WO2015093510A1 - 透明導電膜用保護膜形成組成物 - Google Patents
透明導電膜用保護膜形成組成物 Download PDFInfo
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- WO2015093510A1 WO2015093510A1 PCT/JP2014/083349 JP2014083349W WO2015093510A1 WO 2015093510 A1 WO2015093510 A1 WO 2015093510A1 JP 2014083349 W JP2014083349 W JP 2014083349W WO 2015093510 A1 WO2015093510 A1 WO 2015093510A1
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- transparent conductive
- conductive film
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/103—Esters of polyhydric alcohols or polyhydric phenols of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
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Definitions
- the present invention relates to a protective film forming composition for a transparent conductive film.
- ITO indium tin oxide
- IZO indium zinc oxide
- these inorganic oxide films are complicated processes such as sputtering, high vacuum, and high temperature annealing are required. Therefore, there is a problem that special equipment is required and costs are high.
- the electrical resistance of the transparent conductive film having a conductive nanostructure can be lowered by simply increasing the amount of metal contained without requiring a complicated process.
- the increase in the amount of metal causes white turbidity due to irregular reflection of light, resulting in loss of optical transparency, and since it is a metal, there is a problem of loss of conductivity due to deterioration of the surface or destruction of the structure.
- This invention is made
- An object is to provide a composition.
- the present inventors have found that a composition containing a predetermined triazine ring-containing hyperbranched polymer and a crosslinking agent having a molecular weight of 1,000 or more has improved the visibility of the transparent conductive film.
- the present invention was completed by finding a film that can be improved and found that the film is suitable as a protective film for a transparent conductive film because of its high temperature and high humidity resistance.
- a protective film-forming composition for a transparent conductive film comprising a triazine ring-containing hyperbranched polymer containing a repeating unit structure represented by the following formula (1) and a crosslinking agent A having a molecular weight of 1,000 or more.
- R 1 to R 92 each independently represents a hydrogen atom, a halogen atom, a carboxyl group, a sulfone group, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms
- R 93 and R 94 represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
- W 1 and W 2 are each independently a single bond
- R 95 and R 96 are each independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.
- R 95 and R 96 are both alkyl groups, they may be bonded to each other to form a ring together with the carbon atom to which they are bonded.
- X 1 and X 2 each independently represent a single bond, an alkylene group having 1 to 10 carbon atoms or a group represented by the formula (14).
- R 98 to R 101 each independently represents a hydrogen atom, a halogen atom, a carboxyl group, a sulfone group, an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms, Y 1 and Y 2 each independently represents a single bond or an alkylene group having 1 to 10 carbon atoms.
- the crosslinking agent A is a polyfunctional (meth) acrylic compound.
- the composition according to 1 or 2 comprising 0.1 to 30 parts by mass of the crosslinking agent A with respect to 100 parts by mass of the triazine ring-containing hyperbranched polymer. 4).
- a protective film for a transparent conductive film obtained by curing any one of compositions 1 to 7.
- the protective film according to 8, wherein the transparent conductive film is a transparent conductive film having a conductive nanostructure. 10.
- Protective film of 9 whose conductive nanostructure is silver nanowire.
- An electronic device comprising a transparent conductive film and eight protective films formed on the transparent conductive film. 13 12 electronic devices that are organic electroluminescent displays.
- the protective film formed using the protective film-forming composition for transparent conductive film of the present invention has high transparency and a high refractive index, the visibility of the transparent conductive film can be improved, and further, heat resistance, Since the high temperature and high humidity resistance is also high, the deterioration of the transparent conductive film can be suppressed. That is, the protective film produced using the composition of the present invention can be suitably used as a protective film for a transparent conductive film.
- the protective film-forming composition for transparent conductive film of the present invention contains a triazine ring-containing hyperbranched polymer containing a repeating unit represented by the following formula (1).
- R and R ′ each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or an aralkyl group.
- the number of carbon atoms of the alkyl group is not particularly limited, but is preferably 1 to 20, more preferably 1 to 10 and even more preferably 1 to 3 in view of further improving the heat resistance of the polymer.
- the structure may be any of linear, branched and cyclic.
- alkyl group examples include methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, cyclobutyl group, 1-methyl group.
- -Cyclopropyl group 2-methyl-cyclopropyl group, n-pentyl group, 1-methyl-n-butyl group, 2-methyl-n-butyl group, 3-methyl-n-butyl group, 1,1-dimethyl -N-propyl group, 1,2-dimethyl-n-propyl group, 2,2-dimethyl-n-propyl group, 1-ethyl-n-propyl group, cyclopentyl group, 1-methyl-cyclobutyl group, 2-methyl -Cyclobutyl group, 3-methyl-cyclobutyl group, 1,2-dimethyl-cyclopropyl group, 2,3-dimethyl-cyclopropyl group, 1-ethyl-cyclopropyl group, 2-ethyl- Chloropropyl group, n-hexyl group, 1-methyl-n-pentyl group, 2-methyl-n-pentyl group, 3-methyl-n-pentyl group, 4-methyl-n-p
- the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20, more preferably 1 to 10 and even more preferably 1 to 3 in view of further improving the heat resistance of the polymer.
- the structure of the alkyl moiety may be any of linear, branched or cyclic.
- alkoxy group examples include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, s-butoxy group, t-butoxy group, n-pentyloxy group, 1-methyl -N-butoxy group, 2-methyl-n-butoxy group, 3-methyl-n-butoxy group, 1,1-dimethyl-n-propoxy group, 1,2-dimethyl-n-propoxy group, 2,2- Dimethyl-n-propoxy group, 1-ethyl-n-propoxy group, n-hexyloxy group, 1-methyl-n-pentyloxy group, 2-methyl-n-pentyloxy group, 3-methyl-n-pentyloxy 4-methyl-n-pentyloxy group, 1,1-dimethyl-n-butoxy group, 1,2-dimethyl-n-butoxy group, 1,3-dimethyl-n-butoxy group, 2,2-dimethyl group -N-butoxy group, 2,2-d
- the number of carbon atoms of the aryl group is not particularly limited, but is preferably 6 to 40, more preferably 6 to 16, and still more preferably 6 to 13 in view of further improving the heat resistance of the polymer.
- Specific examples of the aryl group include phenyl group, ⁇ -naphthyl group, ⁇ -naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group. 4-phenanthryl group, 9-phenanthryl group and the like.
- some or all of the hydrogen atoms of the aryl group are halogen atoms such as fluorine, chlorine, bromine, iodine, alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, nitro groups, cyano groups, It may be substituted with a phenyl group or the like.
- substituted aryl group examples include o-chlorophenyl group, m-chlorophenyl group, p-chlorophenyl group, o-fluorophenyl group, p-fluorophenyl group, o-methoxyphenyl group, p-methoxyphenyl group, p- Examples thereof include nitrophenyl group, p-cyanophenyl group, o-biphenylyl group, m-biphenylyl group, p-biphenylyl group and the like.
- the number of carbon atoms of the aralkyl group is not particularly limited, but is preferably 7 to 20, more preferably 7 to 17, and still more preferably 7 to 14.
- the alkylene moiety may be linear, branched or cyclic.
- Specific examples of the aralkyl group include a benzyl group, a phenethyl group, and a 1-naphthylmethyl group.
- the hydrogen atoms of the aralkyl group may be halogen atoms such as fluorine, chlorine, bromine, iodine, alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, nitro groups, cyano groups, It may be substituted with a phenyl group or the like.
- Specific examples of the substituted aralkyl group include p-methylphenylmethyl group, m-methylphenylmethyl group, o-ethylphenylmethyl group, m-ethylphenylmethyl group, p-ethylphenylmethyl group, 2-propylphenylmethyl group. 4-isopropylphenylmethyl group, 4-isobutylphenylmethyl group and the like.
- Ar represents at least one group selected from the group consisting of groups represented by formulas (2) to (13).
- R 1 to R 92 each independently represents a hydrogen atom, a halogen atom, a carboxyl group, a sulfone group, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms.
- R 93 and R 94 represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.
- W 1 and W 2 are each independently a single bond, —C (R 95 ) (R 96 ) — (R 95 and R 96 are each independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.
- R 95 and R 96 are both alkyl groups, they may be bonded to each other to form a ring together with the carbon atom to which they are bonded.), —C (O) —, —O—, —S —, —S (O) —, —S (O) 2 — or —N (R 97 ) — (R 97 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms).
- X 1 and X 2 each independently represent a single bond, an alkylene group having 1 to 10 carbon atoms or a group represented by the formula (14).
- R 98 to R 101 each independently represents a hydrogen atom, a halogen atom, a carboxyl group, a sulfone group, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms.
- Y 1 and Y 2 each independently represents a single bond or an alkylene group having 1 to 10 carbon atoms.
- Examples of the halogen atom represented by R 1 to R 101 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Further, examples of the alkyl group and alkoxy group represented by R 1 to R 101 include the same groups as those exemplified as R and R ′, and linear or branched ones are particularly preferable.
- alkylene group having 1 to 10 carbon atoms examples include groups in which one hydrogen atom has been removed from the alkyl groups exemplified as R and R ′, and in particular, linear or branched groups are preferred. Examples include a methylene group, an ethylene group, a propylene group, a trimethylene group, a tetramethylene group, and a pentamethylene group.
- Ar is preferably a group represented by the formulas (2), (5) to (13), and the formulas (2), (5), (7), (8), (11) to (13) Is more preferable.
- Specific examples of the groups represented by the formulas (2) to (13) include, but are not limited to, those represented by the following formulas.
- a group represented by the following formula is more preferable because a polymer having a higher refractive index can be obtained.
- the hyperbranched polymer used in the present invention preferably contains a repeating unit represented by the formula (15) particularly considering solubility in an organic solvent or the like.
- the weight average molecular weight (Mw) of the hyperbranched polymer used in the present invention is not particularly limited, but is preferably 500 to 500,000, and more preferably 1,000 to 100,000.
- the lower limit of Mw is preferably 2,000 from the viewpoint of further improving the heat resistance and lowering the shrinkage rate, and the upper limit thereof from the point of increasing the solubility and lowering the viscosity of the obtained solution. Is preferably 50,000, more preferably 30,000, and still more preferably 10,000.
- Mw is a standard polystyrene equivalent value determined by gel permeation chromatography (GPC) analysis.
- the triazine ring-containing hyperbranched polymer used in the present invention can be produced by the technique disclosed in Patent Document 4.
- the hyperbranched polymer (20) can be obtained by reacting a cyanuric halide (18) and an m-phenylenediamine compound (19) in a suitable organic solvent.
- R and R ′ are the same as above.
- X independently represents a halogen atom.
- the hyperbranched polymer (20) is a compound obtained by reacting cyanuric halide (18) and m-phenylenediamine compound (19) in an appropriate organic solvent using an equal amount ( 20 ').
- the amount of each raw material charged is arbitrary as long as the target polymer is obtained, but the diamine compound (19) 0.01 to 10 with respect to 1 equivalent of the triazine compound (18). Equivalents are preferred. However, in the case of the method of Scheme 1, it is preferable to avoid using 3 equivalents of the diamine compound (19) per 2 equivalents of cyanuric halide (18). By shifting the equivalent of the functional group, formation of a gelled product can be prevented.
- a hyperbranched polymer having many triazine ring ends with various molecular weights it is preferable to use the diamine compound (19) in an amount of less than 3 equivalents relative to 2 equivalents of cyanuric halide (18).
- a hyperbranched polymer having a large number of triazine ring ends is preferable in terms of having excellent transparency and light resistance.
- cyanuric halide (18) in an amount of less than 2 equivalents relative to 3 equivalents of diamine compound (19).
- the molecular weight of the resulting hyperbranched polymer can be easily adjusted by appropriately adjusting the amounts of the diamine compound (19) and the cyanuric halide (18).
- organic solvent various solvents usually used in this kind of reaction can be used, for example, tetrahydrofuran, dioxane, dimethyl sulfoxide; N, N-dimethylformamide, N-methyl-2-pyrrolidone, tetramethylurea.
- N, N-dimethylformamide, dimethyl sulfoxide, N-methyl-2-pyrrolidone, N, N-dimethylacetamide and mixed solvents thereof are preferred, and in particular, N, N-dimethylacetamide, N-methyl-2 -Pyrrolidone is preferred.
- the reaction temperature may be appropriately set in the range from the melting point to the boiling point of the solvent used, but is preferably about 0 to 150 ° C., more preferably 60 to 100 ° C. Particularly in the reaction of Scheme 1, the reaction temperature is preferably 60 to 150 ° C., preferably 80 to 150 ° C., and preferably 80 to 120 ° C. from the viewpoint of suppressing linearity and increasing the degree of branching.
- the reaction temperature may be appropriately set in the range from the melting point of the solvent used to the boiling point of the solvent, but is preferably about ⁇ 50 to 50 ° C., more preferably about ⁇ 20 to 50 ° C. Preferably, about ⁇ 10 to 50 ° C. is more preferable, and ⁇ 10 to 10 ° C. is still more preferable.
- it is preferable to employ a two-step process comprising a first step of reacting at ⁇ 50 to 50 ° C. and a second step of reacting at 60 to 150 ° C. following this step.
- the order of mixing the components is arbitrary, but in the reaction of Scheme 1, the solution containing cyanuric halide (18) or diamine compound (19) and an organic solvent is 60 to 150 ° C., preferably 80 ° C. A method of heating to ⁇ 150 ° C. and adding the diamine compound (19) or cyanuric halide (18) to the solution at this temperature is optimal.
- a component previously dissolved in a solvent or a component added later may be used, but a method of adding cyanuric halide (18) to a heated solution of the diamine compound (19) is preferable.
- a component previously dissolved in a solvent or a component added later may be used, but a method of adding a diamine compound (19) to a cooled solution of cyanuric halide (18) is preferable.
- Components added later may be added neat or in a solution dissolved in an organic solvent as described above, but the latter method is preferred in view of ease of operation and ease of reaction control. It is.
- components added later may be gradually added by dropping or the like, or may be added all at once.
- various bases usually used during polymerization or after polymerization may be added.
- this base include potassium carbonate, potassium hydroxide, sodium carbonate, sodium hydroxide, sodium hydrogen carbonate, sodium ethoxide, sodium acetate, lithium carbonate, lithium hydroxide, lithium oxide, potassium acetate, magnesium oxide, oxidized Calcium, barium hydroxide, trilithium phosphate, trisodium phosphate, tripotassium phosphate, cesium fluoride, aluminum oxide, ammonia, trimethylamine, triethylamine, diisopropylamine, diisopropylethylamine, N-methylpiperidine, 2,2,6 , 6-tetramethyl-N-methylpiperidine, pyridine, 4-dimethylaminopyridine, N-methylmorpholine and the like.
- the amount of the base added is preferably 1 to 100 equivalents, more preferably 1 to 10 equivalents per equivalent of cyanuric halide (18). These bases may be used as an aqueous solution.
- the product can be easily purified by a reprecipitation method or the like after completion of the reaction.
- At least one of the halogen atoms of the terminal triazine ring is substituted with an alkyl group, an aralkyl group, an aryl group, an alkylamino group, an alkoxysilyl group-containing alkylamino group, an aralkylamino group, an arylamino group, You may cap by an alkoxy group, an aralkyloxy group, an aryloxy group, an ester group, etc.
- an alkylamino group, an alkoxysilyl group-containing alkylamino group, an aralkylamino group, and an arylamino group are preferable, an alkylamino group and an arylamino group are more preferable, and an arylamino group is still more preferable.
- alkyl group examples include alkoxy group, aryl group and aralkyl group.
- ester group examples include a methoxycarbonyl group and an ethoxycarbonyl group.
- alkylamino group examples include methylamino group, ethylamino group, n-propylamino group, isopropylamino group, n-butylamino group, isobutylamino group, s-butylamino group, t-butylamino group, n -Pentylamino group, 1-methyl-n-butylamino group, 2-methyl-n-butylamino group, 3-methyl-n-butylamino group, 1,1-dimethyl-n-propylamino group, 1,2 -Dimethyl-n-propylamino group, 2,2-dimethyl-n-propylamino group, 1-ethyl-n-propylamino group, n-hexylamino group, 1-methyl-n-pentylamino group, 2-methyl -N-pentylamino group, 3-methyl-n-pentylamino group, 4-methyl-n-pentyl
- aralkylamino group examples include benzylamino group, methoxycarbonylphenylmethylamino group, ethoxycarbonylphenylmethylamino group, p-methylphenylmethylamino group, m-methylphenylmethylamino group, and o-ethylphenylmethylamino group.
- arylamino group examples include phenylamino group, methoxycarbonylphenylamino group, ethoxycarbonylphenylamino group, naphthylamino group, methoxycarbonylnaphthylamino group, ethoxycarbonylnaphthylamino group, anthranylamino group, pyrenylamino group, biphenylamino. Group, terphenylamino group, fluorenylamino group and the like.
- the alkoxysilyl group-containing alkylamino group may be a monoalkoxysilyl group-containing alkylamino group, a dialkoxysilyl group-containing alkylamino group, or a trialkoxysilyl group-containing alkylamino group.
- Specific examples thereof include 3-trimethoxy Silylpropylamino group, 3-triethoxysilylpropylamino group, 3-dimethylethoxysilylpropylamino group, 3-methyldiethoxysilylpropylamino group, N- (2-aminoethyl) -3-dimethylmethoxysilylpropylamino group N- (2-aminoethyl) -3-methyldimethoxysilylpropylamino group, N- (2-aminoethyl) -3-trimethoxysilylpropylamino group, and the like.
- aryloxy group examples include phenoxy group, naphthoxy group, anthranyloxy group, pyrenyloxy group, biphenyloxy group, terphenyloxy group, fluorenyloxy group and the like.
- aralkyloxy group examples include benzyloxy group, p-methylphenylmethyloxy group, m-methylphenylmethyloxy group, o-ethylphenylmethyloxy group, m-ethylphenylmethyloxy group, p-ethylphenylmethyl group.
- examples include an oxy group, 2-propylphenylmethyloxy group, 4-isopropylphenylmethyloxy group, 4-isobutylphenylmethyloxy group, ⁇ -naphthylmethyloxy group, and the like.
- the organic monoamine is charged simultaneously. That is, by reacting a cyanuric halide compound and a diaminoaryl compound in the presence of an organic monoamine, it is possible to obtain a soft hyperbranched polymer having a low degree of branching in which the rigidity of the hyperbranched polymer is relaxed.
- the hyperbranched polymer obtained by this technique has excellent solubility in a solvent (inhibition of aggregation) and crosslinkability with a crosslinking agent, and thus is particularly advantageous when used as a composition in combination with a crosslinking agent described later. It is.
- any of alkyl monoamine, aralkyl monoamine, and aryl monoamine can be used.
- Alkyl monoamines include methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, s-butylamine, t-butylamine, n-pentylamine, 1-methyl-n-butylamine, 2-methyl- n-butylamine, 3-methyl-n-butylamine, 1,1-dimethyl-n-propylamine, 1,2-dimethyl-n-propylamine, 2,2-dimethyl-n-propylamine, 1-ethyl-n -Propylamine, n-hexylamine, 1-methyl-n-pentylamine, 2-methyl-n-pentylamine, 3-methyl-n-pentylamine, 4-methyl-n-pentylamine, 1,1-dimethyl -N-butylamine, 1,2-dimethyl-n-butylamine, 1,3-dimethyl-n-butyl 2,2-
- aralkyl monoamine examples include benzylamine, p-methoxycarbonylbenzylamine, p-ethoxycarbonylphenylbenzyl, p-methylbenzylamine, m-methylbenzylamine, o-methoxybenzylamine and the like.
- aryl monoamine examples include aniline, p-methoxycarbonylaniline, p-ethoxycarbonylaniline, p-methoxyaniline, 1-naphthylamine, 2-naphthylamine, anthranylamine, 1-aminopyrene, 4-biphenylylamine, o- And phenylaniline, 4-amino-p-terphenyl, 2-aminofluorene, and the like.
- the amount of the organic monoamine used is preferably 0.05 to 500 equivalents, more preferably 0.05 to 120 equivalents, and even more preferably 0.05 to 50 equivalents based on the halogenated cyanuric compound. .
- the reaction temperature is preferably 60 to 150 ° C., more preferably 80 to 150 ° C., and preferably 80 to 120 ° C. from the viewpoint of suppressing linearity and increasing the degree of branching.
- the mixing of the three components of the organic monoamine, the halogenated cyanuric compound and the diaminoaryl compound may be performed at a low temperature.
- the temperature is preferably about ⁇ 50 to 50 ° C., and about ⁇ 20 to 50 ° C. Is more preferable, and ⁇ 20 to 10 ° C. is more preferable.
- After the low temperature charging it is preferable to carry out the reaction by raising the temperature to the polymerization temperature at once (in one step).
- the two components of the cyanuric halide compound and the diaminoaryl compound may be mixed at a low temperature.
- the temperature is preferably about ⁇ 50 to 50 ° C., more preferably about ⁇ 20 to 50 ° C., More preferably, it is ⁇ 20 to 10 ° C. It is preferable to carry out the reaction by adding an organic monoamine after the low-temperature charging and raising the temperature to a temperature for polymerization (in one step).
- the composition of the present invention contains a crosslinking agent A having a molecular weight of 1,000 or more. Thereby, the film density of the protective film can be increased and the high temperature and high humidity resistance can be improved.
- the composition of the present invention preferably further contains a crosslinking agent B having a molecular weight of less than 1,000.
- a crosslinking agent B having a molecular weight of less than 1,000.
- the crosslinking agent B preferably has a molecular weight of 900 or less, and more preferably 800 or less.
- crosslinking agents A and B a compound containing a crosslinking group such as a melamine compound, a substituted urea compound, an epoxy group or an oxetane group having a crosslinking group such as a methylol group or a methoxymethyl group as a crosslinking group, a block Examples thereof include a compound containing an isocyanate, a compound having an acid anhydride, a compound having a (meth) acryloyl group, an aminoplast compound, and a phenoplast compound.
- a compound containing an epoxy group, a blocked isocyanate group, or a (meth) acryl group is preferable, and in particular, a compound having a blocked isocyanate group or an initiator is used.
- Polyfunctional epoxy compounds and / or polyfunctional (meth) acrylic compounds that give a photocurable composition at least are preferred.
- polyfunctional compounds need to have at least 2 crosslink forming groups, it is preferable to have 3 or more crosslink forming groups.
- the polyfunctional epoxy compound is not particularly limited as long as it has two or more epoxy groups in one molecule. Specific examples thereof include tris (2,3-epoxypropyl) isocyanurate, 1,4-butanediol diglycidyl ether, 1,2-epoxy-4- (epoxyethyl) cyclohexane, glycerol triglycidyl ether, diethylene glycol diglycidyl.
- epoxy resins having at least two epoxy groups YH-434, YH-434L (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.); Epolide GT-401, which is an epoxy resin having a cyclohexene oxide structure , GT-403, GT-301, GT-302, Celoxide 2021, 3000 (manufactured by Daicel Corporation); bisphenol A type epoxy resin, jER (registered trademark) 1001, 1002, 1003, 1004, 1007, 1009, 1010, 828 (Mitsubishi Chemical Corporation); bisphenol F type epoxy resin, jER (registered trademark) 807 (Mitsubishi Chemical Corporation); phenol novolac type epoxy resin, jER (registered trademark) 152, 154 (Mitsubishi Chemical Corporation), EPPN 201, 202 (hereinafter EOCN-102, EOCN-103S, EOCN-104S, EOCN-1020, EOCN-1025, EOCN
- the polyfunctional (meth) acrylic compound is not particularly limited as long as it has two or more (meth) acrylic groups in one molecule. Specific examples thereof include ethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, ethoxylated bisphenol A di (meth) acrylate, ethoxylated trimethylolpropane tri (meth) acrylate, and ethoxylated glycerin tri (meth).
- polyfunctional (meth) acrylic compounds are available as commercial products, and specific examples thereof include NK esters A-200, A-400, A-600, A-1000, A-9300, A-9300. -1CL, A-TMPT, A-TMM-3, A-TMM-3L, A-TMP, A-TMMT, A-DPH, UA-53H, 1G, 2G, 3G, 4G, 9G, 14G, 23G, ABE -300, A-BPE-4, A-BPE-6, A-BPE-10, A-BPE-20, A-BPE-30, BPE-80N, BPE-100N, BPE-200, BPE-500, BPE -900, BPE-1300N, A-GLY-3E, A-GLY-9E, A-GLY-20E, A-TMPT-3EO, A-TMPT-9EO, ATM-4E, ATM-35E, A -20E (manufactured by Shin-Nakamura Chemical Co., Ltd.), KAYA
- EBECRYL registered trademark
- the acid anhydride compound is not particularly limited as long as it is a carboxylic acid anhydride obtained by dehydration condensation of two molecules of carboxylic acid.
- Specific examples thereof include phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, nadic anhydride, methyl nadic anhydride, maleic anhydride, succinic anhydride, Those having one acid anhydride group in the molecule such as octyl succinic anhydride and dodecenyl succinic anhydride; 1,2,3,4-cyclobutanetetracarboxylic dianhydride, pyromellitic anhydride, 3,4 -Dicarboxy-1,2,3,4-tetrahydro-1-naphthalene succinic dianhydride, bicyclo [3.3.0] octane
- a compound containing a blocked isocyanate has two or more blocked isocyanate groups in which one or more isocyanate groups (—NCO) are blocked by an appropriate protective group, and when exposed to a high temperature during thermal curing, There is no particular limitation as long as the protecting group (block portion) is dissociated by thermal dissociation, and the resulting isocyanate group causes a crosslinking reaction with the resin.
- the protecting group (block portion) is dissociated by thermal dissociation, and the resulting isocyanate group causes a crosslinking reaction with the resin.
- two groups represented by the following formula are included in one molecule. Examples thereof include compounds having the above-mentioned (these groups may be the same or different from each other).
- R b represents an organic group in the block part.
- Such a compound can be obtained, for example, by reacting an appropriate blocking agent with a compound having two or more isocyanate groups in one molecule.
- Examples of the compound having two or more isocyanate groups in one molecule include polyisocyanates such as isophorone diisocyanate, 1,6-hexamethylene diisocyanate, methylene bis (4-cyclohexyl isocyanate), trimethylhexamethylene diisocyanate, and dimers thereof. And trimers, and reaction products of these with diols, triols, diamines, or triamines.
- the blocking agent examples include alcohols such as methanol, ethanol, isopropanol, n-butanol, 2-ethoxyhexanol, 2-N, N-dimethylaminoethanol, 2-ethoxyethanol, cyclohexanol; phenol, o-nitrophenol Phenols such as p-chlorophenol, o-, m- or p-cresol; lactams such as ⁇ -caprolactam; oximes such as acetone oxime, methyl ethyl ketone oxime, methyl isobutyl ketone oxime, cyclohexanone oxime, acetophenone oxime, and benzophenone oxime And pyrazoles such as pyrazole, 3,5-dimethylpyrazole and 3-methylpyrazole; thiols such as dodecanethiol and benzenethiol.
- alcohols such as methanol, ethanol, isoprop
- a compound containing a blocked isocyanate is also available as a commercial product.
- Specific examples thereof include B-830, B-815N, B-842N, B-870N, B-874N, B-882N, B- 7005, B-7030, B-7075, B-5010 (Mitsui Chemicals), Duranate (registered trademark) 17B-60PX, TPA-B80E, MF-B60X, MF-K60X, E402-B80T (Asahi Kasei Chemicals ( Co., Ltd.), Karenz MOI-BM (registered trademark) (manufactured by Showa Denko KK) and the like.
- the aminoplast compound is not particularly limited as long as it has two or more methoxymethylene groups in one molecule.
- CYMEL registered trademark
- 303 hexamethoxymethylmelamine
- 1170 tetrabutoxymethylglycoluril
- 1123 tetramethoxymethylbenzoguanamine
- Nicalak which is a methylated melamine resin (Registered trademark) MW-30HM, MW-390, MW-100LM, MX-750LM, Nika such as MX-270, MX-280, MX-290 (manufactured by Sanwa Chemical Co., Ltd.) which are methylated urea resins
- Examples include melamine compounds such as the rack series.
- the oxetane compound is not particularly limited as long as it has two or more oxetanyl groups in one molecule.
- OXT-221, OX-SQ-H, OX-SC containing oxetane group manufactured by Toagosei Co., Ltd.) ) And the like.
- the phenoplast compound has two or more hydroxymethylene groups in one molecule, and when exposed to a high temperature during thermosetting, the crosslinking reaction proceeds with the hyperbranched polymer used in the present invention by a dehydration condensation reaction.
- the phenoplast compound include 2,6-dihydroxymethyl-4-methylphenol, 2,4-dihydroxymethyl-6-methylphenol, bis (2-hydroxy-3-hydroxymethyl-5-methylphenyl) methane, Bis (4-hydroxy-3-hydroxymethyl-5-methylphenyl) methane, 2,2-bis (4-hydroxy-3,5-dihydroxymethylphenyl) propane, bis (3-formyl-4-hydroxyphenyl) methane Bis (4-hydroxy-2,5-dimethylphenyl) formylmethane, ⁇ , ⁇ -bis (4-hydroxy-2,5-dimethylphenyl) -4-formyltoluene and the like.
- the phenoplast compound is also available as a commercial product. Specific examples thereof include 26DMPC, 46DMOC, DM-BIPC-F, DM-BIOC-F, TM-BIP-A, BISA-F, BI25X-DF, BI25X-TPA (Asahi Organic Materials Co., Ltd.) etc. are mentioned.
- the cross-linking agent A preferably has a molecular weight of 1,000 or more due to a long chain length between cross-linking groups, and specifically has a polyether structure, a polyester structure, a polyurethane structure, etc. Thus, those in which the chain length between the cross-linking groups is long are preferred.
- the crosslinking agent A includes NK ester A-GLY-20E, ATM-35E, AT-20E, 23G, A-BPE-20BPE-900, BPE-1300N (Shin Nakamura Chemical Co., Ltd.) Manufactured), EBECRYL (registered trademark) 204, 205, 210, 215, 230, 244, 245, 270, 284, 285, 264, 265, 294 / 25HD, 1259, 1290, 4820, 8254, 8301R, 8405, 8465, 8296, 8307, 8411, 8701, 8800, 8804, 9260, 9277EA, KRM8200, 8452, 8528, 8667, 8904, 436, 438, 446, 450, 525, 1830, 846, 1870, 884, 885, 860, 3708 ( Ornex)), UV- 700B, UV-6300B, UV
- the crosslinking agent B having a molecular weight of less than 1,000 includes Aronix (registered trademark) M-303, M-305, M-305, M-306, M-400, M-402, M-403, M-404, M-405, M-406, M-450, M-452 (manufactured by Toagosei Co., Ltd.), NK ester A-9300, A-9300-1CL, A-TMM-3, A-TMM-3L, A-TMPT, A-TMP, A-TMMT, A-DPH, 1G, 2G, 3G, 4G, 9G, 14G, ABE-300, A-BPE-4, A-BPE-6, A-BPE-10, A-BPE-20, A-BPE-30, BPE-80N, BPE-100N, BPE-200, BPE-500 (manufactured by Shin-Nakamura Chemical Co., Ltd.), EBECRYL (registered trademark) 11 , 40,
- Aronix registered trademark
- M-303, M-305, M-305, M-306, M-400, M-402, M-403, M-404, M-405, M-406, M -450, M-452 manufactured by Toagosei Co., Ltd.
- NK ester A-9300, A-9300-1CL manufactured by Shin-Nakamura Chemical Co., Ltd.
- NK ester A-9300, A-9300-1CL manufactured by Shin-Nakamura Chemical Co., Ltd.
- crosslinking agents A and B polyfunctional (meth) acrylic compounds are suitable from the viewpoint that the refractive index lowering due to the crosslinking agent blending can be suppressed and the curing reaction proceeds promptly.
- Crosslinking agents A and B may be used alone or in combination of two or more.
- the amount of the crosslinking agent A used is preferably 0.1 to 30 parts by mass with respect to 100 parts by mass of the triazine ring-containing hyperbranched polymer, but considering the solvent resistance, the lower limit is preferably 1 part by mass, more preferably In consideration of controlling the refractive index, the upper limit is preferably 25 parts by mass, more preferably 20 parts by mass.
- the amount of the crosslinking agent B used is preferably 0.5 to 400 parts by mass, more preferably 50 to 200 parts by mass with respect to 100 parts by mass of the crosslinking agent A. If the amount is less than 0.5 parts by mass, the protective effect of the transparent conductive film may not be improved. If the amount exceeds 400 parts by mass, the refractive index may be significantly lowered.
- solvent in the composition of the present invention, it is preferable to use various solvents by dissolving the triazine ring-containing hyperbranched polymer.
- the solvent may be the same as or different from the solvent used during the polymerization. This solvent is not particularly limited as long as the compatibility with the polymer is not impaired.
- usable solvents include toluene, p-xylene, o-xylene, m-xylene, ethylbenzene, styrene, ethylene glycol dimethyl ether, propylene glycol monomethyl ether, ethylene glycol monomethyl ether, propylene glycol, propylene glycol monoethyl ether.
- Ethylene glycol monoethyl ether ethylene glycol monoisopropyl ether, ethylene glycol methyl ether acetate, propylene glycol monomethyl ether acetate, ethylene glycol ethyl ether acetate, diethylene glycol dimethyl ether, propylene glycol monobutyl ether, ethylene glycol monobutyl ether, diethylene glycol diethyl ether, dip Pyrene glycol monomethyl ether, diethylene glycol monomethyl ether, dipropylene glycol monoethyl ether, diethylene glycol monoethyl ether, triethylene glycol dimethyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol, 1-octanol, ethylene glycol, hexylene glycol, trimethylene glycol, 1 -Methoxy-2-butanol, cyclohexanol, diacetone alcohol, furfuryl alcohol, tetrahydrofurfury
- the solid content concentration in the composition is not particularly limited as long as it does not affect the storage stability, and may be appropriately set according to the target film thickness.
- the solid content concentration is preferably 0.1 to 50% by mass, and more preferably 0.2 to 40% by mass.
- an initiator corresponding to each crosslinking agent can be blended.
- a polyfunctional epoxy compound and / or a polyfunctional (meth) acrylic compound is used as a crosslinking agent, photocuring proceeds without using an initiator to give a cured film.
- an initiator may be used.
- a photoacid generator or a photobase generator can be used.
- the photoacid generator may be appropriately selected from known ones, and for example, onium salt derivatives such as diazonium salts, sulfonium salts, iodonium salts can be used. Specific examples thereof include phenyldiazonium hexafluorophosphate, aryldiazonium salts such as 4-methoxyphenyldiazonium hexafluoroantimonate, 4-methylphenyldiazonium hexafluorophosphate; diphenyliodonium hexafluoroantimonate, di (4-methylphenyl) Diaryliodonium salts such as iodonium hexafluorophosphate, di (4-tert-butylphenyl) iodonium hexafluorophosphate; triphenylsulfonium hexafluoroantimonate, tris (4-methoxyphenyl) sulfonium hexafluorophosphat
- onium salts commercially available products may be used. Specific examples thereof include Sun-Aid SI-60, SI-80, SI-100, SI-60L, SI-80L, SI-100L, SI-L145, SI- L150, SI-L160, SI-L110, SI-L147 (manufactured by Sanshin Chemical Industry Co., Ltd.), UVI-6950, UVI-6970, UVI-6974, UVI-6990, UVI-6990 (manufactured by Union Carbide), CPI-100P, CPI-100A, CPI-200K, CPI-200S (manufactured by San Apro), Adeka optomer SP-150, SP-151, SP-170, SP-171 (manufactured by ADEKA), Irgacure (Registered trademark) 261 (manufactured by BASF), CI-2481, CI-2624, CI-2639, CI- 064 (manufactured by Nippon Soda Co
- the photobase generator may be appropriately selected from known ones.
- a Co-amine complex, oxime carboxylic acid ester, carbamic acid ester, or quaternary ammonium salt photobase generator may be used. it can.
- Specific examples include 2-nitrobenzylcyclohexyl carbamate, triphenylmethanol, O-carbamoylhydroxylamide, O-carbamoyloxime, [[(2,6-dinitrobenzyl) oxy] carbonyl] cyclohexylamine, bis [[(2 -Nitrobenzyl) oxy] carbonyl] hexane 1,6-diamine, 4- (methylthiobenzoyl) -1-methyl-1-morpholinoethane, (4-morpholinobenzoyl) -1-benzyl-1-dimethylaminopropane, N- (2-nitrobenzyloxycarbonyl) pyrrolidine, hexaamminecobalt (III) tris (triphen
- a photoacid generator or a photobase generator When a photoacid generator or a photobase generator is used, it is preferably used in the range of 0.1 to 15 parts by mass, more preferably in the range of 1 to 10 parts by mass with respect to 100 parts by mass of the polyfunctional epoxy compound. It is.
- a photo radical polymerization initiator when a polyfunctional (meth) acrylic compound is used, a photo radical polymerization initiator can be used.
- the radical photopolymerization initiator may be appropriately selected from known ones, and examples thereof include acetophenones, benzophenones, Michler's benzoylbenzoate, amyloxime ester, tetramethylthiuram monosulfide, and thioxanthones.
- a photocleavable photo radical polymerization initiator is preferred.
- the photocleavable photoradical polymerization initiator is described in the latest UV curing technology (p. 159, publisher: Kazuhiro Takasawa, publisher: Technical Information Association, published in 1991).
- photo radical polymerization initiators examples include Irgacure (registered trademark) 127, 184, 369, 379, 651, 500, 819, 907, 784, 2959, OXE01, OXE02, CGI1700, CGI1750, CGI1850, CG24-61.
- radical photopolymerization initiator When a radical photopolymerization initiator is used, it is preferably used in the range of 0.1 to 15 parts by mass, more preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the polyfunctional (meth) acrylate compound. It is a range.
- the film-forming composition of the present invention may contain other components such as a leveling agent and a surfactant as long as the effects of the present invention are not impaired.
- leveling agent or surfactant examples include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene octylphenol ether, polyoxyethylene octylphenol ether, Polyoxyethylene alkyl allyl ethers such as oxyethylene nonylphenol ether, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan Sorbitan fatty acid esters such as tristearate, polyoxyethylene sorbitan monolaurate, poly Nonionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as oxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan
- the amount of the surfactant used is preferably from 0.0001 to 5 parts by weight, more preferably from 0.001 to 1 part by weight, and from 0.01 to 0.5 parts by weight based on 100 parts by weight of the triazine ring-containing hyperbranched polymer. Is even more preferable.
- the said other component can be added at the arbitrary processes at the time of preparing the composition of this invention.
- the protective film for transparent conductive film of the present invention is obtained by applying the protective film forming composition for transparent conductive film described above to the transparent conductive film, heating it as necessary to evaporate the solvent, and then heating or irradiating with light. Can be formed.
- Film density of the protective film is preferably 1.20 ⁇ 1.45g / cm 3, more preferably 1.30 ⁇ 1.45g / cm 3. When the film density is less than 1.20 g / cm 3 , the rate of change in resistance value may increase.
- the lower limit of the refractive index range of the protective film of the present invention is preferably 1.60, more preferably 1.65, and even more preferably 1.70.
- the upper limit is not particularly limited, but is about 1.95 to 2.00.
- the film thickness of the protective film of the present invention is preferably 10 to 1,000 nm, more preferably 50 to 200 nm.
- the haze value of the transparent conductive film on which the protective film of the present invention is formed is preferably 1.5% or less, more preferably 1.0% or less.
- the coating method of the composition is arbitrary, for example, spin coating method, dip method, flow coating method, ink jet method, spray method, bar coating method, gravure coating method, slit coating method, roll coating method, transfer printing method, brush Methods such as coating, blade coating, and air knife coating can be employed.
- a transparent conductive film having a conductive nanostructure such as an ITO film, an IZO film, a metal nanoparticle, a metal nanowire, or a metal nanomesh is preferable, and a transparent conductive film having a conductive nanostructure is more preferable.
- the metal which comprises electroconductive nanostructure is not specifically limited, Silver, gold
- a transparent conductive film having silver nanoparticles, silver nanowires, silver nanomesh, gold nanoparticles, gold nanowires, gold nanomesh, copper nanoparticles, copper nanowires, copper nanomesh, etc. is preferred, and transparent conductive materials having silver nanowires in particular.
- a membrane is preferred.
- the firing temperature is not particularly limited for the purpose of evaporating the solvent, and can be carried out at 40 to 400 ° C., for example.
- the baking method is not particularly limited.
- the solvent may be evaporated using a hot plate or an oven in an appropriate atmosphere such as air, an inert gas such as nitrogen, or in a vacuum.
- the firing temperature and firing time may be selected in accordance with the process steps of the target electronic device, and the firing conditions may be selected so that the physical properties of the obtained film meet the required characteristics of the electronic device.
- Conditions for light irradiation are not particularly limited, and an appropriate irradiation energy and time may be employed depending on the triazine ring-containing hyperbranched polymer and the crosslinking agent to be used. For example, it can be performed at 50 to 1,000 mJ / cm 2 . Moreover, it is preferable that light irradiation is performed in air
- the protective film of the present invention is particularly suitable as a protective film for a transparent conductive film having a conductive nanostructure.
- a transparent conductive film having a conductive nanostructure is likely to be clouded due to irregular reflection of light due to the conductive nanostructure, and may have poor visibility.
- the protective film of the present invention has high transparency and a high refractive index, visibility can be improved by preventing white turbidity caused by light irregular reflection of a transparent conductive film using a conductive nanostructure. Furthermore, since it has high heat resistance and high temperature and high humidity resistance, it can also contribute to prevention of deterioration of the transparent conductive film. Therefore, the protective film of this invention is suitable as a member for transparent electrodes.
- a liquid crystal display an organic electroluminescence (EL) display, a touch panel, an optical semiconductor (LED) element, a solid-state imaging element, an organic thin film solar cell, a dye-sensitized solar cell, It can be suitably used as a member for producing an electronic device such as an organic thin film transistor (TFT).
- TFT organic thin film transistor
- TG-DTA Different thermal balance
- Equipment TG-8120 manufactured by Rigaku Corporation Temperature increase rate: 10 ° C / min Measurement temperature: 25-750 ° C
- Equipment Light spec constant temperature (humidity) LHU-113 manufactured by ESPEC Corporation
- HZE Equipment: Nippon Denshoku Industries Co., Ltd.
- Optical microscope Equipment: Research microscope BX51 manufactured by OLYMPUS Co., Ltd.
- Non-contact type sheet resistance measuring instrument Equipment: Napson Corporation EC-80 [Film density measurement]
- Device Bruker AXS Multifunctional Thin Film Material Evaluation X-ray Diffractometer D8 DISCOVER
- DMAc dimethylacetamide
- reaction solution was stirred for 30 minutes, and this reaction solution was added dropwise to a tank heated in advance to 85 ° C. with an oil bath at a temperature of 85 ° C. in a 2,000 mL four-necked flask over a period of 1 hour and stirred for 1 hour. And polymerized.
- aniline 113.95 g, 1.224 mol
- triethylamine 116.36 g, 1.15 mol
- the precipitate was filtered, dried at 150 ° C.
- HB-TmDA40 hyperbranched polymer [3]
- HB-TmDA40 had an Mw of 4,300 and a dispersity of 3.44.
- HB-TmDA40V1 100 g of HB-TmDA40 obtained in Synthesis Example 1 was dissolved in a mixed solvent of 384.0 g of cyclohexanone and 16.0 g of ion-exchanged water to prepare a 20% by mass solution (hereinafter referred to as HB-TmDA40V1).
- Preparation Example 3 Production of Transparent Conductive Film After the conductive ink A prepared in Preparation Example 2 was formed on an alkali-free glass substrate by spin coating at 200 rpm for 5 seconds, then 900 rpm for 30 seconds, a hot plate It dried at 120 degreeC for 1 minute above, and produced the transparent conductive film.
- Example 4 to 6 Measurement of refractive index
- Each varnish prepared in Examples 1 to 3 was spin-coated on a soda lime silica glass substrate at 200 rpm for 5 seconds and at 1,000 rpm for 30 seconds using an spin coater. Was baked at 130 ° C. for 3 minutes. Thereafter, using a high-pressure mercury lamp, the film was cured at an integrated exposure amount of 400 mJ / cm 2 in the atmosphere (Examples 4 and 6) or in a nitrogen atmosphere (Example 5) to obtain a cured film having a thickness of 100 nm. Table 1 shows the measurement results of the refractive index of the obtained film.
- Example 7 to 9 Measurement of film density
- Each varnish prepared in Examples 1 to 3 was spin-coated on a silicon wafer substrate using a spin coater for 5 seconds at 200 rpm and 30 seconds at 1,000 rpm, and then using an oven. Then, baking was performed at 130 ° C. for 3 minutes. Then, using a high pressure mercury lamp, under air or under a nitrogen atmosphere and cured in integrated exposure amount 400 mJ / cm 2, to obtain a cured film having a thickness of 100 nm. These cured films were subjected to XRR measurement, and the film density was calculated. Table 2 shows the measurement results of the varnish, exposure environment, and film density used in each example.
- each varnish prepared in Examples 1 to 3 was made to have a solid content of 2%.
- the sample was diluted with cyclohexanone, spin-coated at 200 rpm for 5 seconds and 1,000 rpm for 30 seconds using a spin coater, and baked at 130 ° C. for 3 minutes using an oven. Thereafter, using a high-pressure mercury lamp, the film was cured at an integrated exposure of 400 mJ / cm 2 in the air or in a nitrogen atmosphere to form a protective film with a film thickness of 50 nm, and the haze value was measured (Examples 10 to 14). ).
- the decrease in the conductivity of the transparent conductive film greatly affects the device performance. It has been found that the protective film of the present invention has the effect of improving the visibility of the transparent conductive film and suppressing the deterioration of the transparent conductive film. In particular, in Example 12, it was found that the rate of change in resistance value was also small.
- Example 16 Measurement of refractive index of coating film HB-TmDA40VPF1 prepared in Example 15 was spin-coated on a soda lime glass substrate at 200 rpm for 5 seconds at 1,500 rpm for 30 seconds, using an oven. Then, baking was performed at 120 ° C. for 3 minutes. Thereafter, using a high-pressure mercury lamp, curing was performed under nitrogen at an integrated exposure amount of 400 mJ / cm 2 to obtain a cured film having a thickness of 57 nm. The refractive index of the obtained film was 1.5683 (wavelength 550 nm).
- Example 17 On the transparent conductive film prepared in Preparation Example 3, HB-TmDA40VPF1 prepared in Example 15 was spin-coated at 200 rpm for 5 seconds and 1500 rpm for 30 seconds using a spin coater, and at 120 ° C. using an oven. Firing was performed for 3 minutes. Then, using a high pressure mercury lamp, it hardened
- Example 18 The sample obtained in Example 17 was placed in a constant temperature and humidity tester set to 85 ° C. and 85% relative humidity, and the sheet resistance change after being held for 168 to 500 hours was measured. The results are shown in Table 5. In Table 5, 0h indicates the sheet resistance immediately after the preparation of the sample.
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Abstract
Description
1.下記式(1)で表される繰り返し単位構造を含むトリアジン環含有ハイパーブランチポリマー及び分子量1,000以上の架橋剤Aを含有することを特徴とする透明導電膜用保護膜形成組成物。
Arは、式(2)~(13)で示される基からなる群から選ばれる少なくとも1種の基を表す。
R93及びR94は、水素原子又は炭素数1~10のアルキル基を表し、
W1及びW2は、それぞれ独立に、単結合、-C(R95)(R96)-(R95及びR96は、それぞれ独立に、水素原子又は炭素数1~10のアルキル基を表し、R95及びR96がともにアルキル基である場合、これらは互いに結合してこれらが結合する炭素原子とともに環を形成してもよい。)、-C(O)-、-O-、-S-、-S(O)-、-S(O)2-又は-N(R97)-(R97は、水素原子又は炭素数1~10のアルキル基を表す。)を表し、
X1及びX2は、それぞれ独立に、単結合、炭素数1~10のアルキレン基又は式(14)で表される基を表す。
Y1及びY2は、それぞれ独立に、単結合又は炭素数1~10のアルキレン基を表す。)]}
2.架橋剤Aが多官能(メタ)アクリル化合物である1の組成物。
3.架橋剤Aを前記トリアジン環含有ハイパーブランチポリマー100質量部に対して0.1~30質量部含む1又は2の組成物。
4.更に、分子量1,000未満の架橋剤Bを含有する1~3のいずれかの組成物。
5.架橋剤Bが、多官能(メタ)アクリル化合物である4の組成物。
6.架橋剤Bを架橋剤A100質量部に対して0.5~400質量部含む4又は5の組成物。
7.更に溶媒を含む1~6のいずれかの組成物。
8.1~7のいずれかの組成物を硬化させて得られる透明導電膜用保護膜。
9.透明導電膜が導電性ナノ構造を有する透明導電膜である8の保護膜。
10.導電性ナノ構造が銀ナノワイヤである9の保護膜。
11.透明導電膜と該透明導電膜上に形成された8の保護膜とを備える透明電極。
12.透明導電膜と該透明導電膜上に形成された8の保護膜とを備える電子デバイス。
13.有機エレクトロルミネッセンスディスプレイである12の電子デバイス。
本発明の透明導電膜用保護膜形成組成物は、下記式(1)で表される繰り返し単位を含むトリアジン環含有ハイパーブランチポリマーを含有する。
R93及びR94は、水素原子又は炭素数1~10のアルキル基を表す。
W1及びW2は、それぞれ独立に、単結合、-C(R95)(R96)-(R95及びR96は、それぞれ独立に、水素原子又は炭素数1~10のアルキル基を表し、R95及びR96がともにアルキル基である場合、これらは互いに結合してこれらが結合する炭素原子とともに環を形成してもよい。)、-C(O)-、-O-、-S-、-S(O)-、-S(O)2-又は-N(R97)-(R97は、水素原子又は炭素数1~10のアルキル基を表す。)を表す。
本発明で用いるトリアジン環含有ハイパーブランチポリマーは、特許文献4に開示された手法によって製造することができる。
例えば、下記スキーム1に示されるように、ハイパーブランチポリマー(20)は、ハロゲン化シアヌル(18)及びm-フェニレンジアミン化合物(19)を適当な有機溶媒中で反応させて得ることができる。
本発明の組成物は、分子量1,000以上の架橋剤Aを含有する。これによって、保護膜の膜密度を高め、高温高湿耐性を向上させることができる。
本発明の組成物には、各種の溶媒を添加し、トリアジン環含有ハイパーブランチポリマーを溶解させて使用することが好ましい。この場合、溶媒は重合時に用いた溶媒と同じものでも別のものでもよい。この溶媒は、ポリマーとの相溶性を損なわなければ特に限定されない。
本発明の組成物には、それぞれの架橋剤に応じた開始剤を配合することもできる。なお、上述のとおり、架橋剤として多官能エポキシ化合物及び/又は多官能(メタ)アクリル化合物を用いる場合、開始剤を使用せずとも光硬化が進行して硬化膜を与えるものであるが、その場合に開始剤を使用しても差し支えない。
本発明の膜形成用組成物は、本発明の効果を損なわない限りにおいて、その他の成分、例えば、レベリング剤、界面活性剤等を含んでもよい。
本発明の透明導電膜用保護膜は、上述した透明導電膜用保護膜形成組成物を透明導電膜に塗布し、必要に応じて加熱して溶媒を蒸発させた後、加熱又は光照射することによって形成することができる。
[1H-NMR]
装置:Varian NMR System 400NB (400MHz)
JEOL-ECA700 (700MHz)
測定溶媒:DMSO-d6
基準物質:テトラメチルシラン(TMS)(δ 0.0ppm)
[GPC]
装置:東ソー(株)製HLC-8200 GPC
カラム:Shodex KF-804l+KF-805l
カラム温度:40℃
溶媒:テトラヒドロフラン(THF)
検出器:UV(254nm)
検量線:標準ポリスチレン
[エリプソメーター]
装置:ジェー・エー・ウーラム・ジャパン(株)製多入射角分光エリプソメーターVASE
[示差熱天秤(TG-DTA)]
装置:(株)リガク製TG-8120
昇温速度:10℃/分
測定温度:25-750℃
[高温高湿試験器]
装置:エスペック(株)製ライトスペック恒温(恒湿)器LHU-113
[HAZE]
装置:日本電色工業(株)製ヘーズメーターNDH5000
[光学顕微鏡]
装置:OLYMPUS(株)製研究用システム顕微鏡BX51
[非接触式シート抵抗測定器]
装置:ナプソン(株)EC-80
[膜密度測定]
装置:Bruker AXS社製多機能薄膜材料評価X線回折装置D8 DISCOVER
合成例1で得られたHB-TmDA40について、TG-DTA測定の結果を図2に示す。5%重量減少は419℃であった。
(2)屈折率測定
合成例1で得られたHB-TmDA40 0.5gを、シクロヘキサノン4.5gに溶解し、薄黄色透明溶液を得た。得られた溶液をガラス基板上にスピンコーターを用いて200rpmで5秒間、2,000rpmで30秒間スピンコートし、150℃で1分、250℃で5分間加熱して溶媒を除去し、膜厚500nmの被膜を得た。得られた被膜の屈折率を測定したところ、550nmにおける屈折率は1.790であった。
合成例1で得られたHB-TmDA40 100gをシクロヘキサノン384.0g、イオン交換水16.0gの混合溶媒に溶解させ、20質量%の溶液(以下、HB-TmDA40V1という。)を調製した。
銀ナノワイヤ分散液50g(ClearOhm、Cambrios Technologies Corporation社製)をイソプロピルアルコール50gで希釈し、導電性インクAを調製した。
調製例2で調製した導電性インクAを、無アルカリガラス基板上にスピンコート法で200rpm、5秒、その後900rpm、30秒で成膜した後に、ホットプレート上で120℃、1分乾燥し、透明導電膜を作製した。
調製例1で調製したHB-TmDA40V1 5.0g、10質量%シクロヘキサノン溶液のA-9300(分子量423、新中村化学工業(株)製)0.5g、60質量%シクロヘキサノン溶液のエトキシ化ペンタエリスリトールテトラアクリレート(ATM-35E、350mPa・s、分子量1,892、新中村化学工業(株)製)0.167g、5質量%シクロヘキサノン溶液の光ラジカル開始剤イルガキュア184(BASF社製)1.6g、1質量%シクロヘキサノン溶液の界面活性剤メガファックR-30-N(DIC(株)製)0.05g、イオン交換水1.35g、及びシクロヘキサノン32.4gを加え、目視で溶解したことを確認して総固形分濃度3質量%のワニス(以下、HB-TmDA40VF1という。)を調製した。
調製例1で調製したHB-TmDA40V1 1.0g、10質量%シクロヘキサノン溶液のM-403[5官能アクリレート(分子量524)と6官能アクリレート(分子量579)との混合物、東亞合成(株)製]0.4g、10質量%シクロヘキサノン溶液のエトキシ化ペンタエリスリトールテトラアクリレート(ATM-35E、350mPa・s、分子量1,892、新中村化学工業(株)製)0.2g、5質量%シクロヘキサノン溶液の光ラジカル開始剤イルガキュア184(BASF社製)0.32g、1質量%シクロヘキサノン溶液の界面活性剤メガファックR-30-N(DIC(株)製)0.01g、イオン交換水0.29g、及びシクロヘキサノン8.47gを加え、目視で溶解したことを確認して総固形分濃度3質量%のワニス(以下、HB-TmDA40VF2という。)を調製した。
調製例1で調製したHB-TmDA40V1 1.0g、60質量%シクロヘキサノン溶液のエトキシ化グリセリントリアクリレート(A-GLY-20E、200mPa・s、分子量1,295、新中村化学工業(株)製)0.033g、60質量%シクロヘキサノン溶液のエトキシ化ペンタエリスリトールテトラアクリレート(ATM-35E、分子量1,892、350mPa・s、新中村化学工業(株)製)0.033g、5質量%シクロヘキサノン溶液の光ラジカル開始剤イルガキュア184(BASF社製)0.32g、1質量%シクロヘキサノン溶液の界面活性剤メガファックR-30-N(DIC(株)製)0.01g、イオン交換水0.37g、及びシクロヘキサノン8.47gを加え、目視で溶解したことを確認して総固形分濃度3質量%のワニス(以下、HB-TmDA40VF3という。)を調製した。
実施例1~3で調製した各ワニスをソーダライムシリカガラス基板上にスピンコーターを用いて200rpmで5秒、1,000rpmで30秒スピンコートし、オーブンを用いて130℃で3分間の焼成を行った。その後、高圧水銀ランプを用いて、大気下(実施例4及び6)又は窒素雰囲気下(実施例5)で、積算露光量400mJ/cm2で硬化させ、膜厚100nmの硬化膜を得た。得られた膜の屈折率の測定結果を表1に示す。
実施例1~3で調製した各ワニスをシリコンウエハ基板上にスピンコーターを用いて200rpmで5秒、1,000rpmで30秒スピンコートし、オーブンを用いて130℃で3分の焼成を行った。その後、高圧水銀ランプを用いて、大気下又は窒素雰囲気下で、積算露光量400mJ/cm2で硬化させて、膜厚100nmの硬化膜を得た。これらの硬化膜についてXRR測定を行い、膜密度を算出した。表2に、各実施例において使用したワニス、露光環境、膜密度の測定結果を示す。
調製例3で作製した透明導電膜上に、実施例1~3で調製した各ワニスを固形分2%になるようにシクロヘキサノンにて希釈し、スピンコーターを用いて200rpmで5秒、1,000rpmで30秒スピンコートし、オーブンを用いて130℃で3分の焼成を行った。その後、高圧水銀ランプを用いて、大気下又は窒素雰囲気下で、積算露光量400mJ/cm2で硬化させて、膜厚50nmの保護膜を形成し、ヘイズ値を測定した(実施例10~14)。なお、比較例1として調製例3で作製した透明導電膜そのもののヘイズ値を測定した。表3に、各実施例において使用したワニス、露光環境、及び実施例、比較例で測定したヘイズ値の測定結果を示す。
合成例1で得られたHB-TmDA40 100gをシクロペンタノン384.0g、イオン交換水16.0gの混合溶媒に溶解させ、20質量%の溶液(以下、HB-TmDA40VP1という。)を調製した。
調製例4で調製したHB-TmDA40VP1 0.08g、10質量%シクロペンタノン/イオン交換水(96/4)混合溶液のDN0075(3,000~5,000mPa・s、日本化薬(株)製)0.78g、10質量%シクロペンタノン/イオン交換水(96/4)混合溶液のエトキシ化ペンタエリスリトールテトラアクリレート(ATM-35E、分子量1,892、350mPa・s、新中村化学工業(株)製)0.033g、5質量%シクロヘキサノン溶液の光ラジカル開始剤イルガキュア127(BASF社製)0.06g、1質量%シクロヘキサノン溶液の界面活性剤メガファックR-40(DIC(株)製)0.002g、イオン交換水0.16g、及びシクロヘキサノン3.88gを加え、目視で溶解したことを確認して総固形分濃度2質量%のワニス(以下、HB-TmDA40VPF1という。)を調製した。
実施例15で調製したHB-TmDA40VPF1をソーダライムガラス基板上にスピンコーターを用いて200rpmで5秒、1,500rpmで30秒スピンコートし、オーブンを用いて120℃で3分間の焼成を行った。その後、高圧水銀ランプを用いて、窒素下で、積算露光量400mJ/cm2で硬化させ、膜厚57nmの硬化膜を得た。得られた膜の屈折率は1.5683(波長550nm)であった。
調製例3で作製した透明導電膜上に、実施例15で調製したHB-TmDA40VPF1を、スピンコーターを用いて200rpmで5秒、1,500rpmで30秒スピンコートし、オーブンを用いて120℃で3分の焼成を行った。その後、高圧水銀ランプを用いて、窒素雰囲気下で積算露光量400mJ/cm2で硬化させて、膜厚80nmの保護膜を形成し、ヘイズ値を測定した結果、0.74%であった。
実施例17で得られた試料を槽内温度85℃、相対湿度85%に設定した恒温恒湿試験器中に入れて168、500時間保持した後の、シート抵抗変化を測定した。その結果を表5に示す。なお、表5中0hとは、試料作製直後のシート抵抗を示す。
Claims (13)
- 下記式(1)で表される繰り返し単位構造を含むトリアジン環含有ハイパーブランチポリマー及び分子量1,000以上の架橋剤Aを含有することを特徴とする透明導電膜用保護膜形成組成物。
Arは、式(2)~(13)で示される基からなる群から選ばれる少なくとも1種の基を表す。
R93及びR94は、水素原子又は炭素数1~10のアルキル基を表し、
W1及びW2は、それぞれ独立に、単結合、-C(R95)(R96)-(R95及びR96は、それぞれ独立に、水素原子又は炭素数1~10のアルキル基を表し、R95及びR96がともにアルキル基である場合、これらは互いに結合してこれらが結合する炭素原子とともに環を形成してもよい。)、-C(O)-、-O-、-S-、-S(O)-、-S(O)2-又は-N(R97)-(R97は、水素原子又は炭素数1~10のアルキル基を表す。)を表し、
X1及びX2は、それぞれ独立に、単結合、炭素数1~10のアルキレン基又は式(14)で表される基を表す。
Y1及びY2は、それぞれ独立に、単結合又は炭素数1~10のアルキレン基を表す。)]} - 架橋剤Aが多官能(メタ)アクリル化合物である請求項1記載の組成物。
- 架橋剤Aを前記トリアジン環含有ハイパーブランチポリマー100質量部に対して0.1~30質量部含む請求項1又は2記載の組成物。
- 更に、分子量1,000未満の架橋剤Bを含有する請求項1~3のいずれか1項記載の組成物。
- 架橋剤Bが、多官能(メタ)アクリル化合物である請求項4記載の組成物。
- 架橋剤Bを架橋剤A100質量部に対して0.5~400質量部含む請求項4又は5記載の組成物。
- 更に溶媒を含む請求項1~6のいずれか1項記載の組成物。
- 請求項1~7のいずれか1項記載の組成物を硬化させて得られる透明導電膜用保護膜。
- 透明導電膜が導電性ナノ構造を有する透明導電膜である請求項8記載の保護膜。
- 導電性ナノ構造が銀ナノワイヤである請求項9記載の保護膜。
- 透明導電膜と該透明導電膜上に形成された請求項8記載の保護膜とを備える透明電極。
- 透明導電膜と該透明導電膜上に形成された請求項8記載の保護膜とを備える電子デバイス。
- 有機エレクトロルミネッセンスディスプレイである請求項12記載の電子デバイス。
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CN201480075526.4A CN105980497A (zh) | 2013-12-17 | 2014-12-17 | 透明导电膜用保护膜形成组合物 |
KR1020167018913A KR20160099637A (ko) | 2013-12-17 | 2014-12-17 | 투명 도전막용 보호막 형성 조성물 |
US15/105,405 US10266701B2 (en) | 2013-12-17 | 2014-12-17 | Composition for forming protective film for transparent conductive film |
JP2015553571A JP6645188B2 (ja) | 2013-12-17 | 2014-12-17 | 透明導電膜用保護膜形成組成物 |
EP14871090.8A EP3085750A4 (en) | 2013-12-17 | 2014-12-17 | Composition for forming protective film for transparent conductive film |
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CN109072009A (zh) * | 2016-04-28 | 2018-12-21 | 琳得科株式会社 | 保护膜形成用膜及保护膜形成用复合片 |
WO2018106531A1 (en) * | 2016-12-05 | 2018-06-14 | Arkema Inc. | Initiator blends and photocurable compositions containing such initiator blends useful for 3d printing |
KR102002881B1 (ko) | 2017-06-08 | 2019-10-01 | 마이크로크래프트코리아 주식회사 | 잉크젯용 수지 조성물 및 이를 이용하여 제조된 인쇄 배선판 |
JP7136119B2 (ja) * | 2017-11-08 | 2022-09-13 | 日産化学株式会社 | トリアジン環含有重合体およびそれを含む組成物 |
CN108389943B (zh) * | 2018-02-27 | 2019-07-26 | 苏州星烁纳米科技有限公司 | 量子点发光二极管及其制备方法 |
US11795270B2 (en) * | 2019-10-25 | 2023-10-24 | Nissan Chemical Corporation | Triazine ring-containing polymer and film forming composition containing same |
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EP3085750A4 (en) | 2017-07-26 |
TWI676653B (zh) | 2019-11-11 |
EP3085750A1 (en) | 2016-10-26 |
US10266701B2 (en) | 2019-04-23 |
CN105980497A (zh) | 2016-09-28 |
US20160319132A1 (en) | 2016-11-03 |
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