WO2014014013A1 - 液晶シール剤及びそれを用いた液晶表示セル - Google Patents
液晶シール剤及びそれを用いた液晶表示セル Download PDFInfo
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- WO2014014013A1 WO2014014013A1 PCT/JP2013/069382 JP2013069382W WO2014014013A1 WO 2014014013 A1 WO2014014013 A1 WO 2014014013A1 JP 2013069382 W JP2013069382 W JP 2013069382W WO 2014014013 A1 WO2014014013 A1 WO 2014014013A1
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- WIPO (PCT)
- Prior art keywords
- liquid crystal
- epoxy resin
- dropping method
- liquid
- sealant
- Prior art date
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 208
- 239000000565 sealant Substances 0.000 title claims abstract description 66
- 238000000034 method Methods 0.000 claims abstract description 52
- 239000003999 initiator Substances 0.000 claims abstract description 15
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 9
- 239000003822 epoxy resin Substances 0.000 claims description 71
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- 239000003795 chemical substances by application Substances 0.000 claims description 51
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- 239000000758 substrate Substances 0.000 claims description 21
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- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000007870 radical polymerization initiator Substances 0.000 claims description 16
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- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 3
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- 239000005062 Polybutadiene Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
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- 229910052739 hydrogen Inorganic materials 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
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- 150000002791 naphthoquinones Chemical class 0.000 description 3
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- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 3
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- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
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- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 2
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- DRRZZMBHJXLZRS-UHFFFAOYSA-N n-[3-[dimethoxy(methyl)silyl]propyl]cyclohexanamine Chemical compound CO[Si](C)(OC)CCCNC1CCCCC1 DRRZZMBHJXLZRS-UHFFFAOYSA-N 0.000 description 1
- DAHPIMYBWVSMKQ-UHFFFAOYSA-N n-hydroxy-n-phenylnitrous amide Chemical class O=NN(O)C1=CC=CC=C1 DAHPIMYBWVSMKQ-UHFFFAOYSA-N 0.000 description 1
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- 239000010453 quartz Substances 0.000 description 1
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- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
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- 239000004576 sand Substances 0.000 description 1
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- 239000010703 silicon Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
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- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- UTADZBVVSYSYTG-UHFFFAOYSA-N tert-butyl(methyl)silane Chemical compound C[SiH2]C(C)(C)C UTADZBVVSYSYTG-UHFFFAOYSA-N 0.000 description 1
- WRWQRNWWCINRPO-UHFFFAOYSA-N tert-butyl-[2-[tert-butyl(dimethyl)silyl]oxy-1,1,2,2-tetraphenylethoxy]-dimethylsilane Chemical compound C(C)(C)(C)[Si](OC(C(C1=CC=CC=C1)(C1=CC=CC=C1)O[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1)(C)C WRWQRNWWCINRPO-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- JREYOWJEWZVAOR-UHFFFAOYSA-N triazanium;[3-methylbut-3-enoxy(oxido)phosphoryl] phosphate Chemical compound [NH4+].[NH4+].[NH4+].CC(=C)CCOP([O-])(=O)OP([O-])([O-])=O JREYOWJEWZVAOR-UHFFFAOYSA-N 0.000 description 1
- MPQVYFJXQMBTHQ-UHFFFAOYSA-N triethyl-(1,1,2,2-tetraphenyl-2-triethylsilyloxyethoxy)silane Chemical compound C(C)[Si](OC(C(C1=CC=CC=C1)(C1=CC=CC=C1)O[Si](CC)(CC)CC)(C1=CC=CC=C1)C1=CC=CC=C1)(CC)CC MPQVYFJXQMBTHQ-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-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
- 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
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/064—Polymers containing more than one epoxy group per molecule
-
- 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
- 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
- G02F1/1341—Filling or closing of cells
- G02F1/13415—Drop filling process
Definitions
- the liquid crystal sealant in an uncured state comes into contact with the liquid crystal. At that time, the components of the liquid crystal sealant are dissolved (eluting) in the liquid crystal to reduce the resistance value of the liquid crystal, There is a problem that a display defect occurs.
- the requirements for the cured product properties of the liquid crystal sealant itself, such as adhesive strength, are becoming stricter year by year. That is, in recent liquid crystal panels with a narrow frame design, the line width of the liquid crystal sealant is narrowed, and thus the problem of adhesive strength is more serious than before.
- the narrow line width of the liquid crystal sealant causes a problem that the upper and lower substrates peel off after normal temperature and humidity resistance reliability tests with the conventional adhesive strength. Therefore, development of a liquid crystal sealant for a liquid crystal dropping method having a low liquid crystal contamination property and a high adhesive strength has been carried out very vigorously.
- Patent Document 7 attention is paid to the photoinitiator, and an attempt is made to suppress dissolution of the photoinitiator in the liquid crystal. However, in view of the above situation, further improvements are required.
- liquid crystal sealant having excellent low liquid-contamination property and excellent cured product properties such as adhesive strength, although the development of the liquid crystal sealant has been carried out very vigorously. It has not been realized yet.
- the present invention relates to a liquid crystal sealant containing a photopolymerization initiator and a thermal radical polymerization initiator, and has excellent light-shielding part curability, thus reducing liquid crystal contamination under wiring and increasing the definition of a liquid crystal display element.
- Liquid crystal sealant for liquid crystal dropping method which enables high-speed response, low voltage drive, long life, and excellent cured properties such as adhesive strength, and liquid crystal display cell using the same is there.
- (meth) acryl means “acryl and / or methacryl”.
- thermosetting agent (e) is an organic acid hydrazide compound.
- a weir of the liquid crystal sealing agent for a liquid crystal dropping method according to any one of (1) to (10) formed on one substrate A method for producing a liquid crystal display cell, in which after the liquid crystal is dropped inside, the other substrate is bonded, and then the liquid crystal sealing agent for the liquid crystal dropping method is cured by ultraviolet rays and / or heat.
- the curing rate may be expressed as a gel fraction.
- This gel fraction is calculated from the mass ratio before and after immersion in acetone by immersing a test piece obtained by applying the liquid crystal sealant of the present invention with a thickness of 100 ⁇ m and irradiating with ultraviolet rays for 10 hours. That is, in the liquid crystal sealing agent of the present invention, the mass after acetone immersion is 60% or less of the mass before acetone immersion. A liquid crystal sealant having a gel fraction of 60% or less by ultraviolet irradiation exhibits a very high adhesive force after thermosetting. This result will be described in detail in Examples.
- the liquid crystal sealant of the present invention contains a photopolymerization initiator (a) and a thermal radical polymerization initiator (b).
- the photopolymerization initiator (a) is not particularly limited as long as it is a compound that generates radicals upon irradiation with ultraviolet rays or visible light and initiates a chain polymerization reaction.
- benzyldimethyl ketal 1-hydroxycyclohexyl phenyl ketone, diethyl Thioxanthone, benzophenone, 2-ethylanthraquinone, 2-hydroxy-2-methylpropiophenone, 2-methyl- [4- (methylthio) phenyl] -2-morpholino-1-propane, 2,4,6-trimethylbenzoyl
- Examples include diphenylphosphine oxide, camphorquinone, 9-fluorenone, diphenyl disulfide and the like.
- the superscript “RTM” means a registered trademark. From the viewpoint of liquid crystal contamination, it is preferable to use those having a (meth) acryl group in the molecule.
- 2-methacryloyloxyethyl isocyanate and 1- [4- (2-hydroxyethoxy) -phenyl]- The reaction product with 2-hydroxy-2methyl-1-propan-1-one is preferably used.
- This compound can be obtained by the method described in International Publication No. 2006/027982.
- organic peroxides include Kayamek RTM A, M, R, L, LH, SP-30C, Parkadox CH-50L, BC-FF, Kadox B-40ES, Parkadox 14, Trigonox RTM 22-70E, 23-C70, 121, 121-50E, 121-LS50E, 21-LS50E, 42, 42LS, Kayaester RTM P-70, TMPO-70, CND-C70, OO-50E, AN, Kayabutyl RTM B, Parkardox 16 , Kayacarbon RTM BIC-75, AIC-75 (above, manufactured by Kayaku Akzo Co., Ltd.), Permec RTM N, H, S, F, D, G, Perhexa RTM H, HC, Pat TMH, C, V, 22, MC, Pakyua RTM AH, AL, HB, Perbutyl RTM H, C, ND, L , Park Le RTM H, D, PEROYL RTM IB
- benzopinacol 1,2-dimethoxy-1,1,2,2-tetraphenylethane, 1,2-diethoxy-1,1,2,2-tetraphenylethane, 1,2-diphenoxy- 1,1,2,2-tetraphenylethane, 1,2-dimethoxy-1,1,2,2-tetra (4-methylphenyl) ethane, 1,2-diphenoxy-1,1,2,2-tetra (4-methoxyphenyl) ethane, 1,2-bis (trimethylsiloxy) -1,1,2,2-tetraphenylethane, 1,2-bis (triethylsiloxy) -1,1,2,2-tetraphenyl Ethane, 1,2-bis (t-butyldimethylsiloxy) -1,1,2,2-tetraphenylethane, 1-hydroxy-2-trimethylsiloxy-1,1,2,2-tetraphenylethane, 1- Examples include droxy-2-triethylsiloxy-1,1,2,2-tetrapheny
- the benzopinacol is commercially available from Tokyo Chemical Industry Co., Ltd., Wako Pure Chemical Industries, Ltd.
- a compound obtained by etherifying the hydroxy group of benzopinacol can be easily synthesized by a known method.
- a compound in which the hydroxy group of benzopinacol is converted to a silyl ether can be synthesized by a method in which the corresponding benzopinacol and various silylating agents are heated under a basic catalyst such as pyridine.
- the amount is less than 1.0 times mol, the reaction efficiency is poor and the reaction time is prolonged, so that thermal decomposition is promoted.
- the amount is more than 5.0 times mol, separation may be deteriorated during collection or purification may be difficult.
- the liquid crystal sealing agent of the present invention preferably further contains a (meth) acrylated epoxy resin (c), an epoxy resin (d), a thermosetting agent (e), and rubber fine particles (f).
- the (meth) acrylated epoxy resin (c) can be obtained by a known reaction between an epoxy resin and (meth) acrylic acid.
- the epoxy resin used as a raw material is not particularly limited, but a bifunctional or higher epoxy resin is preferable.
- resorcinol (resorcin) diglycidyl ether bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S Type epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy resin, bisphenol A novolac type epoxy resin, bisphenol F novolac type epoxy resin, alicyclic epoxy resin, aliphatic chain epoxy resin, glycidyl ester type epoxy resin, glycidyl Amine type epoxy resin, hydantoin type epoxy resin, isocyanurate type epoxy resin, phenol novolac type epoxy resin having triphenolmethane skeleton, other bifunctional phenol Diglycidyl ethers of Le acids, difunctional alcohols diglycidyl ethers of, and their halides, hydrogenated product and the like.
- bisphenol-type epoxy resin, novolac-type epoxy resin and diglycidyl ether of resorcinol (resorcin) are more preferable from the viewpoint of liquid crystal contamination.
- the content of the (meth) acrylated epoxy resin (c) is appropriately determined in consideration of the workability and physical properties of the liquid crystal sealant, and is usually about 25 to 80% by mass in the liquid crystal sealant, preferably 25. Is 75% by mass.
- the epoxy resin (d) is not particularly limited, but preferably has low contamination and solubility in the liquid crystal.
- suitable epoxy resins include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, diglycidyl ether of resorcinol (resorcin), phenol novolac type epoxy resin, cresol novolac type epoxy resin, bisphenol A Novolac type epoxy resin, bisphenol F novolac type epoxy resin, alicyclic epoxy resin, aliphatic chain epoxy resin, glycidyl ester type epoxy resin, glycidyl amine type epoxy resin, hydantoin type epoxy resin, isocyanurate type epoxy resin, triphenol Phenol novolac type epoxy resin having methane skeleton, diglycidyl etherified product of bifunctional phenols, diglycidyl ether of difunctional alcohols Products, and their halides, hydrogenated product and the like.
- the content of the epoxy resin (d) is appropriately determined in consideration of the workability and physical properties of the liquid crystal sealing agent, and is usually about 25 to 80% by mass, preferably 25 to 75% by mass in the liquid crystal sealing agent. is there. Moreover, it is one of the preferable aspects of this invention that an epoxy resin (d) occupies 70 mass% or more among the sum total of a (meth) acrylated epoxy resin (c) and an epoxy resin (d), and is 80 masses. % Is more preferable.
- thermosetting agent (e) means a thermosetting agent that does not generate radicals. Specifically, it reacts nucleophilically with an unshared electron pair or an anion in the molecule, and examples thereof include polyvalent amines, polyhydric phenols, and organic acid hydrazide compounds. However, it is not limited to these. Of these, organic acid hydrazide compounds are particularly preferably used.
- aromatic hydrazide terephthalic acid dihydrazide isophthalic acid dihydrazide, 2,6-naphthoic acid dihydrazide, 2,6-pyridinedihydrazide, 1,2,4-benzenetrihydrazide, 1,4,5,8-naphthoic acid
- aromatic hydrazide terephthalic acid dihydrazide isophthalic acid dihydrazide
- 2,6-naphthoic acid dihydrazide 2,6-pyridinedihydrazide
- 1,2,4-benzenetrihydrazide 1,4,5,8-naphthoic acid
- tetrahydrazide and pyromellitic acid tetrahydrazide examples include tetrahydrazide and pyromellitic acid tetrahydrazide.
- aliphatic hydrazide compounds include form hydrazide, acetohydrazide, propionic acid hydrazide, oxalic acid dihydrazide, malonic acid dihydrazide, succinic acid dihydrazide, glutaric acid dihydrazide, adipic acid dihydrazide, pimelic acid dihydrazide, sebacic acid dihydrazide.
- Examples of the compound having an isocyanuric acid skeleton include tris (1-hydrazinocarbonylmethyl) isocyanurate, tris (2-hydrazinocarbonylethyl) isocyanurate, tris (3-hydrazinocarbonylpropyl) isocyanurate, bis (2- Hydrazinocarbonylethyl) isocyanurate and the like.
- thermosetting agent (e) the content is 1 to 20 parts by mass when the total amount of the (meth) acrylated epoxy resin (c) and the epoxy resin (d) is 100 parts by mass.
- the content is preferably 2 to 15 parts by mass, and two or more kinds may be mixed and used.
- the rubber fine particles (f) include, for example, natural rubber (NR), isoprene rubber (IR), butadiene rubber (BR), styrene / butadiene rubber (SBR), butyl rubber (IIR), nitrile rubber (NBR), ethylene / propylene rubber ( EPM, EP), chloroprene rubber (CR), acrylic rubber (ACM, ANM), chlorosulfonated polyethylene rubber (CSM), urethane rubber (PUR), silicone rubber (Si, SR), fluoro rubber (FKM, FPM), Polysulfide rubber (thiocol) and the like may be mentioned, and single rubber fine particles may be used, or a core-shell structure may be used by using two or more kinds. Two or more kinds may be used in combination. Of these, acrylic rubber and silicone rubber are preferable.
- the acrylic rubber is preferably a core-shell structure acrylic rubber composed of two types of acrylic rubbers, and in particular, the core layer is preferably n-butyl acrylate and the shell layer is methyl methacrylate.
- the core layer is preferably n-butyl acrylate and the shell layer is methyl methacrylate.
- Zefiac RTM F-351 sold by Aika Industries Co., Ltd. as Zefiac RTM F-351.
- examples of the silicone rubber include organopolysiloxane crosslinked product powder and linear dimethylpolysiloxane crosslinked product powder.
- examples of the composite silicone rubber include those obtained by coating the silicone rubber surface with a silicone resin (for example, polyorganosilsesquioxane resin).
- a silicone rubber of a linear dimethylpolysiloxane crosslinked powder or a composite silicone rubber fine particle of a silicone resin-coated linear dimethylpolysiloxane crosslinked powder is particularly preferable. These may be used alone or in combination of two or more.
- the rubber powder has a spherical shape with little viscosity increase after addition.
- the true specific gravity of the silicone rubber powder is preferably 0.9 to 1.1. When the true specific gravity is larger than 1.1, the rubber particles become hard, and a gap formation is hindered when the upper and lower glass substrates are bonded together during the production of the liquid crystal cell.
- the average particle size of the silicone rubber powder is preferably 4 to 9 ⁇ m. When the average particle size is larger than 9 ⁇ m, the cell gap is not easily crushed. When the average particle size is smaller than 4 ⁇ m, liquid crystal seal puncture is likely to occur during cell formation.
- the JIS-A rubber hardness of the silicone rubber powder is measured with a durometer, but is preferably 10 to 50. If the JIS-A rubber hardness is greater than 50, it is too hard to make the cell gap difficult to collapse. If the JIS-A rubber hardness is less than 10, liquid crystal seal puncture is likely to occur during cell formation.
- the average particle size of the composite silicone rubber powder is preferably 1 to 9 ⁇ m. When the average particle size is larger than 9 ⁇ m, the cell gap is not easily crushed. If the average particle size is smaller than 1 ⁇ m, liquid crystal seal puncture is likely to occur during cell formation.
- the JIS-A rubber hardness of the composite silicone rubber powder is measured with a durometer, but is preferably 10 to 90. If the JIS-A rubber hardness is greater than 90, it is too hard to make the cell gap difficult to collapse. If the JIS-A rubber hardness is less than 10, liquid crystal seal puncture is likely to occur during cell formation.
- the content of the rubber fine particles (f) in the liquid crystal sealant is 2 to 20% by mass, preferably 5 to 15% by mass. If the content is too small, a seal puncture occurs due to a decrease in the viscosity of the liquid crystal sealant during heating during liquid crystal cell production, and the liquid crystal leaks. When there is too much content, the viscosity of a liquid-crystal sealing compound will become high too much, and it will become impossible to apply
- the silane coupling agent (g) can be used to improve the adhesive strength and the moisture resistance reliability.
- Silane coupling agents include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltri Methoxysilane, N-phenyl- ⁇ -aminopropyltrimethoxysilane, N- (2-aminoethyl) 3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) 3-aminopropylmethyltrimethoxysilane, 3- Aminopropyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, vinyltrimethoxysilane, N- (2- (vinylbenzylamino) ethyl) 3-
- silane coupling agents are sold by Shin-Etsu Chemical Co., Ltd. as KBM series, KBE series, etc., they are easily available from the market.
- the content of the silane coupling agent (g) in the liquid crystal sealant is preferably 0.05 to 3% by mass when the total liquid crystal sealant of the present invention is 100% by mass.
- naphthoquinone 2-hydroxynaphthoquinone, 2-methylnaphthoquinone, 2-methoxynaphthoquinone, 2,2,6,6, -tetramethylpiperidine-1-oxyl, 2,2,6,6, -tetramethyl -4-hydroxypiperidine-1-oxyl, 2,2,6,6, -tetramethyl-4-methoxypiperidine-1-oxyl, 2,2,6,6, -tetramethyl-4-phenoxypiperidine-1- Oxyl, hydroquinone, 2-methylhydroquinone, 2-methoxyhydroquinone, parabenzoquinone, butylated hydroxyanisole, 2,6-di-t-butyl-4-ethylphenol, 2,6-di-t-butylcresol, stearyl ⁇ -(3,5-di-t-butyl-4-hydroxyphenyl) propionate, 2,2'-methylene (4-ethyl-6-tert-
- naphthoquinone, hydroquinone, and nitroso piperazine radical polymerization inhibitors are preferred, and naphthoquinone, 2-hydroxynaphthoquinone, hydroquinone, 2,6-di-tert-butyl-P-cresol, polystop 7300P (Hakuto Co., Ltd.) Company-made) is more preferred, and Polystop 7300P (made by Hakuto Co., Ltd.) is most preferred.
- the radical polymerization inhibitor (h) is added to the method of synthesizing the (meth) acrylated epoxy resin (c), the (meth) acrylated epoxy resin (c) and / or the epoxy resin (d).
- an inorganic filler can be used to improve adhesive strength and moisture resistance reliability.
- this inorganic filler fused silica, crystalline silica, silicon carbide, silicon nitride, boron nitride, calcium carbonate, magnesium carbonate, barium sulfate, calcium sulfate, mica, talc, clay, alumina, magnesium oxide, zirconium oxide, aluminum hydroxide , Magnesium hydroxide, calcium silicate, aluminum silicate, lithium aluminum silicate, zirconium silicate, barium titanate, glass fiber, carbon fiber, molybdenum disulfide, asbestos, etc., preferably fused silica, crystalline silica, silicon nitride, nitriding Boron, calcium carbonate, barium sulfate, calcium sulfate, mica, talc, clay, alumina, aluminum hydroxide, calcium silicate, aluminum silicate, more preferably fused silica,
- the particle size can be measured with a laser diffraction / scattering particle size distribution analyzer (dry type) (manufactured by Seishin Enterprise Co., Ltd .; LMS-30).
- the content when an inorganic filler is used is usually 10 to 60% by mass, preferably 20 to 50% by mass, based on 100% by mass of the entire liquid crystal sealant.
- the content of the inorganic filler is lower than 5% by mass, the adhesive strength to the glass substrate is lowered, and the moisture resistance reliability is inferior, so that the decrease in the adhesive strength after moisture absorption may be increased.
- the content of the inorganic filler is more than 60% by mass, the filler content is too large, so that it may be difficult to be crushed and the liquid crystal cell gap may not be formed.
- a monomer and / or oligomer of (meth) acrylic acid ester may be used as necessary.
- Such monomers and oligomers include, for example, a reaction product of dipentaerythritol and (meth) acrylic acid, a reaction product of dipentaerythritol / caprolactone and (meth) acrylic acid, etc., but has a contamination property to liquid crystals. If it is low, it will not be restricted in particular.
- the liquid crystal sealant of the present invention may further contain additives such as curing accelerators such as organic acids and imidazoles, organic fillers, pigments, leveling agents, antifoaming agents, solvents and the like, if necessary.
- curing accelerators such as organic acids and imidazoles
- organic fillers such as organic fillers, pigments, leveling agents, antifoaming agents, solvents and the like, if necessary.
- the liquid crystal is dropped inside the weir made of the liquid crystal sealant, and the other glass substrate is overlaid in a vacuum, and a gap is created. After the gap is formed, the liquid crystal sealant is irradiated with ultraviolet rays by an ultraviolet irradiator and photocured.
- the amount of ultraviolet irradiation is preferably 500 to 6000 mJ / cm 2 , more preferably 1000 to 4000 mJ / cm 2 .
- the liquid crystal display cell of the present invention can be obtained by curing at 90 to 130 ° C. for 1 to 2 hours.
- the liquid crystal sealing agent of Comparative Examples 1 and 2 was prepared by blending the materials shown in Table 1 by the same process.
- cure at 120 degreeC for 1 hour was measured by the above-mentioned method. The results are shown in Table 1.
- the liquid crystal sealants of Examples 1 to 3 have very high adhesive strength both in the case of curing using ultraviolet rays and heat as well as in the case of curing only with heat, and are superior in comparison with the past. It was confirmed that it had characteristics. Therefore, it can be said that the liquid crystal sealing agent of the present invention can realize long-term high reliability of the liquid crystal display cell.
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- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nonlinear Science (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Mathematical Physics (AREA)
- Sealing Material Composition (AREA)
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- Macromonomer-Based Addition Polymer (AREA)
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| CN201380037836.2A CN104471471A (zh) | 2012-07-17 | 2013-07-17 | 液晶密封剂及使用它的液晶显示单元 |
| KR1020157002690A KR20150032885A (ko) | 2012-07-17 | 2013-07-17 | 액정 시일제 및 그것을 사용한 액정 표시 셀 |
| JP2014525839A JPWO2014014013A1 (ja) | 2012-07-17 | 2013-07-17 | 液晶シール剤及びそれを用いた液晶表示セル |
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| JP2012-158479 | 2012-07-17 | ||
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| WO2014014013A1 true WO2014014013A1 (ja) | 2014-01-23 |
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| KR (1) | KR20150032885A (zh) |
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| WO (1) | WO2014014013A1 (zh) |
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| CN104312477A (zh) * | 2014-10-31 | 2015-01-28 | 合肥鑫晟光电科技有限公司 | 封框胶组合物及显示装置 |
| CN104650761A (zh) * | 2015-02-06 | 2015-05-27 | 深圳广恒威科技有限公司 | 用于汽车电子模块的耐高温杂合类导电胶及其制备方法 |
| JP2015215514A (ja) * | 2014-05-12 | 2015-12-03 | 協立化学産業株式会社 | 液晶表示素子用シール剤 |
| JP2016095511A (ja) * | 2014-11-07 | 2016-05-26 | 積水化学工業株式会社 | 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子 |
| JP2016218447A (ja) * | 2015-05-25 | 2016-12-22 | 積水化学工業株式会社 | 液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子 |
| JP2017026736A (ja) * | 2015-07-21 | 2017-02-02 | 日本化薬株式会社 | 液晶シール剤及びそれを用いた液晶表示セル |
| JP2017027041A (ja) * | 2015-07-21 | 2017-02-02 | 日本化薬株式会社 | 液晶シール剤及びそれを用いた液晶表示セル |
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| CN106370616A (zh) * | 2016-11-09 | 2017-02-01 | 深圳市华星光电技术有限公司 | 框胶固化率测试样品的制备方法及框胶固化率测试方法 |
| CN109196413B (zh) * | 2016-12-27 | 2021-03-16 | 积水化学工业株式会社 | 液晶显示元件用密封剂、上下导通材料和液晶显示元件 |
| KR20220123426A (ko) * | 2020-02-06 | 2022-09-06 | 미쓰이 가가쿠 가부시키가이샤 | 광열경화성 수지 조성물 및 이것을 포함하는 액정 실링제, 및 액정 표시 패널 및 그의 제조 방법 |
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| WO2011061910A1 (ja) * | 2009-11-17 | 2011-05-26 | 日本化薬株式会社 | 新規熱ラジカル発生剤、その製造方法、液晶シール剤及び液晶表示セル |
| JP2011197654A (ja) * | 2010-02-26 | 2011-10-06 | Sekisui Chem Co Ltd | 液晶滴下工法用シール剤、及び、上下導通材料、及び、液晶表示素子 |
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| US5898041A (en) * | 1995-03-01 | 1999-04-27 | Matsushita Electric Industrial Co., Ltd. | Production process of liquid crystal display panel, seal material for liquid crystal cell and liquid crystal display |
| AU2003264513A1 (en) * | 2002-09-19 | 2004-04-08 | Mitsui Chemicals, Inc. | Sealing composition for liquid crystal displays and process for production of liquid crystal display panels |
| CN101867024B (zh) * | 2010-06-01 | 2011-10-05 | 友达光电股份有限公司 | 封装方法 |
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| WO2011061910A1 (ja) * | 2009-11-17 | 2011-05-26 | 日本化薬株式会社 | 新規熱ラジカル発生剤、その製造方法、液晶シール剤及び液晶表示セル |
| JP2011197654A (ja) * | 2010-02-26 | 2011-10-06 | Sekisui Chem Co Ltd | 液晶滴下工法用シール剤、及び、上下導通材料、及び、液晶表示素子 |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015215514A (ja) * | 2014-05-12 | 2015-12-03 | 協立化学産業株式会社 | 液晶表示素子用シール剤 |
| CN104312477A (zh) * | 2014-10-31 | 2015-01-28 | 合肥鑫晟光电科技有限公司 | 封框胶组合物及显示装置 |
| JP2016095511A (ja) * | 2014-11-07 | 2016-05-26 | 積水化学工業株式会社 | 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子 |
| CN104650761A (zh) * | 2015-02-06 | 2015-05-27 | 深圳广恒威科技有限公司 | 用于汽车电子模块的耐高温杂合类导电胶及其制备方法 |
| JP2016218447A (ja) * | 2015-05-25 | 2016-12-22 | 積水化学工業株式会社 | 液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子 |
| JP2017026736A (ja) * | 2015-07-21 | 2017-02-02 | 日本化薬株式会社 | 液晶シール剤及びそれを用いた液晶表示セル |
| JP2017027041A (ja) * | 2015-07-21 | 2017-02-02 | 日本化薬株式会社 | 液晶シール剤及びそれを用いた液晶表示セル |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20150032885A (ko) | 2015-03-30 |
| TW201420736A (zh) | 2014-06-01 |
| CN104471471A (zh) | 2015-03-25 |
| JPWO2014014013A1 (ja) | 2016-07-07 |
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