, more preferably 2 to 6.
  • Examples of the substituent of a linear or branched alkylene group having 2 to 18 carbon atoms include an ester group to which an alkyl group having 1 to 5 carbon atoms is bonded.
  • A may contain at least one divalent or trivalent linking group. Examples of the divalent or trivalent linking group include those represented by the following formula [A1].
  • R 7 and R 8 may be the same or different and each represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, —CH ⁇ , (R 9 and R 10 are alkyl groups having 1 to 5 carbon atoms, m3 is an integer of 1 to 5), (M4 is an integer from 1 to 5), (R 11 is an alkyl group having 1 to 5 carbon atoms) or a monovalent or divalent group represented by a cycloalkane having 3 to 6 carbon atoms which may have a substituent.
  • R 7 or R 8 When a divalent group is bonded to either R 7 or R 8 , the other is a hydrogen atom or a monovalent group. ], A substituted or unsubstituted cycloalkane having 3 to 6 carbon atoms and having at least two bonds,
  • the alkyl group having 1 to 5 carbon atoms is the same as that exemplified in the general formula (1).
  • Examples of the aryl group having 6 to 12 carbon atoms include phenyl group, benzyl group, and tolyl group.
  • Examples of the cycloalkane having 3 to 6 carbon atoms include cyclopropane, cyclobutane, cyclopentane, and cyclohexane.
  • the isocyanate group or silicon atom is bonded to A.
  • A contains one or more trivalent linking groups [A1]
  • A1 trivalent linking groups
  • a compound having a plurality of isocyanate groups in the molecule or a compound containing a plurality of silicon atoms in the molecule can be obtained.
  • a trivalent linking group is included, a divalent linking group is formed by bonding a group that does not participate in the reaction, such as a methyl group or a cyano group, to the end of the one linking group. In some cases.
  • Q is an integer of 1 to 3, preferably 1.
  • r is an integer of 1 to 3, preferably 1.
  • the compound represented by the general formula (2) is a compound having s groups containing silicon and t XH groups in the molecule.
  • R 4 to R 6 may be the same or different and each represents an alkoxy group having 1 to 5 carbon atoms or an alkyl group having 1 to 5 carbon atoms.
  • Examples of the alkoxy group having 1 to 5 carbon atoms or the alkyl group having 1 to 5 carbon atoms are the same as those exemplified above for R 1 to R 3 .
  • B is a substituted or unsubstituted linear or branched alkylene group having 2 to 15 carbon atoms.
  • the number of carbon atoms of the linear or branched alkylene group is preferably 2 to 10, more preferably 2 to 6.
  • B may contain at least one divalent linking group. Examples of the divalent linking group include those represented by the following formula [B1].
  • X is O, NH, NH—CO—NH, S.
  • X group or silicon atom is bonded to B, or X group and silicon atom are directly bonded.
  • the second or more X groups are bonded to the above [B1], or the substituent [B1] itself is an NH—CO—NH group.
  • the second or more silicon atoms are bonded to the above [B1] or are a substituent of a linear or branched alkylene group.
  • P is an integer of 0 or 1.
  • s is an integer of 1 to 3, and is preferably 1.
  • t is an integer of 1 to 3, and is preferably 1.
  • the silane compound according to the present invention is a reaction product of a silicon compound having an isocyanate represented by the general formula (1) and a silicon compound represented by the general formula (2).
  • This reaction is a nucleophilic addition reaction of the X group of the silicon compound represented by the general formula (2) to the isocyanate group of the silicon compound having an isocyanate represented by the general formula (1).
  • the reaction product may have all isocyanate groups blocked with X groups. That is, it may be a reaction product of a silicon compound having a plurality of isocyanate groups and a silicon compound having a plurality of X groups.
  • the solvent may or may not be used, and is not particularly limited.
  • a solvent for example, ethers such as diethyl ether, ethyl methyl ether, tetrahydrofuran and dioxane, halogenated hydrocarbons such as chloroform and dichloromethane, amides such as dimethylformamide, ethyl acetate, methyl acetate, butyl acetate and the like Esters, N-methylpyrrolidone and the like can be used.
  • the use ratio of the silicon compound having the isocyanate represented by the general formula (1) and the silicon compound represented by the general formula (2) is completely different from X of the silicon compound in which the isocyanate is represented by the general formula (2). If it can respond to, there will be no restriction
  • the amount of X used may be large or small relative to 1 mole of isocyanate. When the amount of X used is large relative to 1 mole of isocyanate, a compound represented by formula (3) or (4) is obtained. When the amount of X used is small relative to 1 mole of isocyanate, active hydrogen in the silicon compound represented by the general formula (3) or (4) remains in the reaction system. By reacting, a compound having a structure in which the isocyanate group disappears is obtained.
  • the use ratio of the silicon compound having the isocyanate represented by the general formula (1) and the silicon compound represented by the general formula (2) is particularly limited as long as the isocyanate completely reacts with X of the silicon compound.
  • X is 1.00 to 6.00 moles, preferably 1.00 to 1.50 moles, more preferably 1.00 to 1.20 moles per mole of isocyanate. If X is less than 1.00 mol with respect to 1 mol of isocyanate, the reaction between isocyanate and X cannot be carried out completely, which is not preferable. When X is more than 6.00 moles with respect to 1 mole of isocyanate, an unreacted silicon compound represented by the general formula (2) remains, which is not preferable.
  • the reaction temperature is 30 to 90 ° C, preferably 40 to 80 ° C, more preferably 50 to 70 ° C.
  • the reaction time is usually 1 minute to 2 days, particularly 30 minutes to 3 hours.
  • IR infrared spectroscopy
  • the silane compound which is a reaction product of the silicon compound having an isocyanate represented by the general formula (1) and the silicon compound represented by the general formula (2) is, for example, the following formula (3) or (4) It is preferable that it is a compound represented by these.
  • R 1 to R 3 , R 4 to R 6 , A, B, X, p, q, r, and s are the same as those shown in the general formulas (1) and (2).
  • the silane compound represented by the general formula (3) is obtained by the following reaction formula.
  • R 1 to R 3 , R 4 to R 6 , A, B, X, p, q, s, and t are the same as those shown in the general formulas (1) and (2).
  • the silane compound represented by the general formula (4) is obtained by the following reaction formula.
  • the silane compound is a silane compound represented by any one of the following formulas (5) to (8).
  • R 1 to R 3 are the same as those shown in the chemical formula (1).
  • R 4 to R 6 may be the same or different and are 1 to 5 alkyl groups. The alkyl group having 1 to 5 carbon atoms is the same as described above.
  • m is an integer of 2 to 18, preferably 2 to 8, particularly preferably an integer of 2 to 4.
  • R 1 to R 3 and R 4 to R 6 are the same as those shown in the chemical formulas (1) and (2).
  • n is an integer of 2 to 15, preferably 2 to 8, particularly preferably an integer of 2 to 4.
  • R 1 to R 3 , R 4 to R 6 , m, and n are the same as those in the general formula (6).
  • R 1 to R 3 , R 4 to R 6 , m, and n are the same as those in the general formula (6).
  • the adhesion improver of the present invention can be used by adding to a material used for applications requiring adhesion and stability. Specifically, it may be used by adding to a resist material, a passivation film, an overcoat agent, an insulating film material, OP varnish, ink, or the like.
  • the adhesion improver of the present invention can further contain a silane compound represented by the following general formula (9).
  • R 12 to R 14 may be the same or different and each represents hydroxy or an alkoxy group having 1 to 5 carbon atoms;
  • R 15 represents a carboxylic anhydride group or —CHR 16 COOH (where R 16 represents D is a substituted or unsubstituted C2-C10 linear or branched alkylene group, or a substituted or unsubstituted carbon, or a carboxylic anhydride group, a carboxylic acid group or a carboxylic acid ester group. It is an alkylene group having at least one double or straight chain or branched chain having a number of 2 to 10. ]
  • R 12 to R 14 may be the same or different and are hydroxy or an alkoxy group having 1 to 5 carbon atoms.
  • the alkoxy group having 1 to 5 carbon atoms is the same as that shown in the above formula (1), and a methoxy group or an ethoxy group is preferable.
  • R 15 is a carboxylic anhydride group or —CHR 16 COOH (wherein R 16 is a carboxylic anhydride group, a carboxylic acid group or a carboxylic ester group), and a carboxylic anhydride group It is preferable that
  • Examples of the carboxylic anhydride constituting the carboxylic anhydride group include succinic anhydride, maleic anhydride, and glutaric anhydride, and succinic anhydride is preferable.
  • the carboxylic acid ester group is not particularly limited, and examples thereof include a linear or branched ester group with a C 1-5 alcohol, a polyethylene chain, a polypropylene chain, and the like, and a (meth) acryloyloxy group. It may have a reactive group such as a (meth) acrylamide group.
  • D is a substituted or unsubstituted linear or branched alkylene group having 2 to 10 carbon atoms, or a substituted or unsubstituted linear or branched chain group having 2 to 10 carbon atoms.
  • An alkylene group having two double bonds, and the alkylene chain preferably has 2 to 5 carbon atoms, more preferably 2 or 3.
  • Specific examples of the general formula (9) include trimethoxysilylpropyl succinic anhydride, triethoxysilylpropyl succinic anhydride, trimethoxysilylbutyl succinic anhydride, triethoxysilylbutyl succinic anhydride, 3- [6- (tri Trimethoxysilylhexynyl succinic anhydride such as methoxysilyl) -2-hexen-1-yl] succinic anhydride, 2-methyl-3- (triethoxysilyl) propyl succinic anhydride, 3- [10- (trimethoxy Silyl) -2-decen-1-yl] succinic anhydride, tetrahydro-2,5-dioxo- ⁇ - [2- (triethoxysilyl) ethyl] -3-furan acetic acid, 3-trimethoxysilylpropyl glutaric anhydride , 3-triethoxysily
  • the ring is opened by moisture in the system to generate a carboxyl group.
  • a scheme in the case where the acid anhydride group is succinic anhydride is shown below, but the same applies to other acid anhydride groups.
  • the R 17 group represents a hydroxyl group derived from a carboxyl group produced by hydrolysis, or an alkoxy group produced by alcoholysis with an alcohol produced in the reaction system by hydrolysis, such as an alcohol having 1 to 5 carbon atoms. Show. Such a ring-opened product is also included in the compound of the general formula (9). (In the formula, R 17 represents a hydroxyl group or an alkoxy group having 1 to 5 carbon atoms, and the alkoxy group having 1 to 5 carbon atoms is the same as that represented by the above formula (1).)
  • the adhesiveness-improving agent of the present invention can further improve the adhesiveness by including the silane compound represented by the general formula (9).
  • the adhesion improver of the present invention When the adhesion improver of the present invention is added to a resist material and used, it can be used as a protective film (resist) when processing such as sand blasting, ion implantation, etching, etc. in various manufacturing processes. Since the resist material to which the adhesion improver of the present invention is added is excellent in adhesion and developability, it is possible to produce a highly functional device.
  • the resist may be a negative resist or a positive resist.
  • the addition amount at the time of adding the adhesion improving agent of the present invention to the resist material is not particularly limited, and may be appropriately determined according to the material such as the resist material and the purpose of use.
  • the resist material usually contains a polymerizable compound (monomer or oligomer), a binder polymer, a surfactant, a photopolymerization initiator, a solvent, and the like. Moreover, you may add an inorganic filler, a ultraviolet absorber, dye, a pigment, etc. as needed.
  • the adhesion improver of the present invention is used by adding to such a resist material.
  • the resist material of the present invention contains at least one polymerizable compound (monomer or oligomer) having at least two ethylenically unsaturated bonds.
  • the polymerizable compound having at least one ethylenically unsaturated bond is not particularly limited as long as it is capable of radical polymerization.
  • the polymerizable compound only needs to have at least one ethylenically unsaturated bond, for example, a compound having one ethylenically unsaturated bond in the molecule and two ethylenically unsaturated bonds in the molecule. Either a compound or a compound having three or more ethylenically unsaturated bonds in the molecule may be used.
  • the compound having two ethylenically unsaturated bonds in the molecule include a bisphenol A di (meth) acrylate compound, a hydrogenated bisphenol A di (meth) acrylate compound, and a urethane bond in the molecule.
  • Examples include di (meth) acrylate compounds, polyalkylene glycol di (meth) acrylate compounds, trimethylolpropane di (meth) acrylate, and 1,6-hexanediol diacrylate.
  • 2,2-bis (4- (methacryloxypentaethoxy) phenyl) propane a compound having two ethylenically unsaturated bonds in its molecule
  • BPE-500 trade name, manufactured by Shin-Nakamura Chemical Co., Ltd.
  • FA-321M trade name, manufactured by Hitachi Chemical Co., Ltd.
  • 2,2-bis (4- (methacryloxypentadecaethoxy) phenyl) propane is BPE-1300 (new It is commercially available as a product name of Nakamura Chemical Co., Ltd.
  • the compound having two ethylenically unsaturated bonds in the molecule is used alone or in any combination of two or more.
  • Examples of the compound having one ethylenically unsaturated bond in the molecule include nonylphenoxypolyethyleneoxyacrylate, phthalic acid compounds, and (meth) acrylic acid alkyl esters.
  • Nonylphenoxypolyethyleneoxyacrylate includes nonylphenoxytriethyleneoxyacrylate, nonylphenoxytetraethyleneoxyacrylate, nonylphenoxypentaethyleneoxyacrylate, nonylphenoxyhexaethyleneoxyacrylate, nonylphenoxyheptaethyleneoxyacrylate, nonylphenoxyoctaethyleneoxyacrylate Nonylphenoxynonaethyleneoxyacrylate, nonylphenoxydecaethyleneoxyacrylate, nonylphenoxyundecaethyleneoxyacrylate, and the like. These may be used alone or in any combination of two or more.
  • phthalic acid compounds examples include ⁇ -chloro- ⁇ -hydroxypropyl- ⁇ '-(meth) acryloyloxyethyl-o-phthalate, ⁇ -hydroxyethyl- ⁇ '-(meth) acryloyloxyethyl-o- Phthalate, ⁇ -hydroxypropyl- ⁇ ′-(meth) acryloyloxyethyl-o-phthalate, and the like, among others, ⁇ -chloro- ⁇ -hydroxypropyl- ⁇ ′-(meth) acryloyloxyethyl-o-phthalate Is preferred.
  • ⁇ -Chloro- ⁇ -hydroxypropyl- ⁇ '-methacryloyloxyethyl-o-phthalate is commercially available as FA-MECH (trade name, manufactured by Hitachi Chemical Co., Ltd.). These can be used alone or in combination of two or more.
  • Examples of the compound having three or more ethylenically unsaturated bonds in the molecule include trimethylolpropane tri (meth) acrylate, EO-modified trimethylolpropane tri (meth) acrylate (one having a total number of repeating oxyethylene groups of 1 to 5).
  • the content of the polymerizable compound in the resist material of the present invention is not particularly limited, but is preferably 30 to 70 parts by mass, and 35 to 65 parts by mass in 100 parts by mass of the total amount of the binder polymer and polymerizable compound described below. More preferably, the amount is 35 to 60 parts by mass.
  • this content is 30 parts by mass or more, sufficient sensitivity and resolution tend to be obtained, and when it is 70 parts by mass or less, film formability tends to be good, and a good resist shape is obtained. There is a tendency to become easily.
  • the resist material of the present invention contains at least one binder polymer.
  • a commonly used binder polymer can be used without any particular limitation. Specific examples include acrylic resins, styrene resins, epoxy resins, amide resins, amide epoxy resins, alkyd resins, and phenol resins. Among these, acrylic resins are preferable from the viewpoint of alkali developability.
  • a binder polymer can be used individually by 1 type or in combination of 2 or more types.
  • the binder polymer can be produced, for example, by radical polymerization of a polymerizable monomer.
  • the polymerizable monomer include polymerizable styrene derivatives having a substituent on the ⁇ -position or aromatic ring such as styrene, vinyltoluene, and ⁇ -methylstyrene; acrylamide such as diacetone acrylamide; Esters of vinyl alcohol such as acrylonitrile and vinyl-n-butyl ether; (meth) acrylic acid alkyl ester, (meth) acrylic acid benzyl ester, (meth) acrylic acid tetrahydrofurfuryl ester, (meth) acrylic acid glycidyl ester, 2 , 2,2-trifluoroethyl (meth) acrylate, (meth) acrylic esters such as 2,2,3,3-tetrafluoropropyl (meth) acrylate; (meth) acrylic acid, ⁇ -bromoacrylic acid,
  • the (meth) acrylic acid alkyl ester may be a compound in which an alkyl group is substituted with a hydroxyl group, an epoxy group, a halogen group or the like.
  • Examples of the monomer of (meth) acrylic acid alkyl ester include (meth) acrylic acid methyl ester, (meth) acrylic acid ethyl ester, (meth) acrylic acid propyl ester, (meth) acrylic acid butyl ester, (meta ) Acrylic acid pentyl ester, (meth) acrylic acid hexyl ester, (meth) acrylic acid heptyl ester, (meth) acrylic acid octyl ester, (meth) acrylic acid 2-ethylhexyl ester, (meth) acrylic acid nonyl ester, (meth) ) Aromatic ring-containing (meth) acrylates such as alkyl (meth) acrylates such as decyl acrylate, undecyl (meth) acrylate, dodecyl (meth) acrylate, phenyl (meth) acrylate, and benzyl (meth) acrylate , Hydroxy Ethyl (me
  • the binder polymer in the present invention preferably contains a carboxyl group from the viewpoint of alkali developability.
  • the binder polymer containing a carboxyl group can be produced, for example, by radical polymerization of a polymerizable monomer having a carboxyl group and another polymerizable monomer.
  • Examples of the polymerizable monomer having a carboxyl group include (meth) acrylic acid, (meth) acrylic caprolactone adduct, (meth) acryloylethyl monophthalate, (meth) acryloylethyl monohexahydrophthalate, (meth) Acryloylethyl monotetrahydrophthalate and the like are preferable, and methacrylic acid is more preferable.
  • binder polymers are used alone or in combination of two or more.
  • a binder polymer in the case of using two or more types in combination, for example, two or more types of binder polymers comprising different copolymerization components, two or more types of binder polymers having different weight average molecular weights, and two or more types of binder polymers having different degrees of dispersion are used. Examples thereof include a binder polymer.
  • the ratio of the resin for the binder polymer to the total sum of the resist materials is in the range of 20 to 90% by mass, preferably 30 to 70% by mass.
  • the resist pattern formed by exposure and development is 20% by mass or more and 90% by mass or less from the viewpoint that resist characteristics, for example, sufficient resistance and the like in tenting, etching, and various plating processes.
  • Photopolymerization initiator As a photoinitiator used for the resist material of this invention, it is good to use what contains at least 1 sort (s) of an imidazole dimer as a photoinitiator.
  • the imidazole dimer as a photopolymerization initiator include 2- (o-chlorophenyl) -4,5-diphenylimidazole dimer, 2- (o-fluorophenyl) -4,5-diphenylimidazole dimer.
  • a combination with a pyrazoline compound such as 1-phenyl-3- (4-tert-butyl-styryl) -5- (4-tert-butyl-phenyl) -pyrazoline is a preferred embodiment.
  • the photopolymerization initiator is a compound that is activated by various actinic rays such as ultraviolet rays and starts polymerization.
  • Other photopolymerization initiators include quinones such as 2-ethylanthraquinone, 2-tert-butylanthraquinone, aromatic ketones such as benzophenone, benzoin and benzoin ethers such as benzoin methyl ether and benzoin ethyl ether.
  • Acridine compounds such as 9-phenylacridine, benzyldimethyl ketal, benzyldiethyl ketal, 2,4-trichloromethyl- (4 ′′ -methoxyphenyl) -6-triazine, 2,4-trichloromethyl- (4′-methoxy) Naphthyl) -6-triazine, 2,4-trichloromethyl- (piperonyl) -6-triazine, triazines such as 2,4-trichloromethyl- (4′-methoxystyryl) -6-triazine, 2-methyl-1 -(4-Methylthiophenyl -2-morpholinopropan-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone, 2-dimethylamino-1- (4-morpholinophenyl) -but
  • thioxanthones such as thioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone and tertiary amine compounds such as dimethylaminobenzoic acid alkyl ester compounds.
  • oxime esters such as 1-phenyl-1,2-propanedione-2-O-benzoyloxime and 1-phenyl-1,2-propanedione-2- (O-ethoxycarbonyl) oxime.
  • N-aryl- ⁇ -amino acid compounds can also be used, and among these, N-phenylglycine is particularly preferred.
  • the ratio of the photopolymerization initiator contained in the resist material of the present invention is 0.01 to 30% by mass. If this ratio is less than 0.01% by mass, sufficient sensitivity cannot be obtained. On the other hand, if this ratio exceeds 30% by mass, fogging due to diffraction of light passing through the photomask at the time of exposure tends to occur, and as a result, resolution is deteriorated.
  • the content is more preferably 0.1 to 15% by mass, and further preferably 0.1 to 10% by mass.
  • the resist material of the present invention can further contain various additives.
  • Additives include dyes, photochromic agents, thermochromic inhibitors, plasticizers, hydrogen donors, color formers, pigments, fillers, antifoaming agents, flame retardants, adhesion promoters, leveling agents, peeling accelerators, An antioxidant, a fragrance
  • the resist material of the present invention can contain a solvent as necessary. It does not restrict
  • alcohols such as methanol and ethanol
  • ketones such as acetone and methyl ethyl ketone
  • glycol acetates such as methyl cellosolve and ethyl cellosolve
  • hydrocarbons such as toluene
  • protic polar solvents examples include protic polar solvents, ether acetates such as propylene glycol monomethyl ether 2-acetate and methyl methoxypropionate, and cyclic ketones such as cyclohexanenone.
  • solvents are used alone or as a mixed solvent combining two or more kinds.
  • the content of the solvent is appropriately selected according to the purpose. For example, a solution having a solid content of about 30 to 60% by mass can be obtained.
  • the solid content is the total amount of nonvolatile components in the resist material.
  • the resist material can be used for forming a resist layer as follows, for example.
  • a resist layer which is a coating film of the resist material, can be formed on the support by applying the resist material on the surface of a support such as a support film, a metal plate, or glass, which will be described later, and drying.
  • a polymer film having heat resistance and solvent resistance such as polyethylene terephthalate, polypropylene, polyethylene, and polyester can be used.
  • the metal plate include iron alloys such as copper, copper alloys, nickel, chromium, iron, and stainless steel, preferably copper, copper alloys, iron alloys, and the like.
  • the thickness of the resist layer to be formed varies depending on its use, but is preferably about 0.1 ⁇ m to 100 ⁇ m after drying.
  • the surface (surface) opposite to the surface facing the support of the resist layer may be covered with a protective film.
  • the protective film include polymer films such as polyethylene and polypropylene.
  • the photosensitive element is placed on a circuit forming substrate, and the photosensitive resin composition layer in the photosensitive element is in close contact with the circuit forming substrate. And (ii) at least a part of the photosensitive resin composition layer is irradiated with an actinic ray by a direct drawing method to photocure the exposed portion to be photocured. And (iii) a developing step of removing the unexposed portion of the photosensitive resin composition layer from the circuit forming substrate by development, and including other steps as necessary. Composed.
  • novel silane compound (3 ′) or (4 ′) is preferably a compound represented by the following general formula (10).
  • R 1 ⁇ R 3 are the same as R 1 ⁇ R 3 in the formula (3 ') or (4').
  • R 4 ⁇ R 6 are the same as R 4 ⁇ R 6 in the formula (3 ') or (4').
  • M is an integer of 2 to 18, preferably 2 to 8, particularly preferably an integer of 2 to 4.
  • n is an integer of 2 to 15, preferably 2 to 8, particularly preferably an integer of 2 to 4.
  • X is the same as in the above formula (3 ') or (4').
  • Preferred examples of the compound represented by the general formula (10) include compounds represented by the above formulas (5) and (7).
  • novel silane compound of the present invention can be used together with resins, paints, resist materials, coating agents and the like.
  • the addition amount is not particularly limited, and may be appropriately determined according to the material such as resin, paint, resist material, coating agent and the purpose of use, and all the explanations given above in the adhesion improver of the present invention are all novel of the present invention. This also applies to the use of silane compounds.
  • Example 1 In a reaction vessel equipped with a stirrer, a reflux condenser, a dropping funnel, and a thermometer, 100 parts by mass of isocyanatepropyltriethoxysilane (KBM9007, manufactured by Shin-Etsu Chemical Co., Ltd.) and 485 parts by mass of N-methylpyrrolidone (NMP) were added. 108 parts by mass of ureidopropyltrimethoxysilane (T1915, manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise to the mixed liquid while stirring. Thereafter, the mixture was raised to 65 ° C. and reacted for 2 days while maintaining this temperature. Completion of the reaction was confirmed by disappearance of isocyanate peak using IR. The solid content concentration of the obtained solution was 30.0% by mass.
  • KBM9007 isocyanatepropyltriethoxysilane
  • NMP N-methylpyrrolidone
  • FIG. 1 is an IR chart showing the completion of the reaction in Example 1. This confirmed that the isocyanate group had disappeared.
  • FIG. 2 is an NMR chart of the reaction product of Example 1.
  • Example 2 In a reaction vessel equipped with a stirrer, a reflux condenser, a dropping funnel, and a thermometer, 100 parts by mass of isocyanate propyltriethoxysilane (KBM9007, manufactured by Shin-Etsu Chemical Co., Ltd.) and 336 parts by mass of N-methylpyrrolidone (NMP) were added. 44 parts by mass of trimethylsilanol (LS-310, manufactured by Shin-Etsu Chemical Co., Ltd.) was added dropwise to the mixed liquid with stirring. Thereafter, the mixture was raised to 65 ° C. and reacted for 2 hours while maintaining this temperature. Completion of the reaction was confirmed by disappearance of isocyanate peak using IR. The solid content concentration of the obtained solution was 30% by mass.
  • Example 3 In a reaction vessel equipped with a stirrer, a reflux condenser, a dropping funnel, and a thermometer, 100 parts by mass of isocyanatepropyltriethoxysilane (KBM9007, manufactured by Shin-Etsu Chemical Co., Ltd.) and 463 parts by mass of N-methylpyrrolidone (NMP) were added. To the mixed solution, 87 parts by mass of aminopropyltrimethoxysilane (KBM-903, manufactured by Shin-Etsu Chemical Co., Ltd.) was added dropwise with stirring. Thereafter, the mixture was raised to 65 ° C. and reacted for 3 hours while maintaining this temperature. Completion of the reaction was confirmed by disappearance of isocyanate peak using IR. The solid content concentration of the obtained solution was 30% by mass.
  • Example 4 In a reaction vessel equipped with a stirrer, a reflux condenser, a dropping funnel, and a thermometer, 100 parts by mass of isocyanate propyltriethoxysilane (KBM9007, manufactured by Shin-Etsu Chemical Co., Ltd.) and 455 parts by mass of N-methylpyrrolidone (NMP) were added. To the mixed solution, 95 parts by mass of mercaptopropyltrimethoxysilane (KBM-803, manufactured by Shin-Etsu Chemical Co., Ltd.) was added dropwise with stirring. Thereafter, the mixture was raised to 65 ° C. and reacted for 2 hours while maintaining this temperature. Completion of the reaction was confirmed by disappearance of isocyanate peak using IR. The solid content concentration of the obtained solution was 30% by mass.
  • Example 5 In a reaction vessel equipped with a stirrer, a reflux condenser, a dropping funnel, and a thermometer, 100 parts by mass of isocyanate propyltriethoxysilane (KBM9007, manufactured by Shin-Etsu Chemical Co., Ltd.) and 445 parts by mass of N-methylpyrrolidone (NMP) were added. To the mixed liquid, 91 parts by mass of ureidopropyltrimethoxysilane (T1915, manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise with stirring. Thereafter, the mixture was raised to 65 ° C. and reacted for 2 days while maintaining this temperature. Completion of the reaction was confirmed by disappearance of isocyanate peak using IR. The solid content concentration of the obtained solution was 30% by mass.
  • KBM9007 isocyanate propyltriethoxysilane
  • NMP N-methylpyrrolidone
  • Example 3 A silane compound was obtained in the same manner as in Example 1 except that 42 parts by mass of methyl ethyl ketone oxime was used instead of 108 parts by mass of ureidopropyltrimethoxysilane (T1915, manufactured by Tokyo Chemical Industry Co., Ltd.).
  • DPHA dipentaerythritol hexaacrylate
  • methacrylic acid copolymer produced in Synthesis Example 1 as a binder polymer
  • silicone as a surfactant
  • Surfactant FZ-2122 silicone oil, manufactured by Toray Dow Corning
  • PGMAc 1-methoxypropyl-2-acetate
  • cyclohexanone anone, DOMO CHEMICALS
  • IRGACURE907 2-methyl-1- (4-methylthio) phenyl) -2-morpholinopropan-1-one
  • a resist material was prepared by dissolving in a solvent.
  • Example 11 instead of 8 parts by mass of the silane compound of Example 1, 3 parts by mass of the silane compound described in Example 1 and 5 of 3-trimethoxysilylpropyl succinic anhydride (X-12-967C, manufactured by Shin-Etsu Chemical Co., Ltd.) A resist material was prepared in the same manner as in Example 10 except that parts by mass were used.
  • VHR Voltage Holding Ratio
  • the surface of the test substrate was cut into grids at 1 mm intervals.
  • a cellophane tape was affixed to this surface and rubbed tightly with a nail, and then the cellophane tape was peeled off at a stretch and the adhesion was observed with a microscope.
  • evaluation of adhesiveness was determined as follows. ⁇ : No tape peeling (adhesion rate 100%). ⁇ : Tape partially peeled off (adhesion rate 30 to 99%) X: Most of the tape peeled off (adhesion rate 0 to 29%).
  • the surface of the test substrate was cut into grids at 1 mm intervals.
  • a cellophane tape was affixed to this surface and rubbed tightly with a nail, and then the cellophane tape was peeled off at a stretch and the adhesion was observed with a microscope.
  • evaluation of high temperature, high humidity adhesiveness was judged as follows. ⁇ : No tape peeling (adhesion rate 100%). ⁇ : Tape partially peeled off (adhesion rate 30 to 99%) ⁇ : Most of the tape is peeled off (adhesion rate 0 to 29%)
  • Viscosity stability of resist over time The viscosity change of the prepared resist solution after aging for 50 days at room temperature was measured.
  • ⁇ Viscosity increase rate of 5% or less compared to formulation
  • ⁇ Viscosity increase rate of 5% to 20% compared to formulation
  • ⁇ Viscosity increase rate of 20% or more compared to formulation
  • the resist materials of the above examples and comparative examples were spin-coated so as to have a film thickness of 2 ⁇ m, pre-baked at 90 ° C. for 2 minutes, and then irradiated with ultraviolet rays of 100 J / m. 2 irradiation, and then post-baked at 230 ° C. for 18 minutes.
  • this coated substrate was bonded to another glass substrate having an ITO film formed on the surface, a liquid crystal cell was prepared by injecting liquid crystal between the substrates, and annealed at 100 ° C. for 1 hour. With respect to the obtained liquid crystal cell, the voltage holding ratio was measured under the conditions of 60 ° C., voltage load time 60 microseconds, voltage 5 V, and low-pass filter 2 MHz.
  • Table 1 below shows the results of adhesion, stability, and VHR of Examples 6 to 10 and Comparative Examples 4 to 6.
  • the silane compound according to the present invention is excellent in adhesion and stability.
  • Comparative Examples 4 and 5 using only the conventional silane coupling agent it can be seen that the adhesion and stability are not balanced. Moreover, it turns out that it is inferior to all of adhesiveness, stability, and VHR in the comparative example 6 whose compound which blocks a silane coupling agent is not a silicon compound represented by General formula (2).
  • ⁇ Patterning development adhesion> A resist material was applied onto the test substrate by spin coating so that the coating film thickness was 3.5 to 4.0 ⁇ m, and was allowed to stand for 120 seconds. This was pre-baked on a hot plate at 90 ° C. for 120 seconds. This test substrate was exposed to ultraviolet rays through a 10 ⁇ m square dot mask at an exposure amount of 100 mJ / cm 2 . Next, development was performed for 60 seconds using a 0.1% by weight aqueous solution of potassium hydroxide to prepare a test substrate having a dot pattern of 10 ⁇ m square. The adhesion of the photo spacer formed on the developed substrate was observed with a microscope. The development adhesion is evaluated as follows.
  • ⁇ No peeled dot pattern (adhesion rate 100%). ⁇ : Partially peeled dot pattern present (adhesion rate 30 to 99%). ⁇ : Most of the peeled dot pattern is present (adhesion rate 0 to 29%).
  • the post-baked substrate was treated with an acid and alkali resistance test solution, and the treated substrate was observed with a microscope to observe peeling and the like.
  • the chemical resistance test adhesion was evaluated as follows. ⁇ : No peeling dot pattern (adhesion rate 100%). ⁇ : Partially peeled off and dot pattern present (adhesion rate of 30 to 99%). ⁇ : Most peeled dot patterns are present (adhesion rate 0 to 29%).
  • the adhesion improver according to the present invention is excellent in adhesion and durability even in pattern formation.
  • the silane compound of the present invention gives adhesion and stability to resins, paints, resist materials, coating agents, etc., when used in combination with resins, paints, resist materials, coating agents, etc. I found out that I can do it. Further, it has been found that the molded product produced by adding the silane compound of the present invention can avoid the occurrence of image sticking even when used in a liquid crystal display element.

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Abstract

La présente invention concerne un agent d'amélioration de l'adhérence qui a une propriété d'amélioration de l'adhérence et est stable. L'agent d'amélioration de l'adhérence est caractérisé en ce qu'il comprend un composé silane qui est un produit de réaction d'un composé du silicium contenant un isocyanate représenté par la formule générale (1) avec un composé du silicium représenté par la formule générale (2). La présente invention concerne également un nouveau composé silane représenté par la formule générale (3') ou (4').
PCT/JP2013/084892 2012-12-28 2013-12-26 Agent d'amélioration de l'adhérence et composé silane WO2014104195A1 (fr)

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TW201441239A (zh) 2014-11-01
JP6267132B2 (ja) 2018-01-24
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CN104937054A (zh) 2015-09-23
KR102137626B1 (ko) 2020-07-24

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