CN105339839A - Liquid-crystal-display-element sealant, vertical conductive material, and liquid-crystal display element - Google Patents
Liquid-crystal-display-element sealant, vertical conductive material, and liquid-crystal display element Download PDFInfo
- Publication number
- CN105339839A CN105339839A CN201480035646.1A CN201480035646A CN105339839A CN 105339839 A CN105339839 A CN 105339839A CN 201480035646 A CN201480035646 A CN 201480035646A CN 105339839 A CN105339839 A CN 105339839A
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- China
- Prior art keywords
- liquid crystal
- crystal display
- methyl
- display device
- sealing material
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- 239000004020 conductor Substances 0.000 title claims abstract description 12
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims abstract description 14
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- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims abstract description 8
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims abstract description 8
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- VIYUEVOEZUVFSN-UHFFFAOYSA-N CC(CC1=C(C=CC(=C1C(=O)OC)C(=O)O)CCOC(=O)C=C)O Chemical compound CC(CC1=C(C=CC(=C1C(=O)OC)C(=O)O)CCOC(=O)C=C)O VIYUEVOEZUVFSN-UHFFFAOYSA-N 0.000 description 1
- CYYLGOYEORUYJD-UHFFFAOYSA-N CN(C)C=1C(=C(C(=O)Cl)C=CC1)Cl Chemical class CN(C)C=1C(=C(C(=O)Cl)C=CC1)Cl CYYLGOYEORUYJD-UHFFFAOYSA-N 0.000 description 1
- 244000205754 Colocasia esculenta Species 0.000 description 1
- 235000006481 Colocasia esculenta Nutrition 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- IIGAAOXXRKTFAM-UHFFFAOYSA-N N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C Chemical compound N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C IIGAAOXXRKTFAM-UHFFFAOYSA-N 0.000 description 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 1
- MBOZGLMBKQFIBB-UHFFFAOYSA-N N=C=O.OP(O)(=S)OC1=CC=CC=C1 Chemical compound N=C=O.OP(O)(=S)OC1=CC=CC=C1 MBOZGLMBKQFIBB-UHFFFAOYSA-N 0.000 description 1
- QSBINWBNXWAVAK-PSXMRANNSA-N PE-NMe(16:0/16:0) Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCNC)OC(=O)CCCCCCCCCCCCCCC QSBINWBNXWAVAK-PSXMRANNSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-ISLYRVAYSA-N V-65 Substances CC(C)CC(C)(C#N)\N=N\C(C)(C#N)CC(C)C WYGWHHGCAGTUCH-ISLYRVAYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 150000007973 cyanuric acids Chemical class 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- ZWLIYXJBOIDXLL-UHFFFAOYSA-N decanedihydrazide Chemical compound NNC(=O)CCCCCCCCC(=O)NN ZWLIYXJBOIDXLL-UHFFFAOYSA-N 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 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
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000013007 heat curing 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
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 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
- 229920001427 mPEG Polymers 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 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
- 125000005641 methacryl group Chemical group 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
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-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
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000728 polyester Polymers 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
- 230000005855 radiation Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 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
- 229910021647 smectite Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000001384 succinic acid Substances 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
- 238000012719 thermal polymerization Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical compound [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/378—Thiols containing heterocyclic rings
-
- 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
-
- 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
-
- 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
- G02F2202/00—Materials and properties
- G02F2202/28—Adhesive materials or arrangements
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nonlinear Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Mathematical Physics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Sealing Material Composition (AREA)
- Liquid Crystal (AREA)
- Polymerization Catalysts (AREA)
- Conductive Materials (AREA)
- Polymerisation Methods In General (AREA)
Abstract
One purpose of this invention is to provide a liquid-crystal-display-element sealant that exhibits excellent photocrosslinking performance and can reduce liquid-crystal contamination. Another purpose of this invention is to provide a vertical conductive material and a liquid-crystal display element using the aforementioned liquid-crystal-display-element sealant. This invention is a liquid-crystal-display-element sealant containing a thioxanthone-based polymerization initiator and an amine-based sensitizer that can be represented by formula (1). In formula (1), z represents an integer greater than or equal to 1; and P represents (poly)ethylene glycol, (poly)propylene glycol, (poly)butylene glycol, glycerin, trimethylolpropane, ditrimethylolpropane, pentaerythritol, dipentaerythritol, or a caprolactone polyol residue.
Description
Technical field
The present invention relates to a kind of photo-curable excellent and the sealing material for liquid crystal display device of liquid crystal pollution can be suppressed.In addition, the present invention relates to and a kind ofly use this sealing material for liquid crystal display device and the conductive material up and down made and liquid crystal display cells.
Background technology
In recent years, as the manufacture method of the liquid crystal display cells such as liquid crystal display, from shortening pitch time, using the viewpoint such as optimization of amount of liquid crystal to consider, use the photo-thermal that to employ disclosed in patent documentation 1, patent documentation 2 containing curable resin, Photoepolymerizationinitiater initiater and thermal curing agents and with the sealant of curing type, the liquid crystal drop under type that is called as technique of dripping.
Dripping in technique, first, 2 a slices with the substrate of electrode are forming rectangular seal pattern by divider.Then, drip in the sealing frame of substrate under the state that sealant is uncured by the tiny droplets of liquid crystal, another plate base overlapping, carries out temporary fixing to light such as sealing irradiation ultraviolet radiations under vacuo.Thereafter, implement heating and carry out main solidification, making liquid crystal display cells.At present, this technique of dripping has become the main flow of the manufacture method of liquid crystal display cells.
In addition, in the various modern times popularized with the mobile device of liquid crystal panel such as portable phone, portable game, the small-sized of equipment turns to the problem wishing most to realize.As the method for the miniaturization of equipment, the narrow frame of liquid crystal display part can be enumerated, such as, the position of sealing is configured at (hereinafter also referred to as narrow frame design) under black matrix".
But, in narrow frame design, sealant is configured at immediately below black matrix", if therefore implement to drip technique, the then light crested of the irradiation when making sealant carry out photocuring, and there is light and be difficult to arrive the inside of sealant, solidification becomes insufficient problem.If the solidification of sealant becomes insufficient like this, then there is the problem easily producing liquid crystal pollution in uncured sealant composition stripping to liquid crystal.
In patent documentation 3, disclose and highly sensitive Photoepolymerizationinitiater initiater is engaged in sealant.But, if only coordinate highly sensitive Photoepolymerizationinitiater initiater, then cannot make sealant photocuring fully.In addition, in patent documentation 4, disclose and highly sensitive Photoepolymerizationinitiater initiater and sensitizer are combined and be engaged in sealant.But, owing to using sensitizer, therefore there is the problem easily producing liquid crystal pollution.
Prior art document
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
Invent problem to be solved
The object of the invention is to, provide a kind of photo-curable excellent and the sealing material for liquid crystal display device of liquid crystal pollution can be suppressed.In addition, the object of the invention is to, provide a kind of and use this sealing material for liquid crystal display device and the conductive material up and down made and liquid crystal display cells.
For the method for dealing with problems
The present invention is the sealing material for liquid crystal display device containing the amine system sensitizer represented by curable resin, thioxanthones system polymerization initiator and following formula (1).
[changing 1]
In formula (1), z represents the integer of more than 1, and P is the residue of (gathering) ethylene glycol, (gathering) propylene glycol, (gathering) butylene glycol, glycerine, trimethylolpropane, two (trihydroxy methyl) propane, pentaerythrite, dipentaerythritol or caprolactone polyol.
Below explain the present invention.
The discoveries such as the present inventor, surprisingly, the contaminative of compound to liquid crystal with specific structure is lower, and sensibilization is excellent.Therefore, the discoveries such as the present inventor: by coordinating this compound as sensitizer, can obtain photo-curable excellence and can suppress the sealing material for liquid crystal display device of liquid crystal pollution, thus completing the present invention.
Sealing material for liquid crystal display device of the present invention contains the amine system sensitizer represented by above-mentioned formula (1).By the amine system sensitizer represented by above-mentioned formula (1) and thioxanthones system polymerization initiator being contained in combination, thus it is excellent and can suppress the sealant of liquid crystal pollution to make sealing material for liquid crystal display device of the present invention become high sensitivity and photo-curable.
In above-mentioned formula (1), z represents the integer of more than 1, and preferred lower limit is 2, and the preferred upper limit is 6.If above-mentioned z is less than 2, then sometimes cause liquid crystal pollution.If above-mentioned z is more than 6, then viscosity uprises, and process sometimes becomes difficulty.
In above-mentioned formula (1), P is the residue of (gathering) ethylene glycol, (gathering) propylene glycol, (gathering) butylene glycol, glycerine, trimethylolpropane, two (trihydroxy methyl) propane, pentaerythrite, dipentaerythritol or caprolactone polyol.
The preferred lower limit of the molecular weight of the P in above-mentioned formula (1) is 100, and the preferred upper limit is 2000.If the molecular weight of P is less than 100, then sometimes cause liquid crystal pollution.If the molecular weight of P is more than 2000, then viscosity becomes too high, and process sometimes becomes difficulty.
About the amine system sensitizer represented by above-mentioned formula (1), the z be preferably in formula (1) is 2 and P is the residue of polyglycol.
As the method for the amine system sensitizer manufactured represented by above-mentioned formula (1), specifically, include, for example the method etc. that 4 (dimethylamino) chlorobenzoyl chlorides and polyethylene oxide are reacted.
The preferred lower limit of the content of the amine system sensitizer represented by above-mentioned formula (1) in sealing material for liquid crystal display device 100 weight portion of the present invention is 0.1 weight portion, and preferred upper limit is 10 weight portions.If the content of the amine system sensitizer represented by above-mentioned formula (1) is less than 0.1 weight portion, then obtained sealing material for liquid crystal display device becomes the sealant of photo-curable difference, sometimes produces liquid crystal pollution.If the content of the amine system sensitizer represented by above-mentioned formula (1) is more than 10 weight portions, then sometimes produce because of the liquid crystal pollution caused by the amine system sensitizer represented by above-mentioned formula (1).More preferably the lower limit of the content of the amine system sensitizer represented by above-mentioned formula (1) is 0.3 weight portion, and more preferably the upper limit is 7 weight portions.
Sealing material for liquid crystal display device of the present invention contains thioxanthones system polymerization initiator.
As above-mentioned thioxanthones system polymerization initiator, include, for example: the compound represented by following formula (2), 2,4-diethyl thioxanthones, ITX, ITX, CTX, the chloro-4-propoxythioxanthone of 1-etc.Wherein, the sealant of curability excellence is become from the viewpoint of obtained sealing material for liquid crystal display device, be preferably the compound (hereinafter also referred to as " the thioxanthones system polymerization initiator represented by formula (2) ") represented by following formula (2).
[changing 2]
In formula (2), n is 1 ~ 6, R
3for hydrogen atom, methyl or ethyl, when n is greater than 1, R
3represented group or atom can be the same or different; A expression-O-,-[O (CHR
2cHR
1)
a]
y-,-[O (CH
2)
bcO]
y-or ,-[O (CH
2)
bcO]
(y-1)-[O (CHR
2cHR
1)
a]-group, R
1and R
2in one represent hydrogen atom, another one represents hydrogen atom, methyl or ethyl, a is 1 ~ 2, b is 4 ~ 5, Q is the residue of (gathering) ethylene glycol, (gathering) propylene glycol, (gathering) butylene glycol, glycerine, trimethylolpropane, two (trihydroxy methyl) propane, pentaerythrite, dipentaerythritol or caprolactone polyol, free hydroxyl group in Q can be esterified, x is the number being greater than 1 and being no more than the hydroxyl value of Q, when x is greater than 1 and is no more than 2, y is 1 ~ 10, when x is more than 2, y is 3 ~ 10.
In above-mentioned formula (2), x is the number being greater than 1 and being no more than the hydroxyl value of Q, and preferred lower limit is 2, and the preferred upper limit is 6.If above-mentioned x is less than 2, then sometimes cause liquid crystal pollution.If above-mentioned x is more than 6, then viscosity uprises, and operation sometimes becomes difficulty.
Thioxanthones system polymerization initiator represented by above-mentioned formula (2) is preferably: the n in above-mentioned formula (2) is 1, R
3for hydrogen atom, A is the group of formula-O-.
Q in above-mentioned formula (2) is preferably the residue of polytetramethylene glycol.
In addition, in the esterified situation of the free hydroxyl group in Q, the thioxanthones system polymerization initiator represented by above-mentioned formula (2) is preferably low-grade fatty acid ester.
In above-mentioned formula (2), the preferred lower limit of the molecular weight of A-Q is 100, and preferred upper limit is 2000.If the molecular weight of A-Q is less than 100, then sometimes cause liquid crystal pollution.If the molecular weight of A-Q is more than 2000, then viscosity becomes too high, and process sometimes becomes difficulty.
As the method for the thioxanthones system polymerization initiator manufactured represented by above-mentioned formula (2), specifically, include, for example the method etc. that send as an envoy to carboxymethoxythioxanthone and polyglycol react.
The preferred lower limit of the content of the above-mentioned thioxanthones system polymerization initiator in sealing material for liquid crystal display device 100 weight portion of the present invention is 0.1 weight portion, and preferred upper limit is 10 weight portions.If the content of above-mentioned thioxanthones system polymerization initiator is less than 0.1 weight portion, then the photopolymerization of sometimes obtained sealing material for liquid crystal display device is not carried out fully.If the content of above-mentioned thioxanthones system polymerization initiator is more than 10 weight portions, then unreacted thioxanthones system polymerization initiator remains in a large number, and sometimes obtained sealing material for liquid crystal display device becomes the sealant of weatherability or storage stability difference or produces liquid crystal pollution.More preferably the lower limit of the content of above-mentioned thioxanthones system polymerization initiator is 0.3 weight portion, and more preferably the upper limit is 7 weight portions.
Proportional about containing of the amine system sensitizer represented by above-mentioned thioxanthones system polymerization initiator and above-mentioned formula (1), with mass ratio range, be preferably thioxanthones system polymerization initiator: amine system sensitizer=1 represented by formula (1): 0.05 ~ 1: 5.Amine system sensitizer represented by above-mentioned thioxanthones system polymerization initiator and above-mentioned formula (1) containing proportional within the scope of this, therefore sealing material for liquid crystal display device of the present invention becomes the effect that suppresses liquid crystal pollution and the excellent especially sealant of photo-curable.Above-mentioned thioxanthones system polymerization initiator and the amine system sensitizer represented by above-mentioned formula (1) be more preferably thioxanthones system polymerization initiator containing proportional: amine system sensitizer=1 represented by formula (1): 0.1 ~ 1: 2.
Sealing material for liquid crystal display device of the present invention contains curable resin.
Above-mentioned curable resin is preferably containing (methyl) acrylic resin.
As above-mentioned (methyl) acrylic resin, include, for example: reacted by compound and (methyl) acrylic acid making to have hydroxyl and the ester compounds obtained, epoxy (methyl) acrylate obtained by making (methyl) acrylic acid and epoxy compound react, to be reacted by (methyl) acrylic acid derivative and isocyanate compound making to have hydroxyl and carbamate (methyl) acrylate etc. that obtains.Wherein, epoxy (methyl) acrylate is preferably.It should be noted that; in this manual; above-mentioned " (methyl) acrylic acid " refers to acrylic or methacrylic acid; above-mentioned " (methyl) acrylic resin " refers to the resin with acryloyl group or methacryl (following, to be also called in the lump " (methyl) acryloyl group ").In addition, above-mentioned " (methyl) acrylate " refers to acrylate or methacrylate.In addition, above-mentioned " epoxy (methyl) acrylate " represents and the whole epoxy radicals in epoxy resin and (methyl) acrylic acid is reacted and the compound that obtains.
As the compound of the simple function in above-mentioned ester compounds, include, for example: (methyl) acrylic acid 2-hydroxyl ethyl ester, (methyl) acrylic acid 2-hydroxypropyl acrylate, (methyl) acrylic acid 4-hydroxy butyl ester, (methyl) acrylic acid 2-hydroxy butyl ester, (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) acrylic acid 2-methoxy acrylate, methoxyl ethylene glycol (methyl) acrylate, (methyl) acrylic acid 2-ethoxy ethyl ester, (methyl) acrylic acid tetrahydro furfuryl ester, (methyl) benzyl acrylate, ethyl carbitol (methyl) acrylate, (methyl) acrylate, phenoxy group diethylene glycol (methyl) acrylate, phenoxy group polyglycol (methyl) acrylate, methoxy poly (ethylene glycol) (methyl) acrylate, (methyl) acrylic acid 2,2,2-trifluoro ethyl ester, (methyl) acrylic acid 2,2,3,3-tetrafluoro propyl ester, (methyl) acrylic acid 1H, 1H, 5H-octafluoro pentyl ester, acid imide (methyl) acrylate, (methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) n-butyl acrylate, (methyl) propyl acrylate, (methyl) 2-EHA, (methyl) n-octyl, (methyl) acrylic acid ester in the different ninth of the ten Heavenly Stems, the different myristin of (methyl) acrylic acid, (methyl) acrylic acid 2-butoxyethyl, (methyl) acrylic acid 2-phenoxy ethyl, (methyl) acrylic acid dicyclopentenyloxyethyl methacrylate, (methyl) isodecyl acrylate, diethylamino ethyl (methyl) acrylate, (methyl) acrylate, succinic acid 2-(methyl) acryloyloxyethyl ester, hexahydrophthalic acid 2-(methyl) acryloyloxyethyl ester, 2-(methyl) acryloyl-oxyethyl-2-hydroxypropylphthalate, (methyl) glycidyl acrylate, 2-(methyl) acryloyl-oxyethyl phosphate etc.
In addition, as the compound of two senses in above-mentioned ester compounds, include, for example: BDO two (methyl) acrylate, 1,3-BDO two (methyl) acrylate, 1,6-hexanediol two (methyl) acrylate, 1,9-nonanediol two (methyl) acrylate, 1,10-decanediol two (methyl) acrylate, 2-normal-butyl-2-ethyl-1,3-PD 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, TEG two (methyl) acrylate, polyglycol two (methyl) acrylate, epoxypropane addition bisphenol-A two (methyl) acrylate, ethyleneoxide addition bisphenol-A two (methyl) acrylate, ethyleneoxide addition Bisphenol F two (methyl) acrylate, dihydroxymethyl dicyclopentadienyl two (methyl) acrylate, 1,3-BDO two (methyl) acrylate, neopentyl glycol two (methyl) acrylate, ethylene-oxide-modified isocyanuric acid two (methyl) acrylate, 2-hydroxyl-3-(methyl) acryloxypropyl (methyl) acrylate, carbonate diol two (methyl) acrylate, PTMEG two (methyl) acrylate, polyester-diol two (methyl) acrylate, polycaprolactone glycol two (methyl) acrylate, polybutadiene diol two (methyl) acrylate etc.
In addition, as the compound more than trifunctional in above-mentioned ester compounds, include, for example: pentaerythrite three (methyl) acrylate, trimethylolpropane tris (methyl) acrylate, epoxypropane 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, double trimethylolpropane four (methyl) acrylate, pentaerythrite four (methyl) acrylate, glycerine three (methyl) acrylate, epoxypropane addition glycerine three (methyl) acrylate, three (methyl) acryloyl-oxyethyl phosphate etc.
As above-mentioned epoxy (methyl) acrylate, include, for example out epoxy (methyl) acrylate etc. obtained by making epoxy resin and (methyl) acrylic acid carry out reacting under the existence of base catalyst according to well-established law.
As the epoxy resin of the raw material become for the synthesis of above-mentioned epoxy (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, epoxypropane addition bisphenol A type epoxy resin, resorcinol type epoxy resin, biphenyl type epoxy resin, thioether-type epoxy resin, diphenyl ether type epoxy, dicyclopentadiene-type epoxy resin, naphthalene type epoxy resin, phenol novolak type epoxy resin, o-cresol phenolic epoxy varnish, dicyclopentadiene novolac 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 in above-mentioned bisphenol A type epoxy resin, include, for example: jER828EL, jER1004 (being Mitsubishi Chemical Ind to manufacture), Epiclon850CRP (manufacture of DIC company) etc.
As the commercially available product in above-mentioned bisphenol f type epoxy resin, include, for example jER806, jER4004 (being Mitsubishi Chemical Ind to manufacture) etc.
As the commercially available product in above-mentioned bisphenol-s epoxy resin, include, for example EpiclonEXA1514 (manufacture of DIC company) etc.
As above-mentioned 2, the commercially available product in 2 '-diallyl bisphenol type epoxy resin, include, for example RE-810NM (Japanese chemical drug Inc. makes) etc.
As the commercially available product in above-mentioned A Hydrogenated Bisphenol A type epoxy resin, include, for example EpiclonEXA7015 (manufacture of DIC company) etc.
As the commercially available product in above-mentioned epoxypropane addition bisphenol A type epoxy resin, include, for example: EP-4000S (manufacture of ADEKA company) etc.
As the commercially available product in above-mentioned resorcinol type epoxy resin, include, for example EX-201 (manufacture of Nagasechemtex company) etc.
As the commercially available product in above-mentioned biphenyl type epoxy resin, include, for example jERYX-4000H (Mitsubishi Chemical Ind's manufacture) etc.
As the commercially available product in above-mentioned thioether-type epoxy resin, include, for example YSLV-50TE (Nippon Steel lives aurification company and manufactures) etc.
As the commercially available product in above-mentioned diphenyl ether type epoxy, include, for example YSLV-80DE (Nippon Steel lives aurification company and manufactures) etc.
As the commercially available product in above-mentioned dicyclopentadiene-type epoxy resin, include, for example EP-4088S (manufacture of ADEKA company) etc.
As the commercially available product in above-mentioned naphthalene type epoxy resin, include, for example EpiclonHP4032, EpiclonEXA-4700 (being DIC company to manufacture) etc.
As the commercially available product in above-mentioned phenol novolak type epoxy resin, include, for example EpiclonN-770 (manufacture of DIC company) etc.
As the commercially available product in above-mentioned o-cresol phenolic epoxy varnish, include, for example EpiclonN-670-EXP-S (manufacture of DIC company) etc.
As the commercially available product in above-mentioned dicyclopentadiene novolac type epoxy resin, include, for example EpiclonHP7200 (manufacture of DIC company) etc.
As the commercially available product in above-mentioned biphenyl phenolic resin varnish type epoxy resin, include, for example NC-3000P (Japanese chemical drug Inc. makes) etc.
As the commercially available product in 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 in 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 gas chemical company of Mitsubishi) etc.
As the commercially available product in abovementioned alkyl polyol type epoxy resin, include, for example: ZX-1542 (Nippon Steel lives aurification company and manufactures), Epiclon726 (manufacture of DIC company), Epolight80MFA (manufacture of chemical company of common prosperity society), DenacolEX-611 (manufacture of Nagasechemtex company) etc.
As the commercially available product in above-mentioned modified rubber type epoxy resin, include, for example: YR-450, YR-207 (be Nippon Steel and live the manufacture of aurification company), EpoleadPB (manufacture of Daicel company) etc.
As the commercially available product in above-mentioned epihydric alcohol ester compound, include, for example DenacolEX-147 (manufacture of Nagasechemtex company) etc.
As other the commercially available products in above-mentioned epoxy resin, include, for example: YDC-1312, YSLV-80XY, YSLV-90CR (be Nippon Steel and live the manufacture of aurification company), XAC4151 (Asahi Kasei Corporation's manufacture), jER1031, jER1032 (being Mitsubishi Chemical Ind to manufacture), EXA-7120 (manufacture of DIC company), TEPIC (manufacture of Nissan Chemical company) etc.
As the method manufacturing above-mentioned epoxy (methyl) acrylate, specifically, such as by while send into air and to resorcinol type epoxy resin (EX-201, Nagasechemtex company manufactures) 360 weight portions, p methoxy phenol 2 weight portion as polymerization inhibitor, triethylamine 2 weight portion as catalysts and acrylic acid 210 weight portion carry out return stirring, while make their reactions 5 hours at 90 DEG C, resorcinol type epoxy acrylate can be obtained thus.
As the commercially available product in above-mentioned epoxy (methyl) acrylate, include, for example: EBECRYL860, EBECRYL3200, EBECRYL3201, EBECRYL3412, EBECRYL3600, EBECRYL3700, EBECRYL3701, EBECRYL3702, EBECRYL3703, EBECRYL3800, EBECRYL6040, EBECRYLRDX63182 (being Daicel-Allnex company to manufacture), EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020 (being chemical industrial company of Xin Zhong village to manufacture), EpoxyEsterM-600A, EpoxyEster40EM, EpoxyEster70PA, EpoxyEster200PA, EpoxyEster80MFA, EpoxyEster3002M, EpoxyEster3002A, EpoxyEster1600A, EpoxyEster3000M, EpoxyEster3000A, EpoxyEster200EA, EpoxyEster400EA (being chemical company of common prosperity society to manufacture), DenacolAcrylateDA-141, DenacolAcrylateDA-314, DenacolAcrylateDA-911 (being Nagasechemtex company to manufacture) etc.
As carbamate (methyl) acrylate reacting above by (methyl) acrylic acid derivative and isocyanate compound that make to have hydroxyl and obtain, such as by relative to isocyanate compound 1 equivalent with 2 isocyanate group, (methyl) acrylic acid derivative 2 equivalent with hydroxyl is made to carry out reacting under the existence of the tin based compound of catalytic amount and obtain.
As the isocyanate compound of raw material becoming above-mentioned carbamate (methyl) acrylate, include, for example: isophorone diisocyanate, 2, 4-toluene diisocyanate, 2, 6-toluene diisocyanate, hexamethylene diisocyanate, trimethyl hexamethylene diisocyanate, diphenyl methane-4, 4 '-diisocyanate (MDI), hydrogenation MDI, aggretion type MDI, 1, 5-naphthalene diisocyanate, norbornene alkyl diisocyanate, tolidine diisocyanate, XDI (XDI), hydrogenation XDI, lysinediisocyanate, triphenylmethane triisocyanate, three (isocyanate phenyl) thiophosphate, tetramethylxylene diisocyanate, 1, 6, 11-undecane triisocyanate etc.
In addition, as the isocyanate compound of raw material becoming above-mentioned carbamate (methyl) acrylate, such as, can also use the isocyanate compound through chain elongation by making the polyvalent alcohol such as ethylene glycol, glycerine, D-sorbite, trimethylolpropane, (gathering) propylene glycol, carbonate diol, PTMEG, polyester-diol, polycaprolactone glycol and excessive isocyanate compound react and obtain.
As become above-mentioned carbamate (methyl) acrylate raw material, (methyl) acrylic acid derivative with hydroxyl, include, for example: the commercially available products such as (methyl) acrylic acid-2-hydroxyl ethyl ester, (methyl) acrylic acid 2-hydroxypropyl acrylate, (methyl) acrylic acid 4-hydroxy butyl ester, (methyl) acrylic acid 2-hydroxy butyl ester; List (methyl) acrylate of the dibasic alcohol such as ethylene glycol, propylene glycol, 1,3-PD, 1,3-BDO, BDO, polyglycol; List (methyl) acrylate of the trihydroxy alcohols such as trimethylolethane, trimethylolpropane, glycerine or two (methyl) acrylate; The epoxies such as bisphenol-a epoxy acrylate (methyl) acrylate etc.
Specifically, above-mentioned carbamate (methyl) acrylate such as obtains by such as under type: add trimethylolpropane 134 weight portion, the BHT0.2 weight portion as polymerization inhibitor, dibutyl tin laurate 0.01 weight portion as catalysts and isophorone diisocyanate 666 weight portion, while carry out return stirring at 60 DEG C, while make it reaction 2 hours, then, add acrylic acid 2-hydroxyl ethyl ester 51 weight portion, while carry out return stirring by sending into air, at 90 DEG C, make it reaction 2 hours.
As the commercially available product in above-mentioned carbamate (methyl) acrylate, include, for example: M-1100, M-1200, M-1210, M-1600 (being East Asia Synesis Company to manufacture), EBECRYL230, EBECRYL270, EBECRYL4858, EBECRYL8402, EBECRYL8804, EBECRYL8803, EBECRYL8807, EBECRYL9260, EBECRYL1290, EBECRYL5129, EBECRYL4842, EBECRYL210, EBECRYL4827, EBECRYL6700, EBECRYL220, EBECRYL2220 (being Daicel-Allnex company to manufacture), ArtresinUN-9000H, ArtresinUN-9000A, ArtresinUN-7100, ArtresinUN-1255, ArtresinUN-330, ArtresinUN-3320HB, ArtresinUN-1200TPK, ArtresinSH-500B (being Gen Shang industrial group 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 (being chemical industrial company of Xin Zhong village to manufacture), AH-600, AT-600, UA-306H, AI-600, UA-101T, UA-101I, UA-306T, UA-306I (being chemical company of common prosperity society to manufacture) etc.
For the object improving the cementability of sealing material for liquid crystal display device obtained, above-mentioned curable resin is also preferably containing epoxy resin.As above-mentioned epoxy resin, include, for example: become the epoxy resin of the raw material for the synthesis of above-mentioned epoxy (methyl) acrylate, partly (methyl) acrylic modified epoxy resin etc.
It should be noted that, in this manual, above-mentioned part (methyl) acrylic modified epoxy resin refers in 1 molecule the resin with epoxy radicals and each more than 1 of (methyl) acryloxy, such as, can obtain by making the epoxy radicals of a part for the epoxy resin of more than 2 and (methyl) acrylic acid react.
When sealing material for liquid crystal display device of the present invention contains above-mentioned epoxy resin, preferably coordinate above-mentioned (methyl) acrylic resin and above-mentioned epoxy resin in the mode making (methyl) acryloxy and the ratio of epoxy radicals become 30: 70 ~ 95: 5.If the ratio of (methyl) acryloxy is less than 30%, even if then the polymerization of (methyl) acryloxy terminates, still there is uncured epoxy resin ingredient in a large number, therefore sometimes produce liquid crystal pollution.If the ratio of (methyl) acryloxy is more than 95%, then sometimes obtained sealing material for liquid crystal display device becomes the sealant of cementability difference.
From the viewpoint of suppression liquid crystal pollution, above-mentioned curable resin preferably has-OH base ,-NH-base ,-NH
2the unit of the hydrogen bonds such as base.
In addition, consider from reactive height, above-mentioned (methyl) acrylic resin preferably has 2 ~ 3 (methyl) acryloxies in the molecule.
Sealing material for liquid crystal display device of the present invention can also contain hot radical polymerization initiator.
As above-mentioned hot radical polymerization initiator, include, for example the hot radical polymerization initiator be made up of azo-compound, organic peroxide etc.Wherein, the initiating agent (hereinafter also referred to as " polymeric azo initiating agent ") be preferably made up of polymeric azo compound.
It should be noted that, in this manual, polymeric azo initiating agent refers to: there is azo group and produced by heat the free radical that (methyl) acryloxy can be made to solidify, number-average molecular weight is the compound of more than 300.
The preferred lower limit of the number-average molecular weight of above-mentioned polymeric azo initiating agent is 1000, and the preferred upper limit is 300,000.If the number-average molecular weight of above-mentioned polymeric azo initiating agent is less than 1000, then harmful effect is carried out in polymeric azo initiating agent feeding crystal zone sometimes.If the number-average molecular weight of above-mentioned polymeric azo initiating agent is more than 300,000, then be sometimes difficult to be mixed in curable resin.More preferably the lower limit of the number-average molecular weight of above-mentioned polymeric azo initiating agent is 5000, and the preferred upper limit is 100,000, and further preferred lower limit is 10,000, and further preferred upper limit is 90,000.
It should be noted that, in this manual, above-mentioned number-average molecular weight is undertaken measuring and the value obtained by polystyrene conversion by gel permeation chromatography (GPC).As the pillar during number-average molecular weight measured by GPC based on polystyrene conversion, include, for example ShodexLF-804 (manufacture of Showa electrician company) etc.
As above-mentioned polymeric azo initiating agent, include, for example: the polymeric azo initiating agent with the structure being bonded with the unit such as multiple polyalkylene oxide, dimethyl silicone polymer by azo group.
As the above-mentioned polymeric azo initiating agent with the structure being bonded with the unit such as multiple polyalkylene oxides by azo group, preferably there is the polymeric azo initiating agent of polyethylene oxide structure.As such polymeric azo initiating agent, include, for example: 4, the condensed polymer, 4 of 4 '-azo two (4-cyanopentanoic acid) and poly alkylene glycol, 4 '-azo two (4-cyanopentanoic acid) and the condensed polymer etc. of dimethyl silicone polymer with terminal amino group, specifically, include, for example: VPE-0201, VPE-0401, VPE-0601, VPS-0501, VPS-1001 (the pure pharmaceutical worker's industry company with light that is manufactures) etc.
In addition, as the example of the azo-compound of on-macromolecular, can enumerate: V-65, V-501 (the pure pharmaceutical worker's industry company with light that is manufactures) etc.
As above-mentioned organic peroxide, include, for example: ketone peroxide, ketal peroxide, hydrogen peroxide, dialkyl peroxide, peroxyester, diacyl peroxide, peroxy dicarbonate etc.
About the content of above-mentioned hot radical polymerization initiator, relative to curable resin 100 weight portion, preferred lower limit is 0.05 weight portion, and the preferred upper limit is 10 weight portions.If the content of above-mentioned hot radical polymerization initiator is less than 0.05 weight portion, then the thermal polymerization of sometimes obtained sealing material for liquid crystal display device is not carried out fully.If the content of above-mentioned hot radical polymerization initiator is more than 10 weight portions, then sometimes produce liquid crystal pollution because of unreacted hot radical polymerization initiator.The preferred lower limit of the content of above-mentioned hot radical polymerization initiator is 0.1 weight portion, and the preferred upper limit is 5 weight portions.
Sealing material for liquid crystal display device of the present invention can also contain thermal curing agents.
As above-mentioned thermal curing agents, include, for example: organic acid hydrazides, imdazole derivatives, amines, polyhydric phenol based compound, acid anhydrides etc.Wherein, preferably organic acid hydrazides is used.
As above-mentioned organic acid hydrazides, include, for example: sebacic dihydrazide, isophthalic dihydrazide, adipic dihydrazide, acid dihydrazide etc.
As the commercially available product in above-mentioned organic acid hydrazides, include, for example: SDH, ADH (being great Zhong chemical company to manufacture), AmicureVDH, AmicureVDH-J, AmicureUDH, AmicureUDH-J (being AjinomotoFine-Techno company to manufacture) etc.
About the content of above-mentioned thermal curing agents, relative to above-mentioned curable resin 100 weight portion, preferred lower limit is 1 weight portion, and the preferred upper limit is 50 weight portions.If the content of above-mentioned thermal curing agents is less than 1 weight portion, then sometimes cannot make the heat curing fully of obtained sealing material for liquid crystal display device.If the content of above-mentioned thermal curing agents is more than 50 weight portions, then the viscosity of obtained sealing material for liquid crystal display device increases, and coating is deteriorated sometimes.The preferred upper limit of the content of above-mentioned thermal curing agents is 30 weight portions.
The objects such as the further raising of the raising for viscosity, the improvement based on the cementability of stress dispersion effect, the improvement of linear expansivity, the moisture-proof of solidfied material, sealing material for liquid crystal display device of the present invention is preferably containing filling agent.
As above-mentioned filling agent, include, for example: the inorganic fillers such as talcum, asbestos, silicon dioxide, zeyssatite, terre verte, bentonitic clay, calcium carbonate, magnesium carbonate, aluminium oxide, smectite, zinc paste, iron oxide, magnesium oxide, tin oxide, titanium dioxide, magnesium hydroxide, aluminium hydroxide, beaded glass, silicon nitride, barium sulphate, gypsum, calcium silicate, sericite atlapulgite, aluminium nitride; The organic fillers such as polyester micropartical, polyurethane particulate, polyvinyl particulate, acrylic polymers particulate.These filling agents can be used alone, and also can be used together two or more.
The preferred lower limit of the content of the above-mentioned filling agent in sealing material for liquid crystal display device 100 weight portion of the present invention is 10 weight portions, and the preferred upper limit is 70 weight portions.If the content of above-mentioned filling agent is less than 10 weight portions, then sometimes cannot play the effects such as the improvement of cementability fully.If the content of above-mentioned filling agent is more than 70 weight portions, then the viscosity of obtained sealing material for liquid crystal display device increases, and coating is deteriorated sometimes.The preferred lower limit of the content of above-mentioned filling agent is 20 weight portions, and the preferred upper limit is 60 weight portions.
Sealing material for liquid crystal display device of the present invention is preferably containing silane coupling agent.Above-mentioned silane coupling agent mainly has as the effect with the bonding auxiliary agent of substrate etc. of adhesive sealant well.
As above-mentioned silane coupling agent, from the viewpoint of improving with the excellent effect of the cementability of substrate etc., suppressing curable resin to the outflow in liquid crystal by carrying out chemical bonding with curable resin, such as, preferably use 3-TSL 8330,3-mercaptopropyi trimethoxy silane, 3-glycidoxypropyltrime,hoxysilane, 3-isocyanates propyl trimethoxy silicane etc.These silane coupling agents can be used alone, and also can be used together two or more.
The preferred lower limit of the content of the above-mentioned silane coupling agent in sealing material for liquid crystal display device 100 weight portion of the present invention is 0.1 weight portion, and the preferred upper limit is 10 weight portions.If the content of above-mentioned silane coupling agent is less than 0.1 weight portion, then sometimes cannot play the effect coordinating silane coupling agent to produce fully.If the content of above-mentioned silane coupling agent is more than 10 weight portions, then sometimes obtained sealing material for liquid crystal display device causes liquid crystal pollution.The preferred lower limit of the content of above-mentioned silane coupling agent is 0.3 weight portion, and the preferred upper limit is 5 weight portions.
Sealing material for liquid crystal display device of the present invention also can contain opacifier.By containing above-mentioned opacifier, sealing material for liquid crystal display device of the present invention can be suitable for being used as shading sealant.
As above-mentioned opacifier, include, for example: iron oxide, titanium are black, nigrosine, cyanine are black, fullerene, carbon black, resin-coated type carbon black etc.Wherein, preferred titanium is black.
Above-mentioned titanium is black, compared with the average transmittance of the light for wavelength 300 ~ 800nm, near ultraviolet range, material that particularly transmissivity of the light of wavelength 370 ~ 450nm is higher.That is, above-mentioned titanium is black is the opacifier with following character: by covering the light of the wavelength of visible region fully, and gives light-proofness to sealing material for liquid crystal display device of the present invention, on the other hand, makes the Transmission light of the wavelength near ultraviolet range.As the opacifier contained by sealing material for liquid crystal display device of the present invention, be preferably the material that insulativity is high, as the opacifier that insulativity is high, also preferably titanium is black.
For above-mentioned titanium is black, even if not surface treated titanium is black, also can play sufficient effect, but the black or covered titanium of inorganic constituents such as oxidized silicon, titanium dioxide, germanium oxide, aluminium oxide, zirconia, magnesium oxide of the titanium of the organic principle process such as surface coupling agent also can be used black etc. to have carried out surface-treated titanium black.Wherein, with the titanium of organic principle process black can improve further insulativity in preferred.
In addition, the liquid crystal display cells manufactured containing the black sealing material for liquid crystal display device of the present invention as opacifier of above-mentioned titanium is used to have sufficient light-proofness, so there is no spilling of light and there is high-contrast, the liquid crystal display cells with excellent display quality of image can be realized.
Commercially available product in black as above-mentioned titanium, include, for example: 12S, 13M, 13M-C, 13R-N, 14M-C (being MitsubishiMaterials company to manufacture), TilackD (red fringe changes into company and manufactures) etc.
The preferred lower limit of the specific surface area that above-mentioned titanium is black is 13m
2/ g, the preferred upper limit is 30m
2/ g, preferred lower limit is 15m
2/ g, the preferred upper limit are 25m
2/ g.
In addition, the preferred lower limit of the specific insulation that above-mentioned titanium is black is 0.5 Ω cm, and the preferred upper limit is 3 Ω cm, and preferred lower limit is 1 Ω cm, and the preferred upper limit is 2.5 Ω cm.
If below the distance between the substrate of the primary particle size liquid crystal display cells of above-mentioned opacifier, be not particularly limited, preferred lower limit is 1nm, and the preferred upper limit is 5 μm.If the primary particle size of above-mentioned opacifier is lower than 1nm, then viscosity, the thixotropy of obtained sealing material for liquid crystal display device significantly increase, and operability is deteriorated sometimes.If the primary particle size of above-mentioned opacifier is more than 5 μm, then sometimes obtained sealing material for liquid crystal display device is deteriorated to the coating of substrate.The preferred lower limit of the primary particle size of above-mentioned opacifier is 5nm, and the preferred upper limit is 200nm, and preferred lower limit is 10nm further, and the preferred upper limit is 100nm further.
The preferred lower limit of the content of the above-mentioned opacifier in sealing material for liquid crystal display device 100 weight portion of the present invention is 5 weight portions, and the preferred upper limit is 80 weight portions.If the content of above-mentioned opacifier is less than 5 weight portions, then sometimes cannot obtain sufficient light-proofness.If the content of above-mentioned opacifier is more than 80 weight portions, then sometimes obtained sealing material for liquid crystal display device reduces the intensity after the adhesion of substrate, solidification, or illustrative reduces.The preferred lower limit of the content of above-mentioned opacifier is 10 weight portions, and the preferred upper limit is 70 weight portions, and preferred lower limit is 30 weight portions further, and the preferred upper limit is 60 weight portions further.
As the method manufacturing sealing material for liquid crystal display device of the present invention, include, for example following method etc.: use the mixer such as homo dispenser, homogeneous mixer, universal mixer, planetary-type mixer, kneader, three-roller, by adjuvant mixing such as curable resin, thioxanthones system polymerization initiator, amine system sensitizer and the silane coupling agents that adds as required.
By coordinating electrically conductive microparticle in sealing material for liquid crystal display device of the present invention, thus upper and lower conductive material can be manufactured.This conductive material up and down containing sealing material for liquid crystal display device of the present invention and electrically conductive microparticle is also one of the present invention.
As above-mentioned electrically conductive microparticle, Metal Ball can be used, be formed with the particulate etc. of conductive metal layer on the surface of resin particle.Wherein, conduction can be carried out when not damaging transparency carrier etc. from the viewpoint of utilizing the elasticity of the excellence of resin particle and connect, preferably be formed with the particulate of conductive metal layer on the surface of resin particle.
Use sealing material for liquid crystal display device of the present invention or upper and lower conductive material of the present invention and the liquid crystal display cells manufactured also is one of the present invention.
As the method manufacturing liquid crystal display cells of the present invention, include, for example the method etc. with following operation: at ito thin film etc. with in a slice in 2 plate bases such as the glass substrate of electrode or PET substrate, make sealing material for liquid crystal display device of the present invention etc. form the operation of rectangular seal patterns by serigraphy, divider coating etc.; The tiny droplets of liquid crystal being dripped under the state that sealing material for liquid crystal display device of the present invention etc. is uncured is applied in the sealing frame of substrate, under vacuo the operation of another substrate overlapping; And to light such as the seal pattern partial illumination ultraviolets of sealing material for liquid crystal display device of the present invention etc., thus the operation making sealant temporary fixing; And the sealant having heated temporary fixing and make it the operation of main solidification.
Invention effect
According to the present invention, a kind of photo-curable can be provided excellent and the sealing material for liquid crystal display device of liquid crystal pollution can be suppressed.In addition, according to the present invention, can provide a kind of and use this sealing material for liquid crystal display device and the conductive material up and down made and liquid crystal display cells.
Embodiment
Following discloses embodiment illustrates in greater detail the present invention, but the present invention is not limited to these embodiments.
(embodiment 1 ~ 13, comparative example 1 ~ 5)
According to match ratio described in table 1,2, use planetary stirring machine (" the あ わ と り that Thinky company manufactures
taro ") by after each material mixing, use three-roller to mix further, prepare each sealing material for liquid crystal display device of embodiment 1 ~ 13, comparative example 1 ~ 5 thus.
< evaluates >
Following evaluation is carried out to each sealing material for liquid crystal display device obtained in embodiment and comparative example.Show the result in table 1,2.
(photo-curable)
The sealant being dispersed with sept particulate (" MicropearlSI-H050 " that ponding chemical industrial company manufactures) 1 weight portion in each sealing material for liquid crystal display device 100 weight portion obtained in embodiment and comparative example is coated glass substrate, the glass substrate of same size is made to be overlapped on this substrate, then, metal halide light irradiation 100mW/cm is used
2light 10 seconds, make photo-curable test film.Illumination injects row without the situation of cutoff filter and the 2 kinds of patterns of situation having 400nm cutoff filter, and makes 3 test films for each situation.Use infrared spectroscopy device (" FTS3000 " that BIORAD company manufactures), measure the variable quantity that front and back are penetrated in the illumination being derived from the peak of (methyl) acryloyl group, carry out the evaluation of photo-curable thus.Be evaluated as penetrating the situation of opisthogenesis from the peak of (methyl) acryloyl group minimizing more than 90% in illumination " ◎ "; opisthogenesis will be penetrated in illumination and reduce more than 80% from the peak of (methyl) acryloyl group and the situation being less than 90% is evaluated as "○"; opisthogenesis will be penetrated in illumination and reduce more than 70% from the peak of (methyl) acryloyl group and the situation being less than 80% is evaluated as " Δ ", and be evaluated as "×" by penetrating situation that the minimizing of opisthogenesis from the peak of (methyl) acryloyl group be less than 70% in illumination and evaluate photo-curable.
It should be noted that, the illumination being derived from the peak of (methyl) acryloyl group penetrate before and after change measure the mean value obtained by 3 test films.
(liquid crystal pollution)
Each sealing material for liquid crystal display device 100 weight portion sept particulate (ponding chemical industrial company manufacture " MicropearlSI-H050 ") 1 weight portion being scattered in embodiment and comparative example obtain and as sealing material for liquid crystal display device, the alignment films after 2 slice lappings (ラ PVC Application グ) and utilize divider to be coated with in the mode making the live width of sealant become 1mm with in a slice in the substrate of transparency electrode.
Then the tiny droplets of liquid crystal (Chisso company manufacture " JC-5004LA ") is dripped the substrate coated with transparency electrode sealant frame on whole, to fit immediately the colour filtering chip basic board of another sheet with transparency electrode, metal halide light irradiation 100mW/cm is used to sealant part
2ultraviolet 30 seconds and make it solidification, further with 120 DEG C of heating 1 hour and obtain liquid crystal display cells.Illumination injects row without the situation of cutoff filter and the 2 kinds of patterns of situation having 400nm cutoff filter, and makes 3 liquid crystal display cells for each situation.
For obtained liquid crystal display cells, by visual, liquid crystal pollution near sealant after becoming 1000 hours voltage applying states at 60 DEG C is confirmed.
Liquid crystal pollution is judged by the irregular colour of 3 liquid crystal display cells, according to the degree of irregular colour, about whole liquid crystal display cells, situation completely without irregular colour is evaluated as " ◎ ", the situation of irregular colour is slightly had to be evaluated as "○" at least 1 liquid crystal display cells, there is the situation of irregular colour to be slightly evaluated as " Δ " at least 1 liquid crystal display cells, have the situation of quite a lot of irregular colour to be evaluated as "×" at least 1 liquid crystal display cells and evaluate liquid crystal contaminative.
It should be noted that, be evaluated as " ◎ ", grade that the liquid crystal display cells of "○" is complete no problem in practical.
[table 1]
[table 2]
Utilizability in industry
According to the present invention, a kind of photo-curable can be provided excellent and the sealing material for liquid crystal display device of liquid crystal pollution can be suppressed.In addition, according to the present invention, can provide a kind of and use this sealing material for liquid crystal display device and the conductive material up and down made and liquid crystal display cells.
Claims (10)
1. a sealing material for liquid crystal display device, is characterized in that, containing the amine system sensitizer represented by curable resin, thioxanthones system polymerization initiator and following formula (1),
In formula (1), z represents the integer of more than 1, and P is the residue of (gathering) ethylene glycol, (gathering) propylene glycol, (gathering) butylene glycol, glycerine, trimethylolpropane, two (trihydroxy methyl) propane, pentaerythrite, dipentaerythritol or caprolactone polyol.
2. sealing material for liquid crystal display device as claimed in claim 1, is characterized in that, the residue of to be 2, P the be polyglycol of the z in formula (1).
3. sealing material for liquid crystal display device as claimed in claim 1 or 2, is characterized in that, the compound of thioxanthones system polymerization initiator represented by following formula (2),
In formula (2), n is 1 ~ 6, R
3for hydrogen atom, methyl or ethyl, when n is greater than 1, R
3represented group or atom can be the same or different; A expression-O-,-[O (CHR
2cHR
1)
a]
y-,-[O (CH
2)
bcO]
y-or ,-[O (CH
2)
bcO]
(y-1)-[O (CHR
2cHR
1)
a]-group, R
1and R
2in one represent hydrogen atom, another one represents hydrogen atom, methyl or ethyl, a is 1 ~ 2, b is 4 ~ 5, Q is the residue of (gathering) ethylene glycol, (gathering) propylene glycol, (gathering) butylene glycol, glycerine, trimethylolpropane, two (trihydroxy methyl) propane, pentaerythrite, dipentaerythritol or caprolactone polyol, free hydroxyl group in Q can be esterified, x is the number being greater than 1 and being no more than the hydroxyl value of Q, when x is greater than 1 and is no more than 2, y is 1 ~ 10, when x is more than 2, y is 3 ~ 10.
4. sealing material for liquid crystal display device as claimed in claim 3, it is characterized in that, the n in formula (2) is 1, R
3for hydrogen atom, A is the group of formula-O-.
5. the sealing material for liquid crystal display device as described in claim 3 or 4, is characterized in that, the Q in formula (2) is the residue of polytetramethylene glycol.
6. the sealing material for liquid crystal display device according to any one of claim 1 to 5, is characterized in that, the content of the amine system sensitizer represented by formula (1) in sealing material for liquid crystal display device 100 weight portion is 0.1 ~ 10 weight portion.
7. the sealing material for liquid crystal display device according to any one of claim 1 to 6, it is characterized in that, thioxanthones system polymerization initiator and the amine system sensitizer represented by formula (1) containing proportional with mass ratio range, be thioxanthones system polymerization initiator: amine system sensitizer=1 represented by formula (1): 0.05 ~ 1: 5.
8. the sealing material for liquid crystal display device according to any one of claim 1 to 7, is characterized in that, containing opacifier.
9. a conductive material about, is characterized in that, containing the sealing material for liquid crystal display device according to any one of claim 1 to 8 and electrically conductive microparticle.
10. a liquid crystal display cells, is characterized in that, uses the sealing material for liquid crystal display device according to any one of claim 1 to 8 or upper and lower conductive material according to claim 9 to manufacture.
Applications Claiming Priority (3)
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| JP2013-235158 | 2013-11-13 | ||
| JP2013235158 | 2013-11-13 | ||
| PCT/JP2014/079686 WO2015072416A1 (en) | 2013-11-13 | 2014-11-10 | Liquid-crystal-display-element sealant, vertical conductive material, and liquid-crystal display element |
Publications (2)
| Publication Number | Publication Date |
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| CN105339839A true CN105339839A (en) | 2016-02-17 |
| CN105339839B CN105339839B (en) | 2019-08-23 |
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| Country | Link |
|---|---|
| JP (1) | JP6460797B2 (en) |
| KR (1) | KR102255550B1 (en) |
| CN (1) | CN105339839B (en) |
| TW (1) | TWI643941B (en) |
| WO (1) | WO2015072416A1 (en) |
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|---|---|---|---|---|
| CN107603548A (en) * | 2017-09-14 | 2018-01-19 | 合肥惠科金扬科技有限公司 | A kind of liquid crystal sealing agent for TFT LCD displays |
| CN111742258A (en) * | 2018-10-26 | 2020-10-02 | 积水化学工业株式会社 | Sealing agent 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 |
|---|---|---|---|---|
| JP6197020B2 (en) * | 2015-12-17 | 2017-09-13 | 三井化学株式会社 | Photocurable resin composition, display element sealant, liquid crystal sealant, liquid crystal display panel, and method for producing the same |
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Also Published As
| Publication number | Publication date |
|---|---|
| JP6460797B2 (en) | 2019-01-30 |
| KR102255550B1 (en) | 2021-05-24 |
| TWI643941B (en) | 2018-12-11 |
| CN105339839B (en) | 2019-08-23 |
| WO2015072416A1 (en) | 2015-05-21 |
| KR20160085700A (en) | 2016-07-18 |
| JPWO2015072416A1 (en) | 2017-03-16 |
| TW201522594A (en) | 2015-06-16 |
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