WO2017094643A1 - Polymère à cycle triazine et composition filmogène le contenant - Google Patents

Polymère à cycle triazine et composition filmogène le contenant Download PDF

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WO2017094643A1
WO2017094643A1 PCT/JP2016/085112 JP2016085112W WO2017094643A1 WO 2017094643 A1 WO2017094643 A1 WO 2017094643A1 JP 2016085112 W JP2016085112 W JP 2016085112W WO 2017094643 A1 WO2017094643 A1 WO 2017094643A1
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group
carbon atoms
film
triazine ring
containing polymer
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PCT/JP2016/085112
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Japanese (ja)
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直也 西村
高大 忰山
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日産化学工業株式会社
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids
    • C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/02—Polyamines

Definitions

  • the present invention relates to a triazine ring-containing polymer and a film-forming composition containing the same.
  • a polymer containing a repeating unit having a triazine ring and an aromatic ring has a high refractive index, and the polymer alone has high heat resistance, high transparency, high refractive index, and high solubility. It has already been found that a low volume shrinkage can be achieved and it is suitable as a film-forming composition for producing an electronic device (Patent Document 1).
  • a low polarity solvent or the like may be used as a line washing solvent for the apparatus, and a polymer having low solubility in such a solvent. In some cases, the line could become clogged.
  • the present invention has been made in view of the above circumstances, and can form a thin film having a high refractive index and excellent transparency, and can be dissolved in various organic solvents such as a low polarity solvent, a hydrophobic solvent, and a low boiling point solvent.
  • An object of the present invention is to provide a triazine ring-containing polymer having excellent properties and a film-forming composition containing the same.
  • the present inventors have used a linear triazine ring-containing polymer having a fluorine atom-containing arylamino group on the triazine ring, so that it has a high refractive index and is transparent.
  • the present invention has been completed by finding that a triazine ring-containing polymer having excellent solubility in various organic solvents can be obtained.
  • a triazine ring-containing polymer comprising a repeating unit structure represented by the following formula (1): ⁇ In the formula, R and R 'each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or an aralkyl group; Ar' represents a fluorine atom-containing arylamino group; It represents at least one selected from the group represented by (2) to (13).
  • R 1 to R 92 are independently of each other a hydrogen atom, a halogen atom, a carboxyl group, a sulfo group, an alkyl group which may have a branched structure having 1 to 10 carbon atoms, or a carbon number of 1
  • R 93 and R 94 represent a hydrogen atom or an alkyl group which may have a branched structure of 1 to 10 carbon atoms
  • W 1 and W 2 is independently a single bond
  • CR 95 R 96 R 95 and R 96 are each independently a hydrogen atom or an alkyl group optionally having a branched structure of 1 to 10 carbon atoms ( However, these may be combined to form a ring.))
  • C ⁇ O, O, S, SO, SO 2 , or NR 97 R 97 is a hydrogen atom or a carbon number of 1).
  • X 1 Contact Fine X 2 are independently of each other a single bond, an alkylene group which may have a branched structure having 1 to 10 carbon atoms, or the formula, (14) (Wherein R 98 to R 101 are each independently a hydrogen atom, a halogen atom, a carboxyl group, a sulfo group, an alkyl group which may have a branched structure having 1 to 10 carbon atoms, or 1 carbon atom) Represents an alkoxy group which may have a branched structure of ⁇ 10, Y 1 and Y 2 each independently represent an alkylene group which may have a single bond or a branched structure having 1 to 10 carbon atoms.
  • the triazine ring-containing polymer of 3 wherein the fluorine atom-containing arylamino group is represented by the formula (16): (Wherein R 102 represents the same meaning as described above.) 5).
  • a film-forming composition comprising the triazine ring-containing polymer of any one of 1 to 6 and an organic solvent; 8). 7. The film-forming composition according to 7, wherein the organic solvent is at least one selected from glycol ester solvents, ketone solvents, and ester solvents, 9. 7 or 8 film-forming composition further comprising a crosslinking agent, 10. 9 the film-forming composition, wherein the crosslinking agent is a polyfunctional (meth) acrylic compound; 11. A thin film obtained from any of the film-forming compositions of 7 to 10, 12 An electronic device comprising a substrate and eleven thin films formed on the substrate; 13. An optical member comprising a base material and eleven thin films formed on the base material is provided.
  • a triazine ring-containing polymer that can form a thin film having a high refractive index and excellent transparency and excellent solubility in various organic solvents such as a low polarity solvent, a hydrophobic solvent, and a low boiling point solvent.
  • various organic solvents such as a low polarity solvent, a hydrophobic solvent, and a low boiling point solvent.
  • the triazine ring-containing polymer of the present invention also has a fluorine atom introduced therein. Regardless, the refractive index exceeding 1.7 is maintained.
  • a composition can be prepared using an organic solvent having a low solubility, such as a low polarity solvent and a hydrophobic solvent, and therefore a group that is easily eroded by a high polarity solvent.
  • a thin film can be formed on the material without any problem.
  • a thin film produced from the film-forming composition of the present invention can exhibit characteristics such as high heat resistance, high refractive index, and low volume shrinkage.
  • a liquid crystal display an organic electroluminescence (EL) display, a touch panel, an optical semiconductor ( LED) devices, solid-state imaging devices, organic thin-film solar cells, dye-sensitized solar cells, organic thin-film transistors (TFTs), lenses, prisms, cameras, binoculars, microscopes, one member for manufacturing semiconductor exposure devices, and other electronic devices And can be suitably used in the field of optical materials.
  • a thin film produced from the film-forming composition of the present invention has high transparency and a high refractive index, visibility is improved by using it as a protective film for transparent conductive films such as ITO and silver nanowires. And the deterioration thereof can be suppressed.
  • FIG. 1 is a 1 H-NMR spectrum diagram of a polymer compound [4] obtained in Example 1-1.
  • FIG. 1 is a 1 H-NMR spectrum diagram of a polymer compound [4] obtained in Example 1-1.
  • FIG. 1 is a 1 H-NMR spectrum diagram of a polymer compound [4] obtained in Example 1-1.
  • the triazine ring-containing polymer according to the present invention includes a repeating unit structure 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.
  • both of them may be hydrogen atoms.
  • the number of carbon atoms of the alkyl group is not particularly limited, but is preferably 1 to 20, and more preferably 1 to 10 carbon atoms in view of further improving the heat resistance of the polymer. Is even more preferable.
  • the structure may be any of a chain, a branch, and a ring.
  • alkyl group examples include methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, s-butyl, t-butyl, cyclobutyl, 1-methyl-cyclopropyl, 2-methyl-cyclopropyl.
  • N-pentyl 1-methyl-n-butyl, 2-methyl-n-butyl, 3-methyl-n-butyl, 1,1-dimethyl-n-propyl, 1,2-dimethyl-n-propyl, 2 , 2-dimethyl-n-propyl, 1-ethyl-n-propyl, cyclopentyl, 1-methyl-cyclobutyl, 2-methyl-cyclobutyl, 3-methyl-cyclobutyl, 1,2-dimethyl-cyclopropyl, 2,3- Dimethyl-cyclopropyl, 1-ethyl-cyclopropyl, 2-ethyl-cyclopropyl, n-hexyl, 1-methyl-n-pe Til, 2-methyl-n-pentyl, 3-methyl-n-pentyl, 4-methyl-n-pentyl, 1,1-dimethyl-n-butyl, 1,2-dimethyl-n-butyl, 1,3- Dimethyl-n-butyl, 2,2-di
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20, and more preferably 1 to 10 carbon atoms, more preferably 1 to 3 carbon atoms in view of further improving the heat resistance of the polymer. preferable.
  • the structure of the alkyl moiety may be any of a chain, a branch, and a ring.
  • alkoxy group examples include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, n-pentoxy, 1-methyl-n-butoxy, 2-methyl-n -Butoxy, 3-methyl-n-butoxy, 1,1-dimethyl-n-propoxy, 1,2-dimethyl-n-propoxy, 2,2-dimethyl-n-propoxy, 1-ethyl-n-propoxy, n -Hexyloxy, 1-methyl-n-pentyloxy, 2-methyl-n-pentyloxy, 3-methyl-n-pentyloxy, 4-methyl-n-pentyloxy, 1,1-dimethyl-n-butoxy, 1,2-dimethyl-n-butoxy, 1,3-dimethyl-n-butoxy, 2,2-dimethyl-n-butoxy, 2,3-dimethyl-n-butoxy 3,3-dimethyl-n-butoxy, 1-ethoxy,
  • the number of carbon atoms of the aryl group is not particularly limited, but is preferably 6 to 40. In view of further improving the heat resistance of the polymer, 6 to 16 carbon atoms are more preferable, and 6 to 13 are even more preferable. preferable.
  • aryl group examples include phenyl, o-chlorophenyl, m-chlorophenyl, p-chlorophenyl, o-fluorophenyl, p-fluorophenyl, o-methoxyphenyl, p-methoxyphenyl, p-nitrophenyl, p-cyanophenyl, ⁇ -naphthyl, ⁇ -naphthyl, o-biphenylyl, m-biphenylyl, p-biphenylyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4 -Phenanthryl, 9-phenanthryl group and the like.
  • the number of carbon atoms of the aralkyl group is not particularly limited, but preferably 7 to 20 carbon atoms, and the alkyl portion may be linear, branched or cyclic. Specific examples thereof include benzyl, p-methylphenylmethyl, m-methylphenylmethyl, o-ethylphenylmethyl, m-ethylphenylmethyl, p-ethylphenylmethyl, 2-propylphenylmethyl, 4-isopropylphenylmethyl, Examples include 4-isobutylphenylmethyl, ⁇ -naphthylmethyl group and the like.
  • Ar represents at least one selected from the group represented by formulas (2) to (13).
  • R 1 to R 92 are independently of each other a hydrogen atom, a halogen atom, a carboxyl group, a sulfo group, an alkyl group that may have a branched structure having 1 to 10 carbon atoms, or a group having 1 to 10 carbon atoms.
  • R 93 and R 94 represent a hydrogen atom or an alkyl group which may have a branched structure having 1 to 10 carbon atoms
  • W 1 and W 2 represent Independent of each other, a single bond
  • CR 95 R 96 R 95 and R 96 are each independently a hydrogen atom or an alkyl group optionally having a branched structure of 1 to 10 carbon atoms (however, these May be combined to form a ring.)
  • C ⁇ O, O, S, SO, SO 2 , or NR 97 R 97 is a hydrogen atom or having 1 to 10 carbon atoms
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • alkyl group and alkoxy group are the same as those described above.
  • X 1 and X 2 each independently represent a single bond, an alkylene group which may have a branched structure having 1 to 10 carbon atoms, or a group represented by the formula (14).
  • R 98 to R 101 are each independently a hydrogen atom, a halogen atom, a carboxyl group, a sulfo group, an alkyl group which may have a branched structure having 1 to 10 carbon atoms, or a carbon atom having 1 to 10 carbon atoms.
  • An alkoxy group which may have a branched structure is represented, and Y 1 and Y 2 each independently represent an alkylene group which may have a single bond or a branched structure having 1 to 10 carbon atoms.
  • Examples of the halogen atom, alkyl group and alkoxy group are the same as those described above.
  • Examples of the alkylene group that may have a branched structure having 1 to 10 carbon atoms include methylene, ethylene, propylene, trimethylene, tetramethylene, and pentamethylene groups.
  • R 1 to R 92 and R 98 to R 101 a hydrogen atom, a halogen atom, a sulfo group, an alkyl group which may have a branched structure having 1 to 5 carbon atoms, or a carbon number of 1 to The alkoxy group which may have 5 branched structures is preferable, and a hydrogen atom is more preferable.
  • Ar is preferably at least one of the formulas (2), (5) to (13), and the formulas (2), (5), (7), (8), (11) to (13) More preferably, at least one selected from Specific examples of the aryl group represented by the above formulas (2) to (13) include, but are not limited to, those represented by the following formulae.
  • an aryl group represented by the following formula is more preferable because a polymer having a higher refractive index can be obtained.
  • Ar is preferably an m-phenylene group represented by the formula (17).
  • Ar ′ is a fluorine atom-containing arylamino group
  • examples of the aryl group include the same groups as those described above, and a phenyl group is particularly preferable.
  • the fluorine atom-containing group include fluorine atom-containing hydrocarbon groups such as a fluorine atom and a fluoroalkyl group, and a fluorine atom and a fluoroalkyl group having 1 to 10 carbon atoms are preferable.
  • the fluoroalkyl group having 1 to 10 carbon atoms may be linear, branched or cyclic, for example, trifluoromethyl group, pentafluoroethyl group, 2,2,2-trifluoroethyl group, heptafluoropropyl group 2,2,3,3,3-pentafluoropropyl group, 2,2,3,3-tetrafluoropropyl group, 2,2,2-trifluoro-1- (trifluoromethyl) ethyl group, nonafluoro Butyl group, 4,4,4-trifluorobutyl group, undecafluoropentyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, 2,2,3,3 , 4,4,5,5-octafluoropentyl group, tridecafluorohexyl group, 2,2,3,3,4,5,5,6,6,6-undecafluorohexyl group, 2, 2, 3, 3, 4, 4 5,5,6,6- de
  • a perfluoroalkyl group having 1 to 10 carbon atoms is preferable, and in particular, a perfluoroalkyl group having 1 to 5 carbon atoms.
  • a fluoroalkyl group is more preferred, and a trifluoromethyl group is most preferred.
  • the number of fluorine atom-containing groups is not particularly limited and can be any number that can be substituted on the aryl group. However, considering the balance between refractive index maintenance and solubility in a solvent, 1 to 4 One is preferable, one to two is more preferable, and one is even more preferable.
  • Suitable examples of the fluorine-containing arylamino group include those represented by the formula (15), and particularly preferred are those represented by the formula (16) having a fluorine atom-containing group in the para position with respect to the amino group.
  • R 102 represents a fluorine atom or a fluoroalkyl group having 1 to 10 carbon atoms.
  • R 102 represents the same meaning as described above.
  • fluorine-containing arylamino group examples include those represented by the following formula, but are not limited thereto.
  • a fluorine atom containing arylamino group can be introduce
  • the fluorine atom-containing arylamino compound include 4-fluoroaniline, 4-trifluoromethylaniline, 4-pentafluoroethylaniline and the like.
  • triazine ring-containing polymers include those represented by the formulas (18) to (21).
  • R 102 represents the same meaning as described above.
  • R 102 represents the same meaning as described above.
  • the weight average molecular weight of the polymer in the present invention is not particularly limited, but is preferably 500 to 500,000, more preferably 500 to 100,000, further improving heat resistance and reducing shrinkage. In view of the above, 2,000 or more is preferable, 50,000 or less is preferable, 30,000 or less is more preferable, 10,000 or less is more preferable in terms of further improving the solubility and decreasing the viscosity of the obtained solution. Even more preferred.
  • the weight average molecular weight in this invention is an average molecular weight obtained by standard polystyrene conversion by gel permeation chromatography (henceforth GPC) analysis.
  • the triazine ring-containing polymer of the present invention can be produced according to the technique disclosed in Patent Document 1 described above.
  • the triazine ring-containing polymer (20) is obtained by reacting the triazine compound (22) with the fluorine atom-containing aniline compound (24) in a suitable organic solvent, It can be obtained by reacting with an aryl diamino compound (23).
  • the amount of the fluorine atom-containing aniline compound (24) used is preferably about 0.05 to 0.5 equivalent, more preferably 0.1 to 0.4 equivalent, relative to 1 equivalent of the halogen atom of the triazine compound.
  • the charge ratio of the aryldiamino compound (23) is arbitrary as long as the target polymer can be obtained, but 0.01 to 10 equivalents of the aryldiamino compound (23) with respect to 1 equivalent of the triazine compound (22). Preferably, 1 to 5 equivalents are more preferable.
  • the aryldiamino compound (23) may be added neat or in a solution dissolved in an organic solvent, but the latter method is preferred in view of ease of operation and ease of reaction control.
  • the reaction temperature may be appropriately set in the range from the melting point of the solvent to be used to the boiling point of the solvent, but is preferably about ⁇ 30 to 150 ° C., more preferably ⁇ 10 to 100 ° C.
  • 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, Hexamethylphosphoramide, N, N-dimethylacetamide, N-methyl-2-piperidone, N, N-dimethylethyleneurea, N, N, N ′, N′-tetramethylmalonic acid amide, N-methylcaprolactam, N-acetylpyrrolidine, N, N-diethylacetamide, N-ethyl-2-pyrrolidone, N, N-dimethylpropionic acid amide, N, N-dimethylisobutyramide, N-methylformamide, N, N'-dimethylpropylene urea Amide solvents such as, and mixed solvents thereof Among these, N, N-dimethylformamide, dimethyl s thereof,
  • 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, n-propylamine, trimethylamine, triethylamine, diisopropylamine, diisopropylethylamine, N-methylpiperidine, Examples include 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 and more preferably 1 to 10 equivalents with respect to 1 equivalent of the triazine compound (22). These bases may be used as an aqueous solution. Although it is preferable that the raw material component does not remain in the obtained polymer, a part of the raw material may remain as long as the effect of the present invention is not impaired. After completion of the reaction, the product can be easily purified by a reprecipitation method or the like.
  • the above-described triazine ring-containing polymer of the present invention can be suitably used as a film-forming composition.
  • a crosslinking agent may be added.
  • the crosslinking agent is not particularly limited as long as it is a compound having a substituent capable of reacting with the above-described triazine ring-containing polymer. Examples of such compounds include melamine compounds having a crosslinkable substituent such as a methylol group and methoxymethyl group, substituted urea compounds, compounds containing a crosslinkable substituent such as an epoxy group or an oxetane group, and blocked isocyanates.
  • a compound containing a group is preferred, and in particular, a compound having a blocked isocyanate group, and a polyfunctional epoxy compound and / or a polyfunctional (meth) acrylic compound that gives a photocurable composition without using an initiator are preferred.
  • These compounds may have at least one crosslink forming substituent when used for polymer terminal treatment, and at least two crosslink forming substituents when used for cross-linking treatment between polymers. It is necessary to have.
  • the polyfunctional epoxy compound is not particularly limited as long as it has two or more epoxy groups in one molecule. Specific examples 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, YH434L (manufactured by Tohto Kasei Co., Ltd.), epoxy resins having a cyclohexene oxide structure, Epolide GT-401 and GT -403, GT-301, GT-302, Celoxide 2021, 3000 (manufactured by Daicel Chemical Industries, Ltd.), bisphenol A type epoxy resin, Epicoat (currently jER) 1001, 1002, 1003, 1004, 1007, 1009, 1010, 828 (Japan Epoxy Resin Co., Ltd.), Bisphenol F type epoxy resin, Epicoat (currently jER) 807 (Japan Epoxy Resin Co., Ltd.) , Epicoat (a phenol novolac type epoxy resin) , JER) 152, 154 (above, manufactured by Japan Epoxy Resins Co., Ltd.), EPPN 201, 202 (above, manufactured by Nippon Kayaku Co., Ltd.
  • 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 include ethylene glycol diacrylate, ethylene glycol dimethacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, ethoxylated bisphenol A diacrylate, ethoxylated bisphenol A dimethacrylate, ethoxylated trimethylolpropane triacrylate, and ethoxylated.
  • Polyfunctional (meth) acrylic compounds can be obtained as commercial products. Specific examples thereof include NK ester A-200, same A-400, same A-600, same A-1000, same A- 9300 (Tris (2-acryloyloxyethyl) isocyanurate), A-9300-1CL, A-TMPT, 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, AT PT-9EO, AT-20E, ATM-4E, ATM-35E (Shin Nakamura Chemical Co., Ltd.), KAYARAD (registered trademark) DPEA-12, PEG400DA,
  • 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, hexahydroanhydride.
  • the isocyanate group (—NCO) when the isocyanate group (—NCO) has two or more blocked isocyanate groups blocked by an appropriate protective group in one molecule, it is exposed to a high temperature during thermosetting.
  • the protective group (block part) is not particularly limited as long as it is dissociated by thermal dissociation and the resulting isocyanate group causes a crosslinking reaction with the resin.
  • a group represented by the following formula Examples thereof include compounds having two or more in the molecule (note that 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.
  • the compound having two or more isocyanate groups in one molecule include, for example, isophorone diisocyanate, 1,6-hexamethylene diisocyanate, methylene bis (4-cyclohexyl isocyanate), polyisocyanate of trimethylhexamethylene diisocyanate, and dimers thereof. , 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 , P-chlorophenol, phenols such as 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, benzophenone oxime
  • pyrazoles such as pyrazole, 3,5-dimethylpyrazole and 3-methylpyrazole
  • thiols such as dodecanethiol and benzenethiol.
  • 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 Polyurethane Co., Ltd.), Duranate (registered trademark) 17B-60PX, TPA-B80E, MF-B60X, MF-K60X, E402-B80T (above, manufactured by Asahi Kasei Chemicals Corporation), Karenz MOI-BM (registered trademark) (above, manufactured by Showa Denko Co., Ltd.), BI-7950, BI-7951, BI-7960, BI-7916, BI-7963, BI-7982, BI-7991, BI-7992 (manufactured by Baxenden chemicals LTD) And the like.
  • the aminoplast compound is not particularly limited as long as it has two or more methoxymethylene groups in one molecule.
  • hexamethoxymethylmelamine CYMEL (registered trademark) 303 tetrabutoxymethylglycoluril 1170 Cymel series such as Tetramethoxymethylbenzoguanamine 1123 (Nippon Cytec Industries, Ltd.), Nicalac (registered trademark) MW-30HM, MW-390, MW-100LM, which are methylated melamine resins
  • melamine compounds such as MX-750LM, Nicarac series such as MX-270 and MX-280, which are methylated urea resins, and MX-280 and MX-290 (manufactured by Sanwa Chemical Co., Ltd.).
  • 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 oxetanyl group above And Toa Gosei Co., Ltd..
  • the phenoplast compound has two or more hydroxymethylene groups in one molecule and undergoes a crosslinking reaction by a dehydration condensation reaction with the polymer of the present invention when exposed to a high temperature during thermosetting. It is.
  • 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, and specific examples thereof include 26DMPC, 46DMOC, DM-BIPC-F, DM-BIOC-F, TM-BIP-A, BISA-F, BI25X-DF. BI25X-TPA (above, manufactured by Asahi Organic Materials Co., Ltd.).
  • a polyfunctional (meth) acrylic compound is suitable from the viewpoint that the refractive index lowering due to the crosslinking agent blending can be suppressed and the curing reaction proceeds rapidly, and among these, the triazine ring-containing polymer is preferred. Since it is excellent in compatibility, the polyfunctional (meth) acrylic compound having the following isocyanuric acid skeleton is more preferable. Examples of the polyfunctional (meth) acrylic compound having such a skeleton include NK ester A-9300 and A-9300-1CL (both manufactured by Shin-Nakamura Chemical Co., Ltd.).
  • R 111 to R 113 are each independently a monovalent organic group having at least one (meth) acryl group at the end).
  • the resulting cured film it is liquid at 25 ° C. and its viscosity is 5000 mPa ⁇ s or less, preferably 1 To 3000 mPa ⁇ s, more preferably 1 to 1000 mPa ⁇ s, and even more preferably 1 to 500 mPa ⁇ s, a polyfunctional (meth) acrylic compound (hereinafter referred to as a low-viscosity crosslinking agent) alone or in combination of two or more.
  • a polyfunctional (meth) acrylic compound hereinafter referred to as a low-viscosity crosslinking agent
  • Such low-viscosity cross-linking agents are also commercially available.
  • NK ester A-GLY-3E 85 mPa ⁇ s, 25 ° C.
  • A-GLY -9E 95 mPa ⁇ s, 25 ° C
  • A-GLY-20E 200 mPa ⁇ s, 25 ° C
  • A-TMPT-3EO 60 mPa ⁇ s, 25 ° C
  • A-TMPT-9EO ATM
  • the chain length between (meth) acrylic groups such as -4E (150 mPa ⁇ s, 25 ° C.), ATM-35E (350 mPa ⁇ s, 25 ° C.) (manufactured by Shin-Nakamura Chemical Co., Ltd.) is relatively Long crosslinking agents.
  • NK ester A-GLY-20E (made by Shin-Nakamura Chemical Co., Ltd.) and ATM-35E (made by Shin-Nakamura Chemical Co., Ltd.)
  • a polyfunctional (meth) acrylic compound having the above isocyanuric acid skeleton in consideration of improving the alkali resistance of the cured film obtained, NK ester A-GLY-20E (made by Shin-Nakamura Chemical Co., Ltd.) and ATM-35E (made by Shin-Nakamura Chemical Co., Ltd.) ) And a polyfunctional (meth) acrylic compound having the above isocyanuric acid skeleton.
  • the thin film laminated film can be cured well without being inhibited by oxygen. Sex can be obtained.
  • the protective film since the protective film needs to be peeled after curing, it is preferable to use a polybasic acid-modified acrylic oligomer that gives a thin film with good peelability.
  • the above-mentioned cross-linking agents may be used alone or in combination of two or more.
  • the amount of the crosslinking agent used is preferably 1 to 100 parts by mass with respect to 100 parts by mass of the triazine ring-containing polymer, but considering the solvent resistance, the lower limit is preferably 2 parts by mass, more preferably 5 parts by mass. Furthermore, in consideration of controlling the refractive index, the upper limit is preferably 20 parts by mass, more preferably 15 parts by mass.
  • an initiator corresponding to each crosslinking agent can be blended.
  • a polyfunctional epoxy compound and / or 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.
  • onium salt derivatives such as diazonium salts, sulfonium salts, and iodonium salts can be used.
  • aryldiazonium salts such as phenyldiazonium hexafluorophosphate, 4-methoxyphenyldiazonium hexafluoroantimonate, 4-methylphenyldiazonium hexafluorophosphate; diphenyliodonium hexafluoroantimonate, di (4-methylphenyl) Diaryliodonium salts such as iodonium hexafluorophosphate and di (4-tert-butylphenyl) iodonium hexafluorophosphate; triphenylsulfonium hexafluoroantimonate, tris (4-methoxyphenyl) sulfonium hexafluorophosphate, diphenyl-4-thiophenoxy Phenylsulfonium hexafluoroantimonate, diphenyl-4-thiophenoxy Enylsulfonium he
  • 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 (Sanshin Chemical Industry Co., Ltd.), UVI-6950, UVI-6970, UVI-6974, UVI-6990, UVI-6990 (above, Union Carbide) Co., Ltd.), CPI-100P, CPI-100A, CPI-200K, CPI-200S (above, manufactured by San Apro Co., Ltd.), Adekaoptomer SP-150, SP-151, SP-170, SP-171 (above, Asahi Denka Kogyo Co., Ltd.), Irgacure 261 (BASF), CI-2481, CI-2624, CI-2 39, CI-2064 (above, manufactured by Nippon Soda Co., Ltd.),
  • the photobase generator may be appropriately selected from known ones, such as Co-amine complex, oxime carboxylic acid ester, carbamic acid ester, quaternary ammonium salt photobase generator.
  • a photoacid or base generator When a photoacid or base 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. If necessary, an epoxy resin curing agent may be blended in an amount of 1 to 100 parts by mass with respect to 100 parts by mass of the polyfunctional epoxy compound.
  • a radical photopolymerization initiator when a polyfunctional (meth) acrylic compound is used, a radical photopolymerization initiator can be used.
  • the radical photopolymerization initiator may be appropriately selected from known ones, such as acetophenones, benzophenones, Michler's benzoylbenzoate, amyloxime esters, oxime esters, tetramethylthiuram monosulfide, and thioxanthones. Is mentioned.
  • photocleavable photoradical polymerization initiators are preferred.
  • the photocleavable photoradical polymerization initiator is described in the latest UV curing technology (p. 159, publisher: Kazuhiro Takahisa, publisher: Technical Information Association, Inc., published in 1991).
  • radical photopolymerization initiators examples include BASF Corporation trade names: Irgacure 127, 184, 369, 379, 379EG, 651, 500, 754, 819, 903, 907, 784, 2959, CGI 1700, CGI 1750, CGI 1850. , CG24-61, OXE01, OXE02, Darocur 1116, 1173, MBF, manufactured by BASF, Inc.
  • Product name Lucirin TPO, manufactured by UCB, Inc.
  • radical photopolymerization initiator When using a radical photopolymerization initiator, it is preferably used in the range of 0.1 to 200 parts by weight, preferably in the range of 1 to 150 parts by weight, with respect to 100 parts by weight of the polyfunctional (meth) acrylate compound. Is more preferable.
  • a polyfunctional thiol compound having two or more mercapto groups in the molecule may be added to the composition of the present invention for the purpose of promoting the reaction between the triazine ring-containing polymer and the crosslinking agent. Good.
  • a polyfunctional thiol compound represented by the following formula is preferable.
  • L represents a divalent to tetravalent organic group, preferably a divalent to tetravalent aliphatic group having 2 to 12 carbon atoms or a divalent to tetravalent heterocyclic group, and preferably has 2 to 4 carbon atoms.
  • N represents an integer of 2 to 4 corresponding to the valence of L.
  • the compound examples include 1,4-bis (3-mercaptobutyryloxy) butane, 1,3,5-tris (3-mercaptobutyryloxyethyl) -1,3,5-triazine-2,4. , 6- (1H, 3H, 5H) -trione, pentaerythritol tetrakis (3-mercaptobutyrate), trimethylolpropane tris (3-mercaptobutyrate), trimethylolethane tris (3-mercaptobutyrate), etc. It is done.
  • polyfunctional thiol compounds can also be obtained as commercial products, and examples thereof include Karenz MT-BD1, Karenz MT NR1, Karenz MT PE1, TPMB, TEMB (manufactured by Showa Denko KK). These polyfunctional thiol compounds may be used alone or in combination of two or more.
  • the amount added is not particularly limited as long as it does not adversely affect the resulting thin film, but in the present invention, 0.01 to 10. 0% by mass is preferable, and 0.03 to 6.0% by mass is more preferable.
  • solvents are added to the composition of the present invention to dissolve the triazine ring-containing polymer.
  • the solvent include water, 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, dipropylene Recall monomethyl ether, diethylene glycol monomethyl ether, propylene
  • glycols such as ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, etc.
  • 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 0.1 to 40% by mass.
  • composition of the present invention includes other components other than the triazine ring-containing polymer, the crosslinking agent and the solvent, for example, a leveling agent, a surfactant, a silane coupling agent, and inorganic fine particles, as long as the effects of the present invention are not impaired. Additives such as may be included.
  • surfactant examples include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene oleyl ether; polyoxyethylene octylphenol ether, polyoxyethylene nonylphenol Polyoxyethylene alkyl allyl ethers such as ethers; polyoxyethylene / polyoxypropylene block copolymers; sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan tristearate Sorbitan fatty acid esters such as polyoxyethylene sorbitan monolaurate, polyoxyethyleneso Nonionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as bitane monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, polyoxyethylene sorbitan tristearate, trade name
  • surfactants may be used alone or in combination of two or more.
  • the amount of the surfactant used is preferably 0.0001 to 5 parts by mass, more preferably 0.001 to 1 part by mass, and 0.01 to 0.5 parts by mass with respect to 100 parts by mass of the triazine ring-containing polymer. Even more preferred.
  • the inorganic fine particles include Be, Al, Si, Ti, V, Fe, Cu, Zn, Y, Zr, Nb, Mo, In, Sn, Sb, Ta, W, Pb, Bi, and Ce.
  • examples thereof include oxides, sulfides and nitrides of one or more kinds of metals selected, and these metal oxides are particularly preferable.
  • the inorganic fine particles may be used alone or in combination of two or more.
  • Specific examples of the metal oxide include Al 2 O 3 , ZnO, TiO 2 , ZrO 2 , Fe 2 O 3 , Sb 2 O 5 , BeO, ZnO, SnO 2 , CeO 2 , SiO 2 and WO 3. It is done.
  • the composite oxide is a mixture of two or more inorganic oxides in the production stage of fine particles.
  • examples thereof include TiO 2 and ZrO 2 , TiO 2 , ZrO 2 and SnO 2 , and complex oxides of ZrO 2 and SnO 2 .
  • the compound of the said metal may be sufficient.
  • ZnSb 2 O 6 , BaTiO 3 , SrTiO 3 , SrSnO 3 and the like can be mentioned. These compounds can be used alone or in admixture of two or more, and may also be used in admixture with the above oxides.
  • the said other component can be added at the arbitrary processes at the time of preparing the composition of this invention.
  • the film-forming composition of the present invention can be applied to a substrate, then heated as necessary to evaporate the solvent, and then heated or irradiated with light to form a desired cured film.
  • the coating method of the composition is arbitrary, for example, spin coating method, dip method, flow coating method, ink jet method, jet dispenser method, spray method, bar coating method, gravure coating method, slit coating method, roll coating method, transfer Methods such as printing, brush coating, blade coating, and air knife coating can be employed.
  • a base material silicon, glass formed with indium tin oxide (ITO), glass formed with indium zinc oxide (IZO), metal nanowire, polyethylene terephthalate (PET), plastic, glass, Examples include a base material made of quartz, ceramics, and the like, and a flexible base material having flexibility can also be used.
  • the firing temperature is not particularly limited for the purpose of evaporating the solvent, and can be carried out at 110 to 400 ° C., for example.
  • the baking method is not particularly limited, and for example, it 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.
  • the conditions for the light irradiation are not particularly limited, and an appropriate irradiation energy and time may be adopted depending on the triazine ring-containing polymer and the crosslinking agent to be used.
  • the thin film and cured film of the present invention obtained as described above can achieve high heat resistance, high refractive index, and low volume shrinkage, liquid crystal displays, organic electroluminescence (EL) displays, touch panels, optical semiconductors ( LED devices, solid-state imaging devices, organic thin-film solar cells, dye-sensitized solar cells, organic thin-film transistors (TFTs), lenses, prism cameras, binoculars, microscopes, and parts for manufacturing semiconductor exposure devices, electronic devices, It can be suitably used in the field of optical materials.
  • a thin film or a cured film prepared from the composition of the present invention has high transparency and a high refractive index, and therefore, when used as a protective film for a transparent conductive film such as ITO or silver nanowire, the visibility is reduced. While improving, it can suppress degradation of a transparent conductive film.
  • 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
  • DMAc dimethylacetamide
  • CYC 2,4,6-trichloro-1,3,5-triazine
  • 4-trifluoromethylaniline [2] (16.16 g, 0.1 mol, manufactured by Tianjin Jiahan Chemical Co., Ltd.) was added dropwise with the temperature controlled to 0 ° C. or lower, and the mixture was allowed to react for 1 hour.
  • m-phenylenediamine (mPDA) [3] (11.90 g, 0.11 mol, manufactured by AminoChem) dissolved in 120.57 g of NMP was added dropwise with the flask internal temperature controlled at 30 ° C. or lower. After the dropwise addition, the mixture was heated to 90 ° C. and reacted for 1 hour, and then n-propylamine (18.32 g, manufactured by Tokyo Chemical Industry Co., Ltd.) was dropped into a reaction system controlled at 30 ° C. or lower and stirred for 1 hour. did. The obtained reaction solution was dropped into 1251 g of ion-exchanged water, and reprecipitation was performed.
  • mPDA m-phenylenediamine
  • L-TDF the target polymer compound [4]
  • the measurement result of 1 H-NMR spectrum of L-TDF is shown in FIG.
  • the obtained L-TDF is a compound having a structural unit represented by the formula (1).
  • the weight average molecular weight Mw measured by polystyrene conversion by GPC of L-TDF was 5,700, and the polydispersity Mw / Mn was 1.95.
  • Example 1-1 L-TDF obtained in Example 1-1 was dissolved in various organic solvents shown in Table 1 so as to be 10% by mass, 20% by mass, and 30% by mass, and it was visually confirmed whether there was any insoluble matter. And evaluated according to the following criteria. The results are shown in Table 1. ⁇ : All dissolved, ⁇ : Slightly cloudy, ⁇ : Precipitate
  • THF Tetrahydrofuran
  • CHN Cyclohexanone
  • PGME Propylene glycol monomethyl ether
  • MEK Methyl ethyl ketone
  • MIBK Methyl isobutyl ketone
  • Example 1-1 As shown in Table 1, it can be seen that the L-TDF obtained in Example 1-1 has good solubility in various solvents.
  • Example 2-1 Preparation of film-forming composition and film [Example 2-1] L-TDF (0.5 g) obtained in Example 1-1 was dissolved in PGME (4.5 g) to prepare a uniform transparent varnish (hereinafter referred to as L-TDFV1). The obtained L-TDFV1 was spin-coated on a glass substrate with a spin coater aiming at 500 nm, and baked on a hot plate at 120 ° C. for 3 minutes to obtain a coating (hereinafter referred to as L-TDFV1F1). Table 2 shows the refractive index and film thickness of L-TDFV1F1 produced in Example 2-1.
  • the thin film prepared from the polymer compound obtained in Example 1-1 has a refractive index exceeding 1.72.
  • the obtained L-TDFV2 was spin-coated on a glass substrate with a spin coater aiming at 250 nm and dried on a hot plate at 120 ° C. for 3 minutes. Thereafter, a cured film was obtained by irradiation with a high-pressure mercury lamp under an integrated exposure amount of 400 mJ / cm 2 under nitrogen. When the refractive index of the obtained film was measured, the refractive index at 550 nm was 1.584.
  • Example 2-3 Varnish L-TDFV1 obtained in Example 2-1 (1.79 g), DN0075 (manufactured by Nippon Kayaku Co., Ltd., 0.036 g), ATM-35E (manufactured by Shin-Nakamura Chemical Co., Ltd., 0.018 g) ), Irgacure 2959 (manufactured by BASF, 0.014 g), and Karenz MTNR1 (manufactured by Showa Denko KK, 0.54 g) prepared in advance in a 0.1% by mass n-propyl acetate solution, Megafac F-559 ( DIC Co., Ltd., 0.002 g) was mixed, and 2.85 g of n-propyl acetate was added and dissolved therein to prepare a varnish which is a homogeneous solution visually (hereinafter referred to as L-TDFV3).
  • a cured film was produced in the same manner as in Example 2-2 except that the obtained L-

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Abstract

Cette invention concerne un polymère à cycle triazine contenant une structure à motif de répétition représentée, par exemple, par la formule [4], ayant un indice de réfraction élevé et une excellente solubilité dans divers solvants organiques tels que les solvants à faible polarité, les solvants hydrophobes, et les solvants à bas point d'ébullition, et un film mince ayant un indice de réfraction élevé et une excellente transparence qui peut être formé à l'aide d'une composition contenant ledit polymère à cycle triazine.
PCT/JP2016/085112 2015-11-30 2016-11-28 Polymère à cycle triazine et composition filmogène le contenant WO2017094643A1 (fr)

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WO2020022410A1 (fr) * 2018-07-26 2020-01-30 日産化学株式会社 Composition pour former un film protecteur pour film conducteur transparent
JP2020164868A (ja) * 2019-03-29 2020-10-08 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膜形成用組成物
WO2021079991A1 (fr) * 2019-10-25 2021-04-29 日産化学株式会社 Polymère contenant un cycle triazine et composition filmogène le contenant

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CN110957057A (zh) 2019-11-14 2020-04-03 宸盛光电有限公司 具自组装保护层之导电结构及自组装涂层组合物

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WO2020022410A1 (fr) * 2018-07-26 2020-01-30 日産化学株式会社 Composition pour former un film protecteur pour film conducteur transparent
JPWO2020022410A1 (ja) * 2018-07-26 2021-08-05 日産化学株式会社 透明導電膜用保護膜形成組成物
JP2020164868A (ja) * 2019-03-29 2020-10-08 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膜形成用組成物
JP7484332B2 (ja) 2019-03-29 2024-05-16 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膜形成用組成物
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