CN105683225A - Polymerizable monomer, polymer compound, photocurable resin composition, sealing element for liquid crystal display element, vertical conduction material, and liquid crystal display element - Google Patents
Polymerizable monomer, polymer compound, photocurable resin composition, sealing element for liquid crystal display element, vertical conduction material, and liquid crystal display element Download PDFInfo
- Publication number
- CN105683225A CN105683225A CN201480058891.4A CN201480058891A CN105683225A CN 105683225 A CN105683225 A CN 105683225A CN 201480058891 A CN201480058891 A CN 201480058891A CN 105683225 A CN105683225 A CN 105683225A
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- China
- Prior art keywords
- liquid crystal
- methyl
- compound
- crystal display
- mentioned
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 136
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 110
- 239000000178 monomer Substances 0.000 title claims abstract description 72
- 239000011342 resin composition Substances 0.000 title claims abstract description 53
- 238000007789 sealing Methods 0.000 title abstract description 30
- 239000000463 material Substances 0.000 title abstract description 5
- 229920000642 polymer Polymers 0.000 title abstract description 5
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims abstract description 33
- 125000005370 alkoxysilyl group Chemical group 0.000 claims abstract description 7
- 125000000524 functional group Chemical group 0.000 claims abstract description 7
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- 238000004519 manufacturing process Methods 0.000 claims description 56
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 54
- 239000003566 sealing material Substances 0.000 claims description 43
- 239000004593 Epoxy Substances 0.000 claims description 32
- 238000006116 polymerization reaction Methods 0.000 claims description 32
- 239000005711 Benzoic acid Substances 0.000 claims description 27
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
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- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- WCZHHZGITDJUQI-UHFFFAOYSA-N ethane-1,2-diol;methyl prop-2-enoate Chemical compound OCCO.COC(=O)C=C WCZHHZGITDJUQI-UHFFFAOYSA-N 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- PDZGAEAUKGKKDE-UHFFFAOYSA-N lithium;naphthalene Chemical compound [Li].C1=CC=CC2=CC=CC=C21 PDZGAEAUKGKKDE-UHFFFAOYSA-N 0.000 description 1
- 229920001427 mPEG Polymers 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 229960001708 magnesium carbonate Drugs 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- YACCECLVHQLZQK-UHFFFAOYSA-N methoxyperoxyethane Chemical compound CCOOOC YACCECLVHQLZQK-UHFFFAOYSA-N 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- IJJSYKQZFFGIEE-UHFFFAOYSA-N naphthalene;potassium Chemical compound [K].C1=CC=CC2=CC=CC=C21 IJJSYKQZFFGIEE-UHFFFAOYSA-N 0.000 description 1
- URXNVXOMQQCBHS-UHFFFAOYSA-N naphthalene;sodium Chemical compound [Na].C1=CC=CC2=CC=CC=C21 URXNVXOMQQCBHS-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/60—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in meta- or para- positions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/14—Thioxanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D335/16—Oxygen atoms, e.g. thioxanthones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F20/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/38—Esters containing sulfur
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C08F220/301—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one oxygen in the alcohol moiety
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C08F220/303—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one or more carboxylic moieties in the chain
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1339—Gaskets; Spacers; Sealing of cells
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/283—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(meth)acrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Mathematical Physics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Sealing Material Composition (AREA)
- Liquid Crystal (AREA)
- Polymerisation Methods In General (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
A purpose of the present invention is to provide a polymerizable monomer having low contamination with respect to liquid crystals, high sensitivity to light of long wavelengths, and an exceptional sensitizing effect, and a polymer compound obtained by polymerizing the polymerizable monomer. Another purpose of the present invention is to provide a photocurable resin composition containing the polymerizable monomer and/or the polymer compound; a sealing agent for liquid crystal display elements which uses the photocurable resin composition; and a vertical conduction material and liquid crystal display element which are manufactured using the sealing agent for liquid crystal display elements. The present invention is a polymerizable monomer obtained by causing a thioxanthone derivative that has a functional group capable of reacting with a dialkylaminobenzoic acid compound or epoxy group to react with an epoxy group having an unsaturated double bond or an epoxy group having an alkoxysilyl group.
Description
Technical field
The present invention relates to the pollution to liquid crystal low, to highly sensitive, the polymerizable monomer that sensitization effect is also excellent of the light of long wavelength and macromolecular compound that the polymerization of this polymerizable monomer is obtained. In addition, the present invention relates to containing this polymerizable monomer and/or the Photocurable resin composition of this macromolecular compound, the sealing material for liquid crystal display device using this Photocurable resin composition and make and the conductive material up and down using this sealing material for liquid crystal display device and manufacturing and liquid crystal display device.
Background technology
In recent years, as the manufacture method of the liquid crystal display device such as liquid crystal display, from shortening the beat time, use the viewpoint such as optimization of amount of liquid crystal to consider, it may also be useful to be as disclosed in patent documentation 1, patent documentation 2, employ the photo-thermal containing curable resin, Photoepolymerizationinitiater initiater and thermal curing agents and with the sealing agent of curing, the liquid crystal drop under type that is called as technique of dripping.
Dripping in technique, first, at 2 with a slice of the transparency carrier of electrode is formed rectangular seal pattern by divider. Then, the tiny droplets of liquid crystal dripping to when sealing agent does not solidify whole in the frame of transparency carrier, another transparency carrier overlapping, carries out temporary fixing to light such as sealing portion irradiation ultraviolet radiations immediately. Thereafter, carry out when liquid crystal is annealed heating and carrying out main solidification, make liquid crystal display device. If under reduced pressure carrying out the laminating of substrate, then can manufacturing liquid crystal display device with extreme efficiency, at present, this technique of dripping becomes the main flow of the manufacture method of liquid crystal display device.
In addition, universal present at the various mobile equipment with liquid crystal panel such as portable phone, portable game, the miniaturization of device is the problem wishing most to realize. As the method for the miniaturization of device, the narrow frame of liquid crystal display part can be enumerated, such as, under the position in sealing portion being configured in black matrix" (designing hereinafter also referred to narrow frame).
But, in narrow frame designs, sealing agent is configured in the underface of black matrix", if therefore carrying out dripping technique, then the light of the irradiation when making sealing agent carry out photocuring is covered, and there is the inside that light does not arrive sealing agent, and solidification becomes insufficient problem. If the solidification of sealing agent becomes insufficient like this, then there is the problem easily producing liquid crystal pollution in the sealing agent composition stripping to liquid crystal do not solidified.
In patent documentation 3, disclose and the Photoepolymerizationinitiater initiater of highly sensitive is engaged in sealing agent.But, if only coordinating the Photoepolymerizationinitiater initiater of highly sensitive, then cannot make the abundant photocuring of sealing agent. In addition, in patent documentation 4, disclose and the Photoepolymerizationinitiater initiater of highly sensitive and sensitizing agent combination are engaged in sealing agent. But, owing to using sensitizing agent, therefore there is the problem easily producing liquid crystal pollution.
Prior art literature
Patent documentation
Patent documentation 1: Japanese Unexamined Patent Publication 2001-133794 publication
Patent documentation 2: No. 02/092718th, International Publication
Patent documentation 3: No. 2011/002028th, International Publication
Patent documentation 4: Japanese Unexamined Patent Publication 2010-286640 publication
Summary of the invention
The problem that invention to be solved
It is an object of the present invention to provide the pollution to liquid crystal low, to highly sensitive, the polymerizable monomer that sensitization effect is also excellent of the light of long wavelength and macromolecular compound that the polymerization of this polymerizable monomer is obtained. In addition, it is an object of the present invention to provide containing this polymerizable monomer and/or the Photocurable resin composition of this macromolecular compound, the sealing material for liquid crystal display device using this Photocurable resin composition and make and the conductive material up and down using this sealing material for liquid crystal display device and manufacturing and liquid crystal display device.
For solving the means of problem
The present invention be make dialkyl amino yl benzoic acid based compound or have can with the thioxanthone derivates of the functional group of epoxy reaction and there is the epoxy compounds of unsaturated double-bond or there is the epoxy compounds reaction of alkoxysilyl and the polymerizable monomer that obtains.
The present invention is below described in detail.
The present inventor finds startledly, there is the polymerizable monomer of specific structure, by the polymerization of this polymerizable monomer, the macromolecular compound that obtains is low to the pollution of liquid crystal, to the light of long wavelength highly sensitive, sensitization effect is also excellent. Therefore, the present inventor finds, with the use of cooperation this polymerizable monomer, this macromolecular compound as the Photocurable resin composition of Photoepolymerizationinitiater initiater or sensitizing agent, such that it is able to obtain light solidified excellence and the sealing material for liquid crystal display device of liquid crystal pollution can be suppressed, thus complete the present invention.
The polymerizable monomer of the present invention make dialkyl amino yl benzoic acid based compound or have can with the thioxanthone derivates (being also simply called below " thioxanthone derivates ") of the functional group of epoxy reaction and have unsaturated double-bond epoxy compounds or have alkoxysilyl epoxy compounds (being also called in the lump below " epoxy compounds of the present invention ") reaction obtain.
As above-mentioned dialkyl amino yl benzoic acid based compound, include, for example: the compound shown in the compound shown in the compound shown in following formula (1-1), following formula (1-2), following formula (1-3), 7-(dimethylamino) coumarin-3-carboxylic acid etc. Wherein, compound shown in compound shown in preferred following formula (1-1), following formula (1-2) or the compound shown in following formula (1-3), it is more preferable to the compound shown in the compound shown in following formula (2-1), following formula (2-2) or the compound shown in following formula (2-3).
Above-mentioned thioxanthone derivates have can with the functional group of epoxy reaction.
As above-mentioned can with the functional group of epoxy reaction, include, for example hydroxyl, carboxyl, amino etc. Wherein, it is preferable that hydroxyl or carboxyl.
As above-mentioned thioxanthone derivates, include, for example: the compound shown in following formula (3), 2-amino-9H-thioxanthene-9-ketone etc.Wherein, it is preferable that the compound shown in following formula (3), it is more preferable to be the compound shown in following formula (5-1) or the compound shown in (5-2).
In formula (3), X is the group shown in hydrogen, hydroxyl or following formula (4). Each X can be the same or different, but at least one X is the group shown in hydroxyl or following formula (4).
It is there is the epoxy compounds of unsaturated double-bond or there is the epoxy compounds of alkoxysilyl with the epoxy compounds of the present invention of above-mentioned dialkyl amino yl benzoic acid based compound or the reaction of above-mentioned thioxanthone derivates.
Above-mentioned unsaturated double-bond or alkoxysilyl have the effect as the polymerizability reactive group involved by the polymerization of the polymerizable monomer of the present invention.
As the functional group with above-mentioned unsaturated double-bond, include, for example: (methyl) acryloxy, vinyl, allyl group etc. Wherein, it is preferable that (methyl) acryloxy.
It should be noted that, in this manual, above-mentioned " (methyl) acryloxy " refers to acryloxy or methacryloxypropyl base.
As above-mentioned alkoxysilyl, include, for example: trimethoxysilyl, triethoxysilyl, methyl dimethoxy oxygen base silyl, methyl diethoxy silyl etc. Wherein, it is preferable that trimethoxysilyl.
As the epoxy compounds of the present invention, it is preferred to use the compound shown in following formula (6-1) or (6-2).
In formula (6-1), R1Represent hydrogen or methyl. In formula (6-2), R2Represent carbon number be 1～10 alkyl or carbon number be the alkoxyl group of 1～10. Each R2Can be the same or different, but at least one R2For carbon number is the alkoxyl group of 1～10.
The method of the polymerizable monomer of the present invention is obtained as making the epoxy compounds of above-mentioned dialkyl amino yl benzoic acid based compound or above-mentioned thioxanthone derivates and the present invention react, can enumerate: under the existence of basic catalyst, make the epoxy compounds of above-mentioned dialkyl amino yl benzoic acid based compound or above-mentioned thioxanthone derivates and the present invention stir the method etc. of limit reaction in 6～72 hours below the condition of 80～130 DEG C.
From reactive viewpoint, the reaction of the epoxy compounds of above-mentioned dialkyl amino yl benzoic acid based compound or above-mentioned thioxanthone derivates and the present invention preferably carries out under the existence of trivalent organophosphorus acid compound and/or amine compound.
Above-mentioned dialkyl amino yl benzoic acid based compound when reacting as making the epoxy compounds of above-mentioned dialkyl amino yl benzoic acid based compound or above-mentioned thioxanthone derivates and the present invention or the use ratio of epoxy compounds of above-mentioned thioxanthone derivates and the present invention, with molar ratio computing, it is preferable to above-mentioned dialkyl amino yl benzoic acid based compound or above-mentioned thioxanthone derivates: epoxy compounds=1 of the present invention: 1～10: 1. By making the use ratio of the epoxy compounds of above-mentioned dialkyl amino yl benzoic acid based compound or above-mentioned thioxanthone derivates and the present invention be this scope such that it is able to have the polymerizable monomer of the present invention of photoreactive group with high receipts rate manufacture.
As the basic catalyst used when making the epoxy compounds of above-mentioned dialkyl amino yl benzoic acid based compound or above-mentioned thioxanthone derivates and the present invention react, include, for example: triphenylphosphine, triethylamine, tripropyl amine, Tetramethyl Ethylene Diamine, dimethyllaurylamine, triethyl benzyl ammonia chloride, trimethylammonium hexadecyl brometo de amonio, Tetrabutyl amonium bromide, trimethyl butyl bromo-phosphonium, tetrabutyl phosphonium bromide phosphorus etc.Wherein, it is preferable that triphenylphosphine.
In addition, above-mentioned basic catalyst can also be carried on a shoulder pole and be loaded in polymkeric substance and be used as Polymer Supported basic catalyst.
As the polymerizable monomer (hereinafter also referred to " being derived from the polymerizable monomer of dialkyl amino yl benzoic acid based compound ") of the present invention making the epoxy compounds of above-mentioned dialkyl amino yl benzoic acid based compound and the present invention react and obtain, specifically include, for example the compound etc. shown in following formula (7-1)～(7-6).
In formula (7-1)～(7-3), R1Represent hydrogen or methyl. In formula (7-4)～(7-6), R2Represent carbon number be 1～10 alkyl or carbon number be the alkoxyl group of 1～10. Each R2Can be the same or different, but at least one R2For carbon number is the alkoxyl group of 1～10.
As the polymerizable monomer (hereinafter also referred to " being derived from the polymerizable monomer of thioxanthone derivates ") of the present invention making the epoxy compounds of above-mentioned thioxanthone derivates and the present invention react and obtain, specifically include, for example the compound etc. shown in following formula (8-1)～(8-4).
In formula (8-1), (8-2), R1Represent hydrogen or methyl. In formula (8-3), (8-4), R2Represent carbon number be 1～10 alkyl or carbon number be the alkoxyl group of 1～10. Each R2Can be the same or different, but at least one R2For carbon number is the alkoxyl group of 1～10.
The macromolecular compound (hereinafter also referred to " macromolecular compound of the present invention ") polymerization of the polymerizable monomer of the present invention obtained also is one of the present invention.
As the method by the polymerizable monomer polymerization being derived from dialkyl amino yl benzoic acid based compound above-mentioned among the polymerizable monomer of the present invention, include, for example cationoid polymerisation, anionoid polymerization, radical polymerization etc. Wherein, it is preferable that make the compound dissolved in toluene solvant stir the method for limit reaction in 4～12 hours under the existence of the radical polymerization initiators such as Diisopropyl azodicarboxylate in the condition limit of 60～100 DEG C.
As the cationic polymerisation catalyst of use when the above-mentioned polymerizable monomer being derived from dialkyl amino yl benzoic acid based compound is carried out cationoid polymerisation, include, for example: the sulfonic acid etc. such as the carboxylic acids such as the mineral acids such as hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, methanesulfonic, ethane sulfonic acid, Phenylsulfonic acid, tosic acid. Wherein, it is preferable that hydrochloric acid.
As the anionic polymerization catalyst of use when the above-mentioned polymerizable monomer being derived from dialkyl amino yl benzoic acid based compound is carried out anionoid polymerization, include, for example: n-Butyl Lithium, s-butyl lithium, the lithium alkylides such as tert-butyl lithium, 1, 4-bis-lithium butane (1, 4-ジ リ チ オ Block タ Application) etc. alkylidene group two lithium (ア Le キ レ Application ジ リ チ ウ system), phenyl lithium, lithium, lithium naphthalene, sodium naphthalene, potassium naphthalene, normal-butyl magnesium, just own base magnesium, calcium ethylate, calcium stearate, trimethyl carbinol strontium, barium ethylate, barium isopropylate, sulfur alcohol barium, trimethyl carbinol barium, barium phenolate, diethylin barium, barium stearate etc. wherein, it is preferable that n-Butyl Lithium.
As the radical polymerization initiator of use when the above-mentioned polymerizable monomer being derived from dialkyl amino yl benzoic acid based compound is carried out radical polymerization, include, for example: Diisopropyl azodicarboxylate, azo two cyclohexanenitrile, azo two (2,4-methyl pentane nitrile) etc. Azo, benzoyl peroxide, lauroyl peroxide, adjacent chlorine benzoyl peroxide, O-methoxy benzoyl peroxide, peroxidation 3, the organo-peroxides etc. such as 5,5-trimethyl acetyl, the peroxidation 2 ethyl hexanoic acid tert-butyl ester, ditertiary butyl peroxide.Wherein, it is preferable that Diisopropyl azodicarboxylate.
As the method by the polymerizable monomer polymerization being derived from thioxanthone derivates above-mentioned among the polymerizable monomer of the present invention, include, for example: the polymerization etc. utilizing the sol-gel method under the existence of an acidic catalyst or basic catalyst, but it is preferably and the polymerizable monomer of the present invention being dissolved in alcohol solvent is mixed with water, under an acidic catalyst, stir the method for limit reaction in 2～24 hours in the condition limit of 60～120 DEG C.
As an acidic catalyst used when the above-mentioned polymerizable monomer being derived from thioxanthone derivates is polymerized, include, for example: the sulfonic acid etc. such as the carboxylic acids such as the mineral acids such as hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, methanesulfonic, ethane sulfonic acid, Phenylsulfonic acid, tosic acid. Wherein, it is preferable that hydrochloric acid.
As the basic catalyst used when being polymerized by the above-mentioned polymerizable monomer being derived from thioxanthone derivates, the organic compound such as mineral compound, amine compound etc. such as sodium hydroxide, potassium hydroxide, ammonia can be enumerated. Wherein, it is preferable that sodium hydroxide.
The preferred lower limit of the polymerization degree of the macromolecular compound of the present invention is 3. The polymerization degree of the macromolecular compound of the present invention is 2, when being dipolymer, when as Photoepolymerizationinitiater initiater or sensitizing agent for sealing material for liquid crystal display device, sometimes can not fully suppress liquid crystal pollution. The preferred lower limit of the polymerization degree of the macromolecular compound of the present invention is 10.
In addition, the preferred upper limit of the polymerization degree of the macromolecular compound of the present invention is 1000. When the polymerization degree of the macromolecular compound of the present invention is greater than 1000, when as Photoepolymerizationinitiater initiater or sensitizing agent for sealing material for liquid crystal display device, coating is deteriorated sometimes. The preferred upper limit of the polymerization degree of the macromolecular compound of the present invention is 100.
The preferred lower limit of the number-average molecular weight of the macromolecular compound of the present invention is 2000, the preferred upper limit is 30,000. When the number-average molecular weight of the macromolecular compound of the present invention is less than 2000, when as Photoepolymerizationinitiater initiater or sensitizing agent for sealing material for liquid crystal display device, sometimes can not fully suppress liquid crystal pollution. When the number-average molecular weight of the macromolecular compound of the present invention is greater than 30,000, when as Photoepolymerizationinitiater initiater or sensitizing agent for sealing material for liquid crystal display device, coating is deteriorated sometimes. The preferred lower limit of the number-average molecular weight of the macromolecular compound of the present invention is 5000, the preferred upper limit is 10,000.
It should be noted that, in this manual, above-mentioned number-average molecular weight utilizes gel permeation chromatography (GPC) to carry out measuring and the value obtained by polystyrene conversion. Measure based on the post during number-average molecular weight of polystyrene conversion as by GPC, include, for example ShodexLF-804 (Showa electrician company manufacture) etc.
The macromolecular compound of the present invention to the light of long wavelength highly sensitive, sensitization effect is also excellent, it is preferred to be used as Photoepolymerizationinitiater initiater or sensitizing agent.
Also it is one of the present invention containing the Photocurable resin composition of curable resin and the polymerizable monomer of the present invention and/or the macromolecular compound of the present invention.
From the view point of just do not react with curable resin after the upper coatings such as substrate and prevent liquid crystal pollution, the Photocurable resin composition of the present invention preferably contains the macromolecular compound of the present invention. The macromolecular compound of the present invention has the effect as Photoepolymerizationinitiater initiater or sensitizing agent.
The content of the macromolecular compound of the present invention in Photocurable resin composition for the present invention, relative to curable resin 100 weight part, it is preferable that lower limit be 0.5 weight part, it is preferable that the upper limit be 20 weight parts.If the content of the macromolecular compound of the present invention is less than 0.5 weight part, then the light solidified of the Photocurable resin composition obtained is deteriorated sometimes. When the content of the macromolecular compound of the present invention is greater than 20 weight part, the Photocurable resin composition obtained sometimes weathering resistance, preserve bad stability, or for during sealing material for liquid crystal display device produce liquid crystal pollution. The preferred lower limit of the content of the macromolecular compound of the present invention is 2 weight parts, the preferred upper limit is 10 weight parts.
The Photocurable resin composition preferably combination of the present invention contains the macromolecular compound (hereinafter also referred to " being derived from the macromolecular compound of dialkyl amino yl benzoic acid based compound ") of the present invention being polymerized and obtain by the above-mentioned polymerizable monomer being derived from dialkyl amino yl benzoic acid based compound, with both macromolecular compounds (hereinafter also referred to " being derived from the macromolecular compound of thioxanthone derivates ") of the present invention that the above-mentioned polymerizable monomer being derived from thioxanthone derivates is polymerized and obtain, more preferably use the above-mentioned macromolecular compound being derived from dialkyl amino yl benzoic acid based compound as Photoepolymerizationinitiater initiater, and use the above-mentioned macromolecular compound being derived from thioxanthone derivates as sensitizing agent.
Macromolecular compound that in the Photocurable resin composition of the present invention, combination is derived from dialkyl amino yl benzoic acid based compound containing above-mentioned and above-mentioned be derived from thioxanthone derivates both macromolecular compounds when, above-mentioned it is derived from the macromolecular compound of dialkyl amino yl benzoic acid based compound and the content ratio of the above-mentioned macromolecular compound being derived from thioxanthone derivates, with mass ratio range, it is preferable to be derived from the macromolecular compound of dialkyl amino yl benzoic acid based compound: macromolecular compound=1 being derived from thioxanthone derivates: 1～5: 1. It is this scope by making to be derived from the macromolecular compound of dialkyl amino yl benzoic acid based compound with the content ratio of the macromolecular compound being derived from thioxanthone derivates, thus the light solidified making the light utilizing long wavelength of the Photocurable resin composition obtained becomes excellent especially.
In the Photocurable resin composition of the present invention except the macromolecular compound of the present invention, other Photoepolymerizationinitiater initiater, other sensitizing agent can also be contained in the dysgenic scopes such as liquid crystal pollution for not causing during sealing material for liquid crystal display device.
As other Photoepolymerizationinitiater initiater above-mentioned, include, for example: the compound etc. shown in the compound shown in benzophenone based compound, methyl phenyl ketone based compound, acylphosphine oxide based compound, two luxuriant titanium sub-group compounds, oxime ester based compound, benzoin ether based compound, benzil, thioxanthone, following formula (9-1), following formula (9-2).
As the commercially available product among other Photoepolymerizationinitiater initiater above-mentioned, include, for example: IRGACURE184, IRGACURE369, IRGACURE379, IRGACURE651, IRGACURE819, IRGACURE907, IRGACURE2959, IRGACUREOXE01, LucirinTPO (is BASF company to manufacture), benzoin methylether, ethoxybenzoin, benzoin iso-propylether (is Tokyo chemical conversion industrial to manufacture), ADEKAOPTMERN-1414, ADEKAOPTMERN-1717, ADEKAOPTMERN-1919, ADEKAOPTMERNCI-839, ADEKAOPTMERNCI-930 etc. (are ADEKA company to manufacture).
As other sensitizing agent above-mentioned, include, for example: the compound etc. shown in the compound shown in anthracene derivant, anthraquinone derivative, coumarin derivatives, thioxanthone derivates, phthalocyanine derivates, following formula (10-1), following formula (10-2).
As above-mentioned anthracene derivant, include, for example: 9,10-dibutoxy anthracene, 9,10-bis-propoxy-anthracene quinone, 9,10-oxyethyl group anthracene quinone etc.
As above-mentioned anthraquinone derivative, include, for example: 2-ethyl-anthraquinone, 1-methylanthracene quinone, 1,4-dihydroxyanthraquinone, 2-(2-hydroxyl-oxethyl)-anthracene quinone etc.
As above-mentioned coumarin derivatives, include, for example 7-diethylin-4-methylcoumarin etc.
As above-mentioned thioxanthone derivates, include, for example 2,4-diethyl thioxanthone, CTX, ITX, the chloro-4-propyl group thioxanthone of 1-etc.
As above-mentioned phthalocyanine derivates, include, for example phthalocyanine etc.
In addition, it is possible to the benzophenone based compound enumerated as other Photoepolymerizationinitiater initiater above-mentioned is used as other sensitizing agent above-mentioned.
The Photocurable resin composition of the present invention contains curable resin.
Above-mentioned curable resin is preferably containing (methyl) acrylic resin.
From the aspect that reactivity is high, above-mentioned (methyl) acrylic resin preferably has 2～3 (methyl) acryloxies in the molecule.
As above-mentioned (methyl) acrylic resin, include, for example: the ester cpds that the compound with hydroxyl is reacted with (methyl) vinylformic acid and obtain, ring oxygen (methyl) acrylate making (methyl) vinylformic acid and epoxy compounds react and obtain, carbamate (methyl) acrylate etc. making (methyl) acrylic acid derivative with hydroxyl and isocyanate compound react and obtain. Wherein, it is preferable that ring oxygen (methyl) acrylate.
It should be noted that, in this manual, above-mentioned " (methyl) vinylformic acid " refers to acrylic or methacrylic acid, and above-mentioned " (methyl) acrylic resin " refers to the resin with (methyl) acryloxy. In addition, above-mentioned " (methyl) acrylate " acrylate or methacrylic ester is referred to. In addition, above-mentioned " ring oxygen (methyl) acrylate " expression makes the compound that the whole epoxy group(ing) in epoxy resin is reacted and obtain with (methyl) vinylformic acid.
As the simple function ester cpds among above-mentioned ester cpds, include, for example: (methyl) vinylformic acid 2-hydroxy methacrylate, (methyl) vinylformic acid 2-hydroxy propyl ester, (methyl) vinylformic acid 4-hydroxybutyl, (methyl) vinylformic acid 2-hydroxybutyl, (methyl) isobutyl acrylate, (methyl) tert-butyl acrylate, (methyl) Isooctyl acrylate monomer, (methyl) lauryl acrylate, (methyl) stearyl acrylate ester, (methyl) isobornyl acrylate, (methyl) cyclohexyl acrylate, (methyl) vinylformic acid 2-methoxyl group second ester, methoxyl group ethylene glycol (methyl) acrylate, (methyl) vinylformic acid 2-ethoxy ethyl ester, (methyl) tetrahydrofurfuryl acrylate, (methyl) benzyl acrylate, ethyl carbitol (methyl) acrylate, (methyl) vinylformic acid phenoxy ethyl, phenoxy group Diethylene Glycol (methyl) acrylate, phenoxy group polyoxyethylene glycol (methyl) acrylate, methoxy poly (ethylene glycol) (methyl) acrylate, (methyl) vinylformic acid-2,2,2-trifluoro ethyl ester, (methyl) vinylformic acid 2,2,3,3-tetra-fluorine propyl ester, (methyl) vinylformic acid 1H, 1H, 5H-eight fluorine pentyl ester, imide (methyl) acrylate, (methyl) methyl acrylate, (methyl) ethyl propenoate, (methyl) n-butyl acrylate, (methyl) propyl acrylate, (methyl) ethyl acrylate, (methyl) vinylformic acid n-octyl, (methyl) vinylformic acid ester in the different ninth of the ten Heavenly Stems, the different Semen Myristicae ester of (methyl) vinylformic acid, (methyl) vinylformic acid 2-butoxy second ester, (methyl) vinylformic acid 2-phenoxy ethyl, (methyl) vinylformic acid dicyclopentenyloxyethyl methacrylate, (methyl) isodecyl acrylate, (methyl) diethylaminoethyl acrylate, (methyl) dimethylaminoethyl acrylate, 2-(methyl) acryloxy ethylsuccinic acid, 2-(methyl) acryloxy ethyl hexahydrophthalic acid, 2-(methyl) acryloxy ethyl 2-hydroxypropyl phthalate, (methyl) glycidyl acrylate, 2-(methyl) acryloxy ethyl phosphoric acid ester etc.
In addition, as two sense ester cpds among above-mentioned ester cpds, include, for example: 1,4-butyleneglycol two (methyl) acrylate, 1,3 butylene glycol two (methyl) acrylate, 1,6-hexylene glycol two (methyl) acrylate, 1,9-nonanediol two (methyl) acrylate, 1,10-decanediol two (methyl) acrylate, 2-normal-butyl-2-ethyl-1,3-propylene glycol two (methyl) acrylate, dipropylene glycol two (methyl) acrylate, tripropylene glycol two (methyl) acrylate, polypropylene glycol (methyl) acrylate, ethylene glycol bisthioglycolate (methyl) acrylate, Diethylene Glycol two (methyl) acrylate, four ethylene glycol bisthioglycolates (methyl) acrylate, polyoxyethylene glycol two (methyl) acrylate, propylene oxide addition dihydroxyphenyl propane two (methyl) acrylate, ethyleneoxide addition dihydroxyphenyl propane two (methyl) acrylate, ethyleneoxide addition Bisphenol F two (methyl) acrylate, dihydroxymethyl dicyclopentadienyl two (methyl) acrylate, neopentyl glycol two (methyl) acrylate, oxyethane modification isocyanuric acid two (methyl) acrylate, (methyl) vinylformic acid 2-hydroxyl-3-(methyl) acryloxy propyl ester, carbonate diol two (methyl) acrylate, polyether glycol two (methyl) acrylate, polyester glycol two (methyl) acrylate, polycaprolactone glycol two (methyl) acrylate, polybutadiene diol two (methyl) acrylate etc.
In addition, as ester cpds more than three senses among above-mentioned ester cpds, include, for example: tetramethylolmethane three (methyl) acrylate, trimethylolpropane tris (methyl) acrylate, propylene oxide addition trimethylolpropane tris (methyl) acrylate, ethyleneoxide addition trimethylolpropane tris (methyl) acrylate, caprolactone modification trimethylolpropane tris (methyl) acrylate, ethyleneoxide addition isocyanuric acid three (methyl) acrylate, Dipentaerythritol five (methyl) acrylate, Dipentaerythritol six (methyl) acrylate, ditrimethylolpropane four (methyl) acrylate, tetramethylolmethane four (methyl) acrylate, glycerol three (methyl) acrylate, propylene oxide addition glycerol three (methyl) acrylate, three (methyl) acrylyl oxy-ethyl phosphoric acid ester etc.
As above-mentioned ring oxygen (methyl) acrylate, include, for example: ring oxygen (methyl) acrylate etc. carrying out reacting under the existence of basic catalyst and obtain by epoxy resin and (methyl) vinylformic acid according to ordinary method.
For the epoxy resin as the raw material for the synthesis of above-mentioned ring oxygen (methyl) acrylate, include, for example: bisphenol A type epoxy resin, bisphenol f type epoxy resin, bisphenol-s epoxy resin, 2, 2 '-diallyl bisphenol type epoxy resin, A Hydrogenated Bisphenol A type epoxy resin, propylene oxide addition bisphenol A type epoxy resin, Resorcinol type epoxy resin, biphenyl type epoxy resin, thioether-type epoxy resin, phenylbenzene ether type epoxy, dicyclopentadiene type epoxy resin, naphthalene type epoxy resin, phenol novolak type epoxy resin, o-cresol phenolic epoxy varnish, dicyclopentadiene phenolic varnish type epoxy resin, biphenyl phenolic resin varnish type epoxy resin, naphthol novolac type epoxy resin, glycidyl amine type epoxy resin, alkyl polyols type epoxy resin, modified rubber type epoxy resin, epihydric alcohol ester compound etc.
As the commercially available product among above-mentioned bisphenol A type epoxy resin, include, for example: jER828EL, jER1004 (be Mitsubishi Chemical Ind manufacture), EPICLON850 (manufacture of DIC company) etc.
As the commercially available product among above-mentioned bisphenol f type epoxy resin, include, for example: jER806, jER4004 (are Mitsubishi Chemical Ind to manufacture).
As the commercially available product among above-mentioned bisphenol-s epoxy resin, include, for example: EPICLONEXA1514 (manufacture of DIC company) etc.
As the commercially available product among above-mentioned 2,2 '-diallyl bisphenol type epoxy resin, include, for example: RE-810NM (chemical drug company of Japan manufactures) etc.
As the commercially available product among above-mentioned A Hydrogenated Bisphenol A type epoxy resin, include, for example EPICLONEXA7015 (manufacture of DIC company) etc.
As the commercially available product among above-mentioned propylene oxide addition bisphenol A type epoxy resin, include, for example EP-4000S (manufacture of ADEKA company) etc.
As the commercially available product among above-mentioned Resorcinol type epoxy resin, include, for example EX-201 (manufacture of NagaseChemtex company) etc.
As the commercially available product among above-mentioned biphenyl type epoxy resin, include, for example jERYX-4000H (Mitsubishi Chemical Ind's manufacture) etc.
As the commercially available product among above-mentioned sulfide type epoxy resin, include, for example YSLV-50TE (Nippon Steel lives aurification company and manufactures) etc.
As the commercially available product among above-mentioned phenylbenzene ether type epoxy, include, for example YSLV-80DE (Nippon Steel lives aurification company and manufactures) etc.
As the commercially available product among above-mentioned dicyclopentadiene type epoxy resin, include, for example EP-4088S (manufacture of ADEKA company) etc.
As the commercially available product among above-mentioned naphthalene type epoxy resin, include, for example: EPICLONHP4032, EPICLONEXA-4700 (are DIC company to manufacture).
As the commercially available product among above-mentioned phenol novolak type epoxy resin, include, for example EPICLONN-770 (manufacture of DIC company) etc.
As the commercially available product among above-mentioned o-cresol phenolic epoxy varnish, include, for example EPICLONN-670-EXP-S (manufacture of DIC company) etc.
As the commercially available product among above-mentioned dicyclopentadiene phenolic varnish type epoxy resin, include, for example EPICLONHP7200 (manufacture of DIC company) etc.
As the commercially available product among above-mentioned biphenyl phenolic resin varnish type epoxy resin, include, for example NC-3000P (chemical drug company of Japan manufactures) etc.
As the commercially available product among above-mentioned naphthol novolac type epoxy resin, include, for example ESN-165S (Nippon Steel lives aurification company and manufactures) etc.
As the commercially available product among above-mentioned glycidyl amine type epoxy resin, include, for example: jER630 (Mitsubishi Chemical Ind's manufacture), EPICLON430 (manufacture of DIC company), TETRAD-X (manufacture of Mitsubishi Gas Chemical company) etc.
As the commercially available product among abovementioned alkyl polyvalent alcohol type epoxy resin, include, for example: ZX-1542 (Nippon Steel lives aurification company and manufactures), EPICLON726 (manufacture of DIC company), EPOLIGHT80MFA (chemistry company of common prosperity society manufactures), DenacolEX-611 (manufacture of NagaseChemtex company) etc.
As the commercially available product among above-mentioned modified rubber type epoxy resin, include, for example: YR-450, YR-207 (be Nippon Steel live aurification company manufacture), EPOLEADPB (manufacture of Daicel company) etc.
As the commercially available product among above-mentioned epihydric alcohol ester compound, include, for example DenacolEX-147 (manufacture of NagaseChemtex company) etc.
As other commercially available product among above-mentioned epoxy resin, include, for example: YDC-1312, YSLV-80XY, YSLV-90CR (be Nippon Steel live aurification company manufacture), XAC4151 (manufacture of company of Asahi Chemical Industry), jER1031, jER1032 (being Mitsubishi Chemical Ind's manufacture), EXA-7120 (manufacture of DIC company), TEPIC (manufacture of Nissan Chemical company) etc.
As the method manufacturing above-mentioned ring oxygen (methyl) acrylate, concrete example as: Resorcinol type epoxy resin (NagaseChemtex Inc., " EX-201 ") 360 weight parts, p methoxy phenol 2 weight part as stopper, triethylamine 2 weight part as catalysts and vinylformic acid 210 weight part are sent into air and are carried out return stirring, while reacting 5 hours at 90 DEG C, Resorcinol type epoxy acrylate thus can be obtained.
As the commercially available product among above-mentioned ring oxygen (methyl) acrylate, include, for example: EBECRYL860, EBECRYL3200, EBECRYL3201, EBECRYL3412, EBECRYL3600, EBECRYL3700, EBECRYL3701, EBECRYL3702, EBECRYL3703, EBECRYL3800, EBECRYL6040, EBECRYLRDX63182 (is Daicel-Allnex company to manufacture), EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020 (is chemical industry company of Xin Zhong village to manufacture), EPOXYESTERM-600A, EPOXYESTER40EM, EPOXYESTER70PA, EPOXYESTER200PA, EPOXYESTER80MFA, EPOXYESTER3002M, EPOXYESTER3002A, EPOXYESTER1600A, EPOXYESTER3000M, EPOXYESTER3000A, EPOXYESTER200EA, EPOXYESTER400EA (is chemistry company of common prosperity society to manufacture), DenacolAcrylateDA-141, DenacolAcrylateDA-314, DenacolAcrylateDA-911 (is NagaseChemtex company to manufacture).
As above-mentioned carbamate (methyl) acrylate making (methyl) acrylic acid derivative with hydroxyl and isocyanate compound react and obtain, such as can obtain as follows: relative to isocyanate compound 1 equivalent with two isocyanate group, (methyl) acrylic acid derivative 2 equivalent with hydroxyl is reacted with it and obtain under the tin based compound of catalytic amount exists.
With regard to the isocyanate compound of the raw material as above-mentioned carbamate (methyl) acrylate, include, for example: isophorone diisocyanate, 2, 4-tolylene diisocyanate, 2, 6-tolylene diisocyanate, hexamethylene diisocyanate, trimethyl hexamethylene diisocyanate, ditan-4, 4 '-vulcabond (MDI), hydrogenation MDI, polymeric MDI, 1, 5-naphthalene diisocyanate, norbornene alkyl diisocyanate, ditolyl vulcabond, xylylene diisocyanate (XDI), hydrogenation XDI, lysinediisocyanate, triphenylmethane triisocyanate, three (isocyanic ester phenyl) thiophosphatephosphorothioate, tetramethylxylene diisocyanate, 1, 6, 11-undecane triisocyanate etc.
In addition, with regard to the isocyanate compound of the raw material as above-mentioned carbamate (methyl) acrylate, such as, can also use the reaction by the polyvalent alcohols such as ethylene glycol, glycerol, Sorbitol Powder, TriMethylolPropane(TMP), (gathering) propylene glycol, carbonate diol, polyether glycol, polyester glycol, polycaprolactone glycol and excessive isocyanate compound and the isocyanate compound of the chain growth that obtains.
With regard to (methyl) acrylic acid derivative with hydroxyl as the raw material of above-mentioned carbamate (methyl) acrylate, include, for example: (methyl) acrylic acid hydroxy alkyl esters such as (methyl) vinylformic acid 2-hydroxy methacrylate, (methyl) vinylformic acid 2-hydroxy propyl ester, (methyl) vinylformic acid 4-hydroxybutyl, (methyl) vinylformic acid 2-hydroxybutyl;List (methyl) acrylate of the dibasic alcohol such as ethylene glycol, propylene glycol, 1,3-propylene glycol, 1,3 butylene glycol, 1,4-butyleneglycol, polyoxyethylene glycol; List (methyl) acrylate of the trivalent alcohols such as trimethylolethane, TriMethylolPropane(TMP), glycerol or two (methyl) acrylate; Ring oxygen (methyl) acrylate etc. such as bisphenol-a epoxy acrylate.
Above-mentioned carbamate (methyl) acrylate concrete example is as obtained as follows: add TriMethylolPropane(TMP) 134 weight part, the BHT0.2 weight part as stopper, dibutyl tin laurate 0.01 weight part as catalysts, isophorone diisocyanate 666 weight part, while react 2 hours on 60 DEG C of return stirring limits, then, add 2-Hydroxy ethyl acrylate 51 weight part, air is sent into and return stirring in limit, while react 2 hours at 90C, thus obtain.
As the commercially available product among above-mentioned carbamate (methyl) acrylate, include, for example: M-1100, M-1200, M-1210, M-1600 (is East Asia synthesis company to manufacture), EBECRYL230, EBECRYL270, EBECRYL4858, EBECRYL8402, EBECRYL8804, EBECRYL8803, EBECRYL8807, EBECRYL9260, EBECRYL1290, EBECRYL5129, EBECRYL4842, EBECRYL210, EBECRYL4827, EBECRYL6700, EBECRYL220, EBECRYL2220 (is Daicel-Allnex company to manufacture), ArtresinUN-9000H, ArtresinUN-9000A, ArtresinUN-7100, ArtresinUN-1255, ArtresinUN-330, ArtresinUN-3320HB, ArtresinUN-1200TPK, ArtresinSH-500B (is Gen Shang industrial to manufacture), U-122P, U-108A, U-340P, U-4HA, U-6HA, U-324A, U-15HA, UA-5201P, UA-W2A, U-1084A, U-6LPA, U-2HA, U-2PHA, UA-4100, UA-7100, UA-4200, UA-4400, UA-340P, U-3HA, UA-7200, U-2061BA, U-10H, U-122A, U-340A, U-108, U-6H, UA-4000 (is chemical industry company of Xin Zhong village to manufacture), AH-600, AT-600, UA-306H, AI-600, UA-101T, UA-101I, UA-306T, UA-306I (is chemistry company of common prosperity society to manufacture).
For the object of the cementability improving the Photocurable resin composition obtained, above-mentioned curable resin is preferably also containing epoxy resin. As above-mentioned epoxy resin, include, for example: as epoxy resin, partly (methyl) acrylic modified epoxy resin etc. of the raw material for the synthesis of above-mentioned ring oxygen (methyl) acrylate.
It should be noted that; in this manual; above-mentioned part (methyl) acrylic modified epoxy resin refers to the resin in 1 molecule with epoxy group(ing) and each more than 1 of (methyl) acryl; such as, it is possible to reacted with (methyl) vinylformic acid and obtain by the epoxy group(ing) of a part for the epoxy resin making more than 2.
When the Photocurable resin composition of the present invention contains above-mentioned (methyl) acrylic resin and above-mentioned epoxy resin, it is preferable that the mode taking the ratio of (methyl) acryloxy and epoxy group(ing) as 50: 50～95: 5 coordinates above-mentioned (methyl) acrylic resin and above-mentioned epoxy resin. If the ratio of (methyl) acryloxy is less than 50%, even if then polymerization terminates, the epoxy resin composition that still a large amount of existence is not solidified, therefore for sometimes producing liquid crystal pollution during sealing material for liquid crystal display device. If the ratio of (methyl) acryloxy is greater than 95%, then the Photocurable resin composition obtained is cementability variation sometimes.
From the viewpoint of suppress liquid crystal pollution when being used for sealing material for liquid crystal display device, above-mentioned curable resin preferably has-OH base ,-NH-base ,-NH2The unit of the hydrogen bonds such as base.
The Photocurable resin composition of the present invention can also contain hot radical polymerization starter.
As above-mentioned hot radical polymerization starter, include, for example the hot radical polymerization starter being made up of azo-compound, organo-peroxide etc. Wherein, it is preferable to the initiator (hereinafter also referred to " polymeric azo initiator ") being made up of polymeric azo compound.
It should be noted that, in this manual, polymeric azo initiator refers to, have azo-group and by heat and produce (methyl) acryloxy can be made to solidify free radical, number-average molecular weight be the compound of more than 300.
The preferred lower limit of the number-average molecular weight of above-mentioned polymeric azo initiator is 1000, preferred upper limit is 300,000. If the number-average molecular weight of above-mentioned polymeric azo initiator is less than 1000, then sometimes liquid crystal being caused detrimentally affect for polymeric azo initiator during sealing material for liquid crystal display device. If the number-average molecular weight of above-mentioned polymeric azo initiator is greater than 300,000, then sometimes it is difficult to be mixed in curable resin. More preferably the lower limit of the number-average molecular weight of above-mentioned polymeric azo initiator is 5000, it is more preferable to the upper limit is 100,000, and preferred lower limit is 10,000 further, and the preferred upper limit is 90,000 further.
As above-mentioned polymeric azo initiator, include, for example: the polymeric azo initiator with the structure being bonded with the unit such as multiple polyalkylene oxide, polydimethylsiloxane by azo-group.
As the above-mentioned polymeric azo initiator with the structure being bonded with the unit such as multiple polyalkylene oxides by azo-group, it is preferable to have the polymeric azo initiator of polyethylene oxide structure. As such polymeric azo initiator, include, for example: 4, the polycondensate, 4 of 4 '-azo two (4-cyanopentanoic acid) and polyalkylene glycol, the polycondensate etc. of 4 '-azo two (4-cyanopentanoic acid) and the polydimethylsiloxane with terminal amino group, specifically, include, for example: VPE-0201, VPE-0401, VPE-0601, VPS-0501, VPS-1001 (the pure pharmaceutical worker industry company with light that is manufactures) etc.
In addition, as the azo-compound of non-polymer, include, for example: V-65, V-501 (the pure pharmaceutical worker industry company with light that is manufactures) etc.
As above-mentioned organo-peroxide, include, for example: ketone peroxide, ketal peroxide, hydrogen peroxide, dialkyl peroxide, peroxyester, peroxidation two acyl, peroxy dicarbonate etc.
About the content of above-mentioned hot radical polymerization starter, relative to curable resin 100 weight part, it is preferable that lower limit be 0.1 weight part, it is preferable that the upper limit be 30 weight parts. If the content of above-mentioned hot radical polymerization starter is less than 0.1 weight part, then the thermopolymerization of the Photocurable resin composition sometimes obtained can not fully carry out. If the content of above-mentioned hot radical polymerization starter is greater than 30 weight parts, then for sometimes producing liquid crystal pollution because of unreacted hot radical polymerization starter during sealing material for liquid crystal display device. More preferably the lower limit of the content of above-mentioned hot radical polymerization starter is 0.5 weight part, it is more preferable to the upper limit is 10 weight parts.
The Photocurable resin composition of the present invention can also contain thermal curing agents.
As above-mentioned thermal curing agents, include, for example: organic acid hydrazides, imdazole derivatives, amine compound, polyphenol based compound, acid anhydrides etc.Wherein, it is preferred to use organic acid hydrazides.
As above-mentioned organic acid hydrazides, include, for example: sebacoyl hydrazine, isopthalic dihydrazide, adipic dihydrazide, malonyl-hydrazine etc.
As the commercially available product among above-mentioned organic acid hydrazides, include, for example: SDH, ADH (are big chemistry company to manufacture), AMICUREVDH, AMICUREVDH-J, AMICUREUDH (being AjinomotoFine-Techno company to manufacture) etc.
About the content of above-mentioned thermal curing agents, relative to above-mentioned curable resin 100 weight part, it is preferable that lower limit is 1 weight part, preferred upper limit is 50 weight parts. If the content of above-mentioned thermal curing agents is less than 1 weight part, then Photocurable resin composition fully the thermofixation that sometimes cannot make to obtain. If the content of above-mentioned thermal curing agents is greater than 50 weight parts, then the viscosity of the Photocurable resin composition obtained becomes too high, and coating is deteriorated sometimes. The preferred upper limit of the content of above-mentioned thermal curing agents is 30 weight parts.
The objects such as the raising of the improvement of the raising for viscosity, the cementability based on stress dispersion effect, the improvement of linear expansivity, the wet fastness of cured article, the Photocurable resin composition of the present invention is preferably containing weighting agent.
As above-mentioned weighting agent, include, for example: the organic fillers such as the inorganic filler such as talcum, asbestos, silicon-dioxide, diatomite, terre verte, wilkinite, calcium carbonate, magnesiumcarbonate, aluminum oxide, montmorillonite, zinc oxide, acidifying iron, magnesium oxide, stannic oxide, titanium dioxide, magnesium hydroxide, aluminium hydroxide, glass microballon, silicon nitride, barium sulfate, gypsum, Calucium Silicate powder, sericite, atlapulgite, aluminium nitride, polyester micropartical, polyurethane particulate, vinyl polymer particulate, acrylic acid polymer particulate. These weighting agents can be used alone, it is also possible to and with two or more.
The preferred lower limit of the content of the above-mentioned weighting agent in Photocurable resin composition 100 weight part of the present invention is 10 weight parts, it is preferable that the upper limit is 70 weight parts. If the content of above-mentioned weighting agent is less than 10 weight parts, then the effect such as improvement that sometimes cannot give full play to cementability. If the content of above-mentioned weighting agent is greater than 70 weight parts, then the viscosity of the Photocurable resin composition obtained becomes too high, and coating is deteriorated sometimes. The preferred lower limit of the content of above-mentioned weighting agent is 20 weight parts, it is more preferable to the upper limit be 60 weight parts.
The Photocurable resin composition of the present invention is preferably containing silane coupling agent. Above-mentioned silane coupling agent mainly has as by the effect of the Photocurable resin composition of the present invention with the bonding auxiliary agent of the good bonding such as substrate.
As above-mentioned silane coupling agent, from the view point of raising such as, with the excellent effect of the cementability of substrate etc., when being used as sealing material for liquid crystal display device, suppression curable resin, to the outflow in liquid crystal, preferably uses 3-TSL 8330,3-mercaptopropyi Trimethoxy silane, 3-glycidoxypropyltrime,hoxysilane, 3-isocyanic ester propyl trimethoxy silicane etc. These silane coupling agents can be used alone, it is also possible to and with two or more.
The preferred lower limit of the content of the above-mentioned silane coupling agent in Photocurable resin composition 100 weight part of the present invention is 0.1 weight part, it is preferable that the upper limit is 20 weight parts. If the content of above-mentioned silane coupling agent is less than 0.1 weight part, then sometimes cannot give full play to the effect coordinating silane coupling agent to produce. If the content of above-mentioned silane coupling agent is greater than 20 weight parts, then sometimes cause liquid crystal pollution when the Photocurable resin composition obtained is used for sealing material for liquid crystal display device.The preferred lower limit of the content of above-mentioned silane coupling agent is 0.5 weight part, it is more preferable to the upper limit be 10 weight parts.
The Photocurable resin composition of the present invention can also contain opalizer. By containing above-mentioned opalizer, the Photocurable resin composition of the present invention can be used as shading sealing agent suitablely.
As above-mentioned opalizer, include, for example: ferric oxide, titanium are black, nigrosine, Cyanine Black, soccerballene, carbon black, resin-coated type carbon black etc. Wherein, it is preferable that titanium is black.
Above-mentioned titanium is black, compared with the average transmittance of the light for wavelength 300～800nm, near ultra-violet region, material that particularly transmissivity of the light of wavelength 370～450nm is higher. That is, above-mentioned titanium is black is the opalizer with following character: by fully covering the light of the wavelength of visible region, and gives opacifying property to the Photocurable resin composition of the present invention, on the other hand, makes the Transmission light of the wavelength near ultra-violet region. As the present invention Photocurable resin composition contained by opalizer, it is preferable to the material that insulativity is high, as the opalizer that insulativity is high, it is also preferred that titanium is black.
The optical concentration (OD value) of every 1 μm that above-mentioned titanium is black is preferably more than 3, it is more preferable to be more than 4. The opacifying property that above-mentioned titanium is black is more high more good, for the OD value that above-mentioned titanium is black, it does not have the preferred upper limit, but is generally less than 5.
For above-mentioned titanium is black, even if not surface treated titanium is black, also sufficient effect can be played, but the titanium that the titanium that surface can also be used to process through organic compositions such as coupling agents is black or the inorganic components such as oxidized silicon, titanium dioxide, acidifying germanium, aluminum oxide, zirconium white, magnesium oxide covers is black etc., and surface treated titanium is black. Wherein, from the viewpoint of further improve insulativity, it is preferable that the titanium processed through organic composition is black.
In addition, use, containing the black liquid crystal display device manufactured as sealing material for liquid crystal display device as the Photocurable resin composition of the present invention of opalizer of above-mentioned titanium, there is sufficient opacifying property, therefore, there is no spilling of light and there is high-contrast, it is possible to realize the liquid crystal display device with excellent display quality of image.
As above-mentioned titanium black among commercially available product, include, for example: 12S, 13M, 13M-C, 13R-N, 14M-C (be MitsubishiMaterials company manufacture), TilackD (red fringe chemical conversion company manufacture) etc.
The preferred lower limit of the specific surface area that above-mentioned titanium is black is 13m2/ g, it is preferable that the upper limit be 30m2/ g, it is more preferable to lower limit be 15m2/ g, it is more preferable to the upper limit be 25m2/g。
In addition, the preferred lower limit of the volume resistance that above-mentioned titanium is black is 0.5 Ω cm, it is preferable that the upper limit be 3 Ω cm, it is more preferable to lower limit be 1 Ω cm, it is more preferable to the upper limit be 2.5 Ω cm.
If below the distance between the substrate of the primary particle size liquid crystal display device etc. of above-mentioned opalizer, being not particularly limited, it is preferable that lower limit be 1nm, it is preferable that the upper limit be 5 μm. If the primary particle size of above-mentioned opalizer is lower than 1nm, then viscosity, the thixotropy of the Photocurable resin composition obtained significantly increase, and operability is deteriorated sometimes. If the primary particle size of above-mentioned opalizer is greater than 5 μm, then the coating of the Photocurable resin composition obtained is deteriorated sometimes. The preferred lower limit of the primary particle size of above-mentioned opalizer is 5nm, it is more preferable to the upper limit be 200nm, further preferred lower limit is 10nm, and the preferred upper limit is 100nm further.
The preferred lower limit of the content of the above-mentioned opalizer in Photocurable resin composition 100 weight part of the present invention is 5 weight parts, it is preferable that the upper limit is 80 weight parts. If the content of above-mentioned opalizer is less than 5 weight parts, then sometimes cannot obtain sufficient opacifying property. If the content of above-mentioned opalizer is greater than 80 weight parts, then the decrease in strength after the adaptation to substrate of the Photocurable resin composition sometimes obtained, solidification, or illustrative decline. The preferred lower limit of the content of above-mentioned opalizer is 10 weight parts, it is more preferable to the upper limit be 70 weight parts, further preferred lower limit is 30 weight parts, and the preferred upper limit is 60 weight parts further.
As the method for the Photocurable resin composition manufacturing the present invention, include, for example following method etc.: use the mixing machines such as even decollator, homogeneous mixer, universal mixer, planetary-type mixer, kneader, three-roller, by the macromolecular compound of the polymerizable monomer of curable resin, the present invention and/or the present invention and other Photoepolymerizationinitiater initiater added as required, the mixing of other additive such as sensitizing agent, silane coupling agent.
The Photocurable resin composition of the present invention is preferably used as sealing material for liquid crystal display device.
The sealing material for liquid crystal display device using the Photocurable resin composition of the present invention and make also is one of the present invention.
By coordinating electrically conductive microparticle in the sealing material for liquid crystal display device of the present invention, it is possible to manufacture upper and lower conductive material. The conductive material up and down of such sealing material for liquid crystal display device containing the present invention and electrically conductive microparticle is also one of the present invention.
As above-mentioned electrically conductive microparticle, it is possible to use Metal Ball, the particulate etc. being formed with conductive metal layer on the surface of resin particle. Wherein, from the view point of conduction can be carried out when not damaging transparency carrier etc. by the excellent resilience of resin particle connect, it is preferable that be formed with the particulate of conductive metal layer on the surface of resin particle.
The liquid crystal display device using the sealing material for liquid crystal display device of the present invention or the manufacture of conductive material up and down of the present invention is also one of the present invention.
As the method for the liquid crystal display device manufacturing the present invention, include, for example the method etc. with following operation: with, in a slice in 2 transparency carriers such as the glass substrate of the electrodes such as ito thin film or polyethylene terephthalate substrate, being made the sealing material for liquid crystal display device etc. of the present invention form the operation of rectangular seal pattern by silk screen printing, divider coating etc.; When the sealing material for liquid crystal display device etc. of the present invention does not solidify, the tiny droplets of liquid crystal is dripped and it is applied in the frame of transparency carrier on whole, immediately the operation of another substrate overlapping; With light such as the seal pattern part irradiation ultraviolet radiations of the sealing material for liquid crystal display device etc. to the present invention, thus the operation making sealing agent temporary fixing; And temporary fixing sealing agent is heated and make it the operation of main solidification.
The effect of invention
According to the present invention, it is provided that the pollution of liquid crystal is low, to highly sensitive, the polymerizable monomer that sensitization effect is also excellent of the light of long wavelength and macromolecular compound that the polymerization of this polymerizable monomer is obtained. In addition, according to the present invention, it is provided that containing this polymerizable monomer and/or the Photocurable resin composition of this macromolecular compound, the sealing material for liquid crystal display device using this Photocurable resin composition and make and the conductive material up and down using this sealing material for liquid crystal display device and manufacturing and liquid crystal display device.
Accompanying drawing explanation
Fig. 1 schematically shows to be used in each sealing material for liquid crystal display device obtained in embodiment and comparative example and with the sectional view of the liquid crystal display device made by the state without light shielding part.
Fig. 2 schematically shows to be used in each sealing material for liquid crystal display device obtained in embodiment and comparative example and the sectional view there to be the liquid crystal display device made by the state of light shielding part.
Embodiment
Hereinafter enumerate embodiment, the present invention is specifically described further, but the present invention is not limited in these embodiments.
(making of polymerizable monomer A)
By compound 16.5 weight part shown in formula (2-1) and the R shown in formula (6-1)1For compound 6.4 weight part of hydrogen, as under the existence of PS-PPH3 (BiotageJapan Inc., the basic catalyst having carried triphenylphosphine in the middle load of polystyrene (PS)) 0.7 weight part of basic catalyst, stir 48 hours limits in 110 DEG C of limits to react, thus obtain the R shown in formula (7-1)1For the compound (polymerizable monomer A) of hydrogen.
It should be noted that, the compound shown in formula (2-1) and the R shown in formula (6-1)1For the mixing ratio of compound of hydrogen is the compound shown in formula (2-1) taking molar ratio computing: the R shown in formula (6-1)1Compound=2 for hydrogen: 1.
(making of macromolecular compound A)
The polymerizable monomer A10 weight part obtained is carried out nitrogen displacement limit 70 DEG C of stirrings 7 hours below in the existence of Diisopropyl azodicarboxylate 0.5 weight part as polymerization starter, reacts simultaneously, thus obtain macromolecular compound A. The number-average molecular weight of the macromolecular compound A obtained is 14200 (polymerization degree 50).
(making of polymerizable monomer B)
By compound 16.5 weight part shown in formula (2-2) and the R shown in formula (6-1)1For compound 5.5 weight part of hydrogen, as under the existence of PS-PPH3 (BiotageJapan Inc., the basic catalyst having carried triphenylphosphine in the middle load of polystyrene (PS)) 0.7 weight part of basic catalyst, stir limit reaction in 48 hours in 110 DEG C of limits, thus obtain the R shown in formula (7-2)1For the compound (polymerizable monomer B) of hydrogen.
It should be noted that, the compound shown in formula (2-2) and the R shown in formula (6-1)1For the mixing ratio of compound of hydrogen is the compound shown in formula (2-2) taking molar ratio computing: the R shown in formula (6-1)1Compound=85.3 for hydrogen: 42.9.
(making of macromolecular compound B)
The polymerizable monomer B10 weight part obtained is carried out nitrogen displacement limit 70 DEG C of stirrings 7 hours below in the existence of Diisopropyl azodicarboxylate 0.5 weight part as polymerization starter, reacts simultaneously, thus obtain macromolecular compound B. The number-average molecular weight of the macromolecular compound B obtained is 12900 (polymerization degree 40).
(making of polymerizable monomer C)
By compound 16.5 weight part shown in formula (2-3) and the R shown in formula (6-1)1For compound 4.1 weight part of hydrogen, as under the existence of PS-PPH3 (BiotageJapan Inc., the basic catalyst having carried triphenylphosphine in the middle load of polystyrene (PS)) 0.7 weight part of basic catalyst, stir 48 hours limits in 110 DEG C of limits to react, thus obtain the R shown in formula (7-3)1For the compound (polymerizable monomer C) of hydrogen.
It should be noted that, the compound shown in formula (2-3) and the R shown in formula (6-1)1For the mixing ratio of compound of hydrogen is the compound shown in formula (2-3) taking molar ratio computing: the R shown in formula (6-1)1Compound=63.2 for hydrogen: 32.0.
(making of macromolecular compound C)
The polymerizable monomer C10 weight part obtained is carried out nitrogen displacement limit 70 DEG C of stirrings 7 hours below in the existence of Diisopropyl azodicarboxylate 0.5 weight part as polymerization starter, reacts simultaneously, thus obtain macromolecular compound C. The number-average molecular weight of the macromolecular compound C obtained is 10200 (polymerization degree 26).
(making of polymerizable monomer D)
By compound 16.5 weight part shown in formula (2-1) and all R shown in formula (6-2)2For compound 11.8 weight part of methoxyl group, as under the existence of PS-PPH3 (BiotageJapan Inc., the basic catalyst having carried triphenylphosphine in the middle load of polystyrene (PS)) 0.7 weight part of basic catalyst, stir 48 hours limits in 110 DEG C of limits to react, thus obtain the compound shown in formula (7-4) (polymerizable monomer D).
It should be noted that, the compound shown in formula (2-1) and all R shown in formula (6-2)2For the mixing ratio of compound of methoxyl group is the compound shown in formula (2-1) taking molar ratio computing: all R shown in formula (6-2)2Compound=2 for methoxyl group: 1.
(making of macromolecular compound D)
The polymerizable monomer D10 weight part obtained is carried out nitrogen displacement limit 70 DEG C of stirrings 7 hours below in the existence of Diisopropyl azodicarboxylate 0.5 weight part as polymerization starter, reacts simultaneously, thus obtain macromolecular compound D. The number-average molecular weight of the macromolecular compound D obtained is 8900 (polymerization degree 22).
(making of polymerizable monomer E)
By compound 16.5 weight part shown in formula (5-1) and the R shown in formula (6-1)1React for compound 3.7 weight part of hydrogen stirs 48 hours limits in 110 DEG C of limits under as the existence of PS-PPH3 (BiotageJapan Inc., in the polystyrene (PS) load carried the basic catalyst of triphenylphosphine) 0.7 weight part of basic catalyst, thus obtain the R shown in formula (8-1)1For the compound (polymerizable monomer E) of hydrogen.
It should be noted that, the compound shown in formula (5-1) and the R shown in formula (6-1)1For the mixing ratio of compound of hydrogen is the compound shown in formula (5-1) taking molar ratio computing: the R shown in formula (6-1)1Compound=57.63 for hydrogen: 28.9.
(making of macromolecular compound E)
The polymerizable monomer E10 weight part obtained at ethanol 20.0g, water 0.5g and as the existence of 6N-hydrochloric acid 0.6 weight part of acid catalyst, is carried out nitrogen circulation limit below and stirs 4 hours at 70 DEG C, reacts simultaneously, thus obtain macromolecular compound E. The number-average molecular weight of the macromolecular compound E obtained is 15200 (polymerization degree 37).
(making of polymerizable monomer F)
By compound 16.5 weight part shown in formula (5-2) and the R shown in formula (6-1)1For compound 4.7 weight part of hydrogen, as under the existence of PS-PPH3 (BiotageJapan Inc., the basic catalyst having carried triphenylphosphine in the middle load of polystyrene (PS)) 0.7 weight part of basic catalyst, stir 48 hours limits in 110 DEG C of limits to react, thus obtain the R shown in formula (8-2)1For the compound (polymerizable monomer F) of hydrogen.
It should be noted that, the compound shown in formula (5-2) and the R shown in formula (6-1)1For the mixing ratio of compound of hydrogen is the compound shown in formula (5-2) taking molar ratio computing: the R shown in formula (6-1)1Compound=72.3 for hydrogen: 36.7.
(making of macromolecular compound F)
The polymerizable monomer F10 weight part obtained at ethanol 20.0g, water 0.5g and as the existence of 6N-hydrochloric acid 0.6 weight part of acid catalyst, is carried out nitrogen circulation limit below and stirs 4 hours at 70 DEG C, reacts simultaneously, thus obtain macromolecular compound F.The number-average molecular weight of the macromolecular compound F obtained is 16500 (polymerization degree 46).
(making of polymerizable monomer G)
By compound 16.5 weight part shown in formula (5-1) and all R shown in formula (6-2)2For compound 6.8 weight part of methoxyl group stirs 48 hours limits in 110 DEG C of limits react at PS-PPH3 (BiotageJapan Inc., the basic catalyst having carried triphenylphosphine in the middle load of polystyrene (PS)) 0.7 weight part as basic catalyst, thus obtain the compound shown in formula (8-3) (polymerizable monomer G).
It should be noted that, the compound shown in formula (5-1) and all R shown in formula (6-2)2For the mixing ratio of compound of methoxyl group is the compound shown in formula (5-1) taking molar ratio computing: all R shown in formula (6-2)2Compound=57.6 for methoxyl group: 28.8.
(making of macromolecular compound G)
The polymerizable monomer G10 weight part obtained at ethanol 20.0g, water 0.5g and as the existence of 6N-hydrochloric acid 0.6 weight part of acid catalyst, is carried out nitrogen circulation limit below and stirs 4 hours in 70 DEG C, reacts simultaneously, thus obtain macromolecular compound G. The number-average molecular weight of the macromolecular compound G obtained is 7600 (polymerization degree 15).
(embodiment 1～17, comparative example 1)
According to proportioning described in table 1,2, it may also be useful to planetary stirring machine (Thinky Inc., " あ わ と りTaro ") after each material mixing, three-roller will be used further to mix, thus prepare each sealing material for liquid crystal display device of embodiment 1～17, comparative example 1.
<evaluation>
Following evaluation is carried out for each sealing material for liquid crystal display device obtained in embodiment and comparative example. Show the result in table 1,2.
(light solidified)
On the glass substrate taking the gap after glass adhering substrate as the mode of about 5 μm is coated in embodiment and comparative example each sealing material for liquid crystal display device obtained, the glass substrate of overlapping identical size on the substrate, then, it may also be useful to metal halide light irradiation 100mW/cm2Ultraviolet (wavelength 365nm) 10 seconds. Use infrared spectroscopy device (BIORAD Inc., " FTS3000 "), measure the variable quantity of the peak being derived from (methyl) acryl before and after illumination is penetrated, thus carry out the evaluation of light solidified. The situation of peak minimizing more than 93% that will be derived from (methyl) acryl after illumination is penetrated is as " ◎ "; the peak being derived from (methyl) acryl after illumination is penetrated is reduced more than 85% and be less than 93% situation as "○"; the peak being derived from (methyl) acryl after illumination is penetrated is reduced more than 75% and be less than 85% situation as " △ "; the situation that the minimizing being derived from the peak of (methyl) acryl after illumination is penetrated is less than 75% is as "×", thus have rated light solidified.
(liquid crystal pollution)
Each sealing material for liquid crystal display device 100 weight part obtained in embodiment and comparative example disperses spacer particulate (ponding chemical industry Inc., " MicropearlSI-H050 ") 1 weight part and makes sealing material for liquid crystal display device, to make the live width of sealing agent utilize divider to be coated with as the mode of 1mm in a slice in 2 substrates with the alignment films after grinding and transparency electrode.
Then the tiny droplets of liquid crystal (Chisso Inc., " JC-5004LA ") is dripped the sealing agent being applied to the substrate with transparency electrode frame on whole, fit immediately another colour filtering chip basic board with transparency electrode, it may also be useful to sealing agent part is irradiated 100mW/cm by metal halide lamp2Ultraviolet (wavelength 365nm) 30 seconds and make it solidification, further with 120 DEG C heat 1 hour and obtain liquid crystal display device.
Make the following two kinds liquid crystal display device: the liquid crystal display device (without light shielding part) using the divider control application place of sealing agent and sealing agent is arrived by illumination completely; And the liquid crystal display device (having light shielding part) being coated with sealing agent and obtain in the way of the 50% of live width with the black matrix" of colour filtering chip basic board overlap joint. Fig. 1 schematically shows to be used in each sealing material for liquid crystal display device obtained in embodiment and comparative example and with the sectional view of the liquid crystal display device made by the state without light shielding part, and Fig. 2 schematically shows to be used in each sealing material for liquid crystal display device obtained in embodiment and comparative example and the sectional view there to be the liquid crystal display device made by the state of light shielding part. As shown in Figure 1, sealing agent 1 is the state that sealing agent 1 is arrived by illumination completely without the liquid crystal display device of light shielding part, on the other hand, the liquid crystal display device that sealing agent 1 has light shielding part as shown in Figure 2, the sealing agent 1 of the part contacted with liquid crystal 3 covered by black matrix" 2 and completely according to less than light.
The liquid crystal display device obtained is carried out the test run(s) of 100 hours, then by visually the liquid crystal aligning disorder near the sealing agent after reaching the state applying 1000 hours voltage at 80 DEG C having been confirmed.
Orientation disorder is judged by the irregular colour in display portion, degree according to irregular colour, the average evaluation not having irregular colour completely is " ◎ ", is "○" by the average evaluation slightly having irregular colour, is " △ " by average evaluation few for irregular colour, is "×" by average evaluation quite a lot of for irregular colour, thus have rated liquid crystal pollution.
It should be noted that, be evaluated as " ◎ ", the liquid crystal display device of "○" be practical on completely no problem grade.
[table 1]
[table 2]
Utilizability in industry
According to the present invention, it is provided that the pollution of liquid crystal is low, to highly sensitive, the polymerizable monomer that sensitization effect is also excellent of the light of long wavelength and macromolecular compound that the polymerization of this polymerizable monomer is obtained. In addition, according to the present invention, it is provided that Photocurable resin composition, the sealing material for liquid crystal display device using this Photocurable resin composition and make containing this polymerizable monomer and/or this macromolecular compound and use the conductive material up and down manufactured by this sealing material for liquid crystal display device and liquid crystal display device.
Nomenclature
1, sealing agent
2, black matrix"
3, liquid crystal
Claims (11)
1. a polymerizable monomer, it is characterized in that, make dialkyl amino yl benzoic acid based compound or have can with the thioxanthone derivates of the functional group of epoxy reaction and have unsaturated double-bond epoxy compounds or have alkoxysilyl epoxy compounds reaction obtain.
2. polymerizable monomer as claimed in claim 1, it is characterized in that, dialkyl amino yl benzoic acid based compound is the compound shown in the compound shown in following formula (2-1), formula (2-2) or the compound shown in formula (2-3)
3. polymerizable monomer as claimed in claim 1, it is characterised in that, thioxanthone derivates is the compound shown in following formula (5-1) or formula (5-2),
4. polymerizable monomer as described in claim 1,2 or 3, it is characterised in that, epoxy compounds is the compound shown in following formula (6-1) or formula (6-2),
In formula (6-1), R1Represent hydrogen or methyl, in formula (6-2), R2Represent carbon number be 1～10 alkyl or carbon number be the alkoxyl group of 1～10, each R2Can be the same or different, at least 1 R2Be carbon number it is the alkoxyl group of 1～10.
5. a macromolecular compound, it is characterised in that, the polymerizable monomer polymerization described in claim 1,2,3 or 4 is obtained.
6. macromolecular compound as claimed in claim 5, it is characterised in that, the polymerization degree is more than 3.
7. a Photocurable resin composition, it is characterised in that, containing curable resin, also containing the polymerizable monomer described in claim 1,2,3 or 4 and/or the macromolecular compound described in claim 5 or 6.
8. Photocurable resin composition as claimed in claim 7, it is characterised in that, containing opalizer.
9. a sealing material for liquid crystal display device, it is characterised in that, use the Photocurable resin composition described in claim 7 or 8 to make.
10. about one kind conductive material, it is characterised in that, containing sealing material for liquid crystal display device according to claim 9 and electrically conductive microparticle.
11. 1 kinds of liquid crystal display device, it is characterised in that, use the sealing material for liquid crystal display device described in claim 9 or upper and lower conductive material according to claim 10 to manufacture.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2013252325 | 2013-12-05 | ||
| JP2013-252325 | 2013-12-05 | ||
| PCT/JP2014/081737 WO2015083663A1 (en) | 2013-12-05 | 2014-12-01 | Polymerizable monomer, polymer compound, photocurable resin composition, sealing element for liquid crystal display element, vertical conduction material, and liquid crystal display element |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105683225A true CN105683225A (en) | 2016-06-15 |
| CN105683225B CN105683225B (en) | 2019-09-03 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201480058891.4A Active CN105683225B (en) | 2013-12-05 | 2014-12-01 | Sealing material for liquid crystal display device, upper and lower conductive material and liquid crystal display element |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP6434901B2 (en) |
| KR (1) | KR102256146B1 (en) |
| CN (1) | CN105683225B (en) |
| TW (1) | TWI641582B (en) |
| WO (1) | WO2015083663A1 (en) |
Cited By (5)
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| CN109564371A (en) * | 2016-12-16 | 2019-04-02 | 积水化学工业株式会社 | Polymerizable compound, sealing material for liquid crystal display device, upper and lower conductive material and liquid crystal display element |
| CN110168442A (en) * | 2017-07-14 | 2019-08-23 | 积水化学工业株式会社 | Sealing material for liquid crystal display device, upper and lower conductive material and liquid crystal display element |
| CN114805296A (en) * | 2022-05-10 | 2022-07-29 | 艾坚蒙(安庆)科技发展有限公司 | Thioxanthone derivative, preparation method and application thereof |
| CN115322328A (en) * | 2022-08-19 | 2022-11-11 | 武汉长盈鑫科技有限公司 | Preparation method of low-energy fast-curing epoxy modified polyurethane acrylate |
| CN115996959A (en) * | 2020-09-30 | 2023-04-21 | 积水化学工业株式会社 | Thioxanthone compound, photopolymerization initiator, curable resin composition, composition for display element, sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6097454B1 (en) * | 2015-09-02 | 2017-03-15 | 積水化学工業株式会社 | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element |
| KR20210082126A (en) * | 2018-10-26 | 2021-07-02 | 세키스이가가쿠 고교가부시키가이샤 | Sealing agent for liquid crystal display elements, vertical conduction material, and liquid crystal display element |
| EP4310105A1 (en) * | 2022-07-20 | 2024-01-24 | Arkema France | Acrylic copolymers imparting low yellowing after photocuring |
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Also Published As
| Publication number | Publication date |
|---|---|
| TWI641582B (en) | 2018-11-21 |
| TW201538461A (en) | 2015-10-16 |
| KR102256146B1 (en) | 2021-05-25 |
| CN105683225B (en) | 2019-09-03 |
| JP6434901B2 (en) | 2018-12-05 |
| WO2015083663A1 (en) | 2015-06-11 |
| JPWO2015083663A1 (en) | 2017-03-16 |
| KR20160094929A (en) | 2016-08-10 |
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