CN113874462B - Sealing agent for liquid crystal display element, vertically conductive material, and liquid crystal display element - Google Patents
Sealing agent for liquid crystal display element, vertically conductive material, and liquid crystal display element Download PDFInfo
- Publication number
- CN113874462B CN113874462B CN202080037785.3A CN202080037785A CN113874462B CN 113874462 B CN113874462 B CN 113874462B CN 202080037785 A CN202080037785 A CN 202080037785A CN 113874462 B CN113874462 B CN 113874462B
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- China
- Prior art keywords
- liquid crystal
- crystal display
- display element
- meth
- acrylate
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 155
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 49
- 239000004020 conductor Substances 0.000 title claims description 9
- 238000007789 sealing Methods 0.000 title abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 100
- 239000000565 sealant Substances 0.000 claims abstract description 87
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 25
- 229920005989 resin Polymers 0.000 claims abstract description 21
- 239000011347 resin Substances 0.000 claims abstract description 21
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 239000007870 radical polymerization initiator Substances 0.000 claims description 16
- 239000010419 fine particle Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000001029 thermal curing Methods 0.000 claims 1
- 238000011109 contamination Methods 0.000 abstract description 20
- 238000003860 storage Methods 0.000 abstract description 20
- 239000000463 material Substances 0.000 abstract description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 108
- -1 amine compounds Chemical class 0.000 description 53
- 239000003822 epoxy resin Substances 0.000 description 45
- 229920000647 polyepoxide Polymers 0.000 description 45
- 239000004593 Epoxy Substances 0.000 description 38
- 239000000126 substance Substances 0.000 description 33
- 239000000047 product Substances 0.000 description 29
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 22
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- 238000000034 method Methods 0.000 description 20
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- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 15
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- 239000000758 substrate Substances 0.000 description 14
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- 238000003786 synthesis reaction Methods 0.000 description 13
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- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
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- 239000006087 Silane Coupling Agent Substances 0.000 description 8
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- LOCXTTRLSIDGPS-FVDSYPCUSA-N [(z)-[1-oxo-1-(4-phenylsulfanylphenyl)octan-2-ylidene]amino] benzoate Chemical compound C=1C=C(SC=2C=CC=CC=2)C=CC=1C(=O)C(/CCCCCC)=N\OC(=O)C1=CC=CC=C1 LOCXTTRLSIDGPS-FVDSYPCUSA-N 0.000 description 1
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- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
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- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- JGCWKVKYRNXTMD-UHFFFAOYSA-N bicyclo[2.2.1]heptane;isocyanic acid Chemical compound N=C=O.N=C=O.C1CC2CCC1C2 JGCWKVKYRNXTMD-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
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- 239000003054 catalyst Substances 0.000 description 1
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- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
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- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
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- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 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
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
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- 238000010828 elution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
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- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 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
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- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
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- 150000003949 imides Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 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
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury 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
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
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- 239000003605 opacifier Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
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- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000004513 sizing Methods 0.000 description 1
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- 239000000600 sorbitol 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
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- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 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
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- IKXFIBBKEARMLL-UHFFFAOYSA-N triphenoxy(sulfanylidene)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=S)OC1=CC=CC=C1 IKXFIBBKEARMLL-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
- C09J163/10—Epoxy resins modified by unsaturated compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C08L25/08—Copolymers of styrene
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
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Abstract
The purpose of the present invention is to provide a sealing agent for a liquid crystal display element, which has excellent storage stability, adhesion and low liquid crystal contamination. The present invention also provides a vertical conduction material and a liquid crystal display element using the sealant for a liquid crystal display element. The present invention provides a sealant for a liquid crystal display element, which contains a curable resin and a thermosetting agent, wherein the thermosetting agent contains a hydrazide compound having a structure represented by the following formula (1-1) and a structure represented by the following formula (1-2). Ar in the formula (1-1) is an aromatic ring, and R 1 in the formula (1-2) is a hydrogen atom or a methyl group.
Description
Technical Field
The present invention relates to a sealant for a liquid crystal display element, which is excellent in storage stability, adhesiveness, and low liquid crystal contamination. The present invention also relates to a vertical conduction material and a liquid crystal display element using the sealant for a liquid crystal display element.
Background
In recent years, as a method for manufacturing a liquid crystal display element such as a liquid crystal display cell, a liquid crystal dropping method called a dropping method using a sealant as disclosed in patent document 1 and patent document 2 has been used in view of shortening a tact time and optimizing a liquid crystal usage amount.
In the dropping process, first, a frame-shaped seal pattern is formed on one of two substrates with electrodes by dispensing. Next, a liquid crystal display element was fabricated by dropping a droplet of liquid crystal into a frame of a seal pattern in a state where the sealant was not cured, and then, by superposing another substrate under vacuum, curing the sealant. The dropping process is now the main stream of the method for manufacturing liquid crystal display elements.
However, in modern times, in which various mobile devices with liquid crystal panels such as mobile phones and portable game machines are used, the most important problem is miniaturization of the devices. As a method for downsizing the device, for example, a liquid crystal display portion is narrowed, and a sealing portion is arranged below a black matrix (hereinafter, also referred to as a narrow frame design).
However, since the sealant is disposed directly under the black matrix in the narrow frame design, the light irradiated when the sealant is photo-cured is blocked by the dropping process, and the light does not easily reach the inside of the sealant, and thus curing is insufficient in the conventional sealant. In this way, if the curing of the sealant is insufficient, uncured sealant components are eluted into the liquid crystal, and there is a problem in that liquid crystal contamination is likely to occur. In particular, in recent years, with the increase in polarity of liquid crystals, a further low liquid crystal contamination property has been demanded for a sealant.
In the case where it is difficult to photocure the sealant, it is considered to be cured by heating, and as a method for curing the sealant by heating, an operation of blending a thermosetting agent into the sealant is performed. However, when a thermosetting agent having high reactivity is used to improve curability and adhesiveness of the sealant, the storage stability of the resulting sealant may be deteriorated.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 2001-133794
Patent document 2: international publication No. 02/092718
Disclosure of Invention
Problems to be solved by the invention
The purpose of the present invention is to provide a sealing agent for a liquid crystal display element, which has excellent storage stability, adhesion and low liquid crystal contamination. The present invention also provides a vertical conduction material and a liquid crystal display element using the sealant for a liquid crystal display element.
Means for solving the problems
The present invention provides a sealant for a liquid crystal display element, comprising a curable resin and a thermosetting agent, wherein the thermosetting agent comprises a hydrazide compound having a structure represented by the following formula (1-1) and a structure represented by the following formula (1-2).
[ Chemical 1]
Ar in the formula (1-1) is an aromatic ring, and R 1 in the formula (1-2) is a hydrogen atom or a methyl group.
The present invention will be described in detail below.
The inventors have conducted intensive studies and as a result found that: the use of a thermosetting agent having a specific structure can provide a sealant for a liquid crystal display element excellent in storage stability, adhesiveness, and low liquid crystal contamination, and thus the present invention has been completed.
The sealant for a liquid crystal display element of the present invention contains a thermosetting agent.
The above-mentioned thermosetting agent contains a hydrazide compound.
The hydrazide compound has a structure represented by the above formula (1-1) and a structure represented by the above formula (1-2). Hereinafter, the hydrazide compound having the structure represented by the above formula (1-1) and the structure represented by the above formula (1-2) is also referred to as "the hydrazide compound of the present invention". By containing the hydrazide compound of the present invention, the sealant for a liquid crystal display element of the present invention is excellent in all of storage stability, adhesiveness, and low liquid crystal contamination.
The reason why the use of the hydrazide compound of the present invention gives a sealant for a liquid crystal display element excellent in all of storage stability, adhesiveness, and low liquid crystal contamination is considered as follows.
Namely, consider that: by having the structure represented by the above formula (1-1), the softening point of the hydrazide compound can be controlled, and thus the storage stability can be improved. In addition, it can be considered that: by having the structure represented by the above formula (1-2) containing a primary amino group, the adhesiveness of the resulting sealant can be improved. Furthermore, it can be considered that: by having these structures, the molecular weight of the hydrazide compound is increased, and thus elution into the liquid crystal can be suppressed.
In the hydrazide compound of the present invention, the preferable lower limit of the proportion of the structure represented by the above formula (1-1) is 5 mol%, and the preferable upper limit is 95 mol%. When the proportion of the structure represented by the above formula (1-1) is 5 mol% or more, the resulting sealant for a liquid crystal display element is more excellent in storage stability. When the proportion of the structure represented by the above formula (1-1) is 95 mol% or less, the resulting sealant for a liquid crystal display element is more excellent in adhesion. The ratio of the structure represented by the above formula (1-1) is more preferably 10 mol% at the lower limit, 90 mol% at the upper limit, and 50 mol% at the upper limit.
In the hydrazide compound of the present invention, the preferable lower limit of the proportion of the structure represented by the above formula (1-2) is 5 mol%, and the preferable upper limit is 95 mol%. When the proportion of the structure represented by the above formula (1-2) is 5 mol% or more, the resulting sealant for a liquid crystal display element is more excellent in adhesion. When the proportion of the structure represented by the above formula (1-2) is 95 mol% or less, the resulting sealant for a liquid crystal display element is more excellent in storage stability. The ratio of the structure represented by the above formula (1-2) is more preferably 10 mol% at the lower limit, 90 mol% at the upper limit, and 50 mol% at the lower limit.
The hydrazide compound of the present invention may have a structure other than the structure represented by the above formula (1-1) and the structure represented by the above formula (1-2).
The hydrazide compound of the present invention preferably has a structure represented by the following formula (2) as the other structure. The sealing agent for a liquid crystal display element obtained by the structure shown in the following formula (2) has more excellent adhesion.
[ Chemical 2]
In the formula (2), R 2 is a hydrogen atom OR a methyl group, R 3 is a-C (=o) OR 4 group (R 4 is a hydrogen atom OR an alkyl group having 1 to 10 carbon atoms), a-CN group, a-OR 5 group (R 5 is an alkyl group having 1 to 10 carbon atoms), OR a hydrogen atom.
The preferred lower limit of the weight average molecular weight of the hydrazide compound of the present invention is 2000, and the preferred upper limit is 20 ten thousand. The sealing agent for a liquid crystal display element obtained by setting the weight average molecular weight to 2000 or more is more excellent in low liquid crystal contamination. The sealing agent for a liquid crystal display element obtained by setting the weight average molecular weight to 20 ten thousand or less is more excellent in handling property. The lower limit of the weight average molecular weight is more preferably 4000, and the upper limit is more preferably 10 ten thousand.
In the present specification, the weight average molecular weight is a value obtained by measuring by Gel Permeation Chromatography (GPC) using tetrahydrofuran as a solvent and converting the obtained product into polystyrene. Examples of the column used for measuring the weight average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa electric company).
The preferred lower limit of the softening point of the hydrazide compound of the present invention is 65℃and the preferred upper limit is 200 ℃. The sealing agent for a liquid crystal display element obtained by setting the softening point of the hydrazide compound of the present invention to 65 ℃ or higher is more excellent in storage stability. The sealing agent for a liquid crystal display element obtained by setting the softening point of the hydrazide compound of the present invention to 200 ℃ or lower is more excellent in adhesion. The more preferable lower limit of the softening point of the hydrazide compound of the present invention is 90℃and the more preferable upper limit is 160 ℃.
The softening point can be obtained by the ring and ball method according to JIS K2207.
Examples of the method for producing the hydrazide compound of the present invention include the following methods.
That is, first, a compound represented by the following formula (3-1) and a compound represented by the following formula (3-2) are dissolved in a solvent such as tetrahydrofuran, and the reaction is performed by heating and stirring the mixture while nitrogen substitution is performed in the presence of a polymerization initiator such as azobisisobutyronitrile. The obtained reaction product was concentrated and reprecipitated in an ethanol solution to obtain an intermediate polymer compound. The intermediate polymer compound and hydrazine hydrate obtained are dissolved in a solvent such as tetrahydrofuran, and reacted under reflux. After the completion of the reaction, the solid component is separated by concentration, whereby the hydrazide compound of the present invention can be obtained.
In addition, in addition to the compound represented by the following formula (3-1) and the compound represented by the following formula (3-2), a compound represented by the following formula (4) may be used.
[ Chemical 3]
Ar in the formula (3-1) is an aromatic ring, R 1 in the formula (3-2) is a hydrogen atom or a methyl group, and R 6 is an alkyl group having 1 to 10 carbon atoms.
[ Chemical 4]
In the formula (4), R 2 is a hydrogen atom OR a methyl group, R 3 is a-C (=o) OR 4 group (R 4 is a hydrogen atom OR an alkyl group having 1 to 10 carbon atoms), a-CN group, a-OR 5 group (R 5 is an alkyl group having 1 to 10 carbon atoms), OR a hydrogen atom.
The content of the hydrazide compound of the present invention is preferably 1 part by weight at the lower limit and 20 parts by weight at the upper limit, based on 100 parts by weight of the curable resin. When the content of the hydrazide compound of the present invention is 1 part by weight or more, the resulting sealant for a liquid crystal display element is more excellent in curability and adhesiveness. When the content of the hydrazide compound of the present invention is 20 parts by weight or less, the resulting sealant for a liquid crystal display element is more excellent in storage stability and low liquid crystal contamination. The more preferable lower limit of the content of the hydrazide compound of the present invention is 2 parts by weight, and the more preferable upper limit is 15 parts by weight.
The sealant for a liquid crystal display element of the present invention may contain a thermosetting agent in addition to the hydrazide compound of the present invention within a range that does not hinder the object of the present invention.
Examples of the thermosetting agent include organic acid hydrazides, imidazole derivatives, amine compounds, polyhydric phenol compounds, and acid anhydrides.
The sealant for a liquid crystal display element of the present invention contains a curable resin.
The curable resin preferably contains an epoxy compound.
Examples of the epoxy compound include: bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol E type epoxy resin, bisphenol S type epoxy resin, 2' -diallyl bisphenol A type epoxy resin, hydrogenated bisphenol type epoxy resin, propylene oxide addition bisphenol A type epoxy resin, resorcinol type epoxy resin, biphenyl type epoxy resin, thioether type epoxy resin, diphenyl ether type epoxy resin, dicyclopentadiene type epoxy resin, naphthalene type epoxy resin, phenol novolac type epoxy resin, o-cresol novolac type epoxy resin, dicyclopentadiene novolac type epoxy resin, biphenyl novolac type epoxy resin, naphthol novolac type epoxy resin, glycidol type epoxy resin, alkyl polyol type epoxy resin, rubber modified type epoxy resin, glycidyl ester compound, and the like.
Examples of commercial products of the bisphenol a type epoxy resin include jER828EL, jER1004 (both manufactured by mitsubishi chemical company), EPICLON850 (manufactured by DIC corporation), and the like.
Examples of commercial products of the bisphenol F type epoxy resin include jER806 and jER4004 (both manufactured by Mitsubishi chemical corporation), EPICLON EXA-830CRP (manufactured by DIC corporation), and the like.
Examples of commercial products of the bisphenol E type epoxy resins include EPOMIK R710,710 (manufactured by Sanjing chemical Co., ltd.).
As a commercial product of the bisphenol S-type epoxy resin, EPICLON EXA-1514 (DIC Co.) and the like are mentioned, for example.
Examples of the commercial products of the 2,2' -diallyl bisphenol A type epoxy resin include RE-810NM (manufactured by Japanese chemical Co., ltd.).
As a commercially available product of the hydrogenated bisphenol type epoxy resin, EPICLON EXA-7015 (DIC Co.) and the like are mentioned, for example.
Examples of commercial products of the propylene oxide addition to bisphenol A type epoxy resins include EP-4000S (manufactured by ADEKA).
Examples of commercial products of the resorcinol-type epoxy resin include EX-201 (Nagase ChemteX Corporation).
Examples of commercial products of the biphenyl type epoxy resins include jER YX-4000H (manufactured by mitsubishi chemical company).
Examples of commercial products of the above-mentioned thioether type epoxy resins include YSLV-50TE (NIPPON STEEL CHEMICAL, manufactured by Material Co., ltd.).
Examples of commercial products of the diphenyl ether type epoxy resin include YSLV-80DE (NIPPON STEEL CHEMICAL & Material Co.) and the like.
Examples of commercial products of the dicyclopentadiene type epoxy resins include EP-4088S (manufactured by ADEKA).
Examples of commercial products of the naphthalene type epoxy resins include EPICLON HP-4032 and EPICLON EXA-4700 (all manufactured by DIC Co., ltd.).
As a commercially available product of the phenol novolac type epoxy resin, EPICLON N-770 (DIC Co.) and the like are mentioned, for example.
As a commercially available product of the o-cresol novolac type epoxy resin, EPICLON N-670-EXP-S (DIC Co.) and the like are mentioned, for example.
As a commercially available product of the dicyclopentadiene phenol type epoxy resin, EPICLON HP-7200 (DIC Co.) and the like are mentioned, for example.
Examples of the commercial products of the biphenyl phenol type epoxy resins include NC-3000P (manufactured by Japanese chemical Co., ltd.).
Examples of the commercial products of the naphthol novolac type epoxy resins include ESN-165S (NIPPON STEEL CHEMICAL, manufactured by Material Co., ltd.).
Examples of commercial products of the glycidylamine-type epoxy resins include jER630 (manufactured by Mitsubishi chemical corporation), EPICLON430 (manufactured by DIC corporation), TETRAD-X (manufactured by Mitsubishi gas chemical corporation), and the like.
Examples of commercial products of the alkyl polyol type epoxy resin include ZX-1542 (NIPPON STEEL CHEMICAL & Material Co., ltd.), EPICLON (DIC Co., ltd.), epoligo 80MFA (Co., ltd.), denacol EX-611 (Nagase ChemteX Corporation Co., ltd.), and the like.
Examples of the commercial products of the rubber-modified epoxy resin include YR-450, YR-207 (both of which are manufactured by NIPPON STEEL CHEMICAL & Material Co., ltd.), and EpoleadPB (manufactured by DAICEL Co., ltd.).
Examples of the commercial products of the above glycidyl ester compounds include Denacol EX-147 (Nagase ChemteX Corporation).
Examples of other commercially available products of the epoxy compounds include YDC-1312, YSLV-80XY, YSLV-90CR (all of which are manufactured by NIPPON STEEL CHEMICAL & Material Co., ltd.), XAC4151 (manufactured by Asahi chemical Co., ltd.), jER1031, jER1032 (all of which are manufactured by Mitsubishi chemical Co., ltd.), EXA-7120 (manufactured by DIC Co., ltd.), TEPIC (manufactured by Nissan chemical Co., ltd.), and the like.
As the above epoxy compound, a partially (meth) acrylic modified epoxy resin can also be suitably used.
In the present specification, the term "partially (meth) acrylic-modified epoxy resin" means: a compound having 1 or more epoxy groups and a (meth) acryloyl group in 1 molecule, which is obtained by reacting an epoxy group of a part of an epoxy compound having 2 or more epoxy groups with (meth) acrylic acid.
In the present specification, the term "(meth) acrylic" refers to acrylic acid or methacrylic acid, and the term "(meth) acryl" refers to acryl or methacryl.
Examples of commercial products of the part of the (meth) acrylic-modified epoxy resin include UVACURE1561 and KRM8287 (both manufactured by DAICEL ALLNEX).
The curable resin may contain a (meth) acrylic compound.
Examples of the (meth) acrylic compound include: (meth) acrylate compounds, epoxy (meth) acrylates, urethane (meth) acrylates, and the like. Among them, epoxy (meth) acrylate is preferable. In addition, from the viewpoint of reactivity, the (meth) acrylic compound is preferably a compound having 2 or more (meth) acryloyl groups in 1 molecule.
In the present specification, the "(meth) acrylic compound" refers to a compound having a (meth) acryloyl group. The "(meth) acrylate" refers to an acrylate or a methacrylate, and the "epoxy (meth) acrylate" refers to a compound obtained by reacting all epoxy groups in an epoxy compound with (meth) acrylic acid.
Examples of the monofunctional compound in the (meth) acrylate compound include: methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, isononyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, isomyristyl (meth) acrylate, stearyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentenyl (meth) acrylate, benzyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2-butoxyethyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, methoxyethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, dicyclopentenyl (meth) acrylate, and process for the preparation of the same, tetrahydrofurfuryl (meth) acrylate, ethylcarbitol (meth) acrylate, 2-trifluoroethyl (meth) acrylate, 2, 3-tetrafluoropropyl (meth) acrylate, 1H, 5H-octafluoropentyl (meth) acrylate, imide (meth) acrylate, dimethylaminoethyl (meth) acrylate, and diethylaminoethyl (meth) acrylate, 2- (meth) acryloyloxyethyl succinate, 2- (meth) acryloyloxyethyl hexahydrophthalate, 2- (meth) acryloyloxyethyl 2-hydroxypropyl phthalate, 2- (meth) acryloyloxyethyl phosphate, glycidyl (meth) acrylate, and the like.
Examples of the 2-functional compound in the (meth) acrylate compound include: 1, 3-butanediol di (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, 1, 9-nonanediol di (meth) acrylate, 1, 10-decanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, 2-n-butyl-2-ethyl-1, 3-propanediol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate neopentyl glycol di (meth) acrylate, ethylene oxide addition bisphenol A di (meth) acrylate, propylene oxide addition bisphenol A di (meth) acrylate, ethylene oxide addition bisphenol F di (meth) acrylate, dimethylol dicyclopentadiene di (meth) acrylate, ethylene oxide modified isocyanuric acid di (meth) acrylate, 2-hydroxy-3- (meth) acryloxypropyl (meth) acrylate, carbonate diol di (meth) acrylate, polyether diol di (meth) acrylate, polyester diol di (meth) acrylate, polycaprolactone diol di (meth) acrylate, polybutadiene diol di (meth) acrylate, and the like.
Examples of the compound having 3 or more functions among the (meth) acrylate compounds include: trimethylolpropane tri (meth) acrylate, ethylene oxide-added trimethylolpropane tri (meth) acrylate, propylene oxide-added trimethylolpropane tri (meth) acrylate, caprolactone-modified trimethylolpropane tri (meth) acrylate, ethylene oxide-added isocyanuric acid tri (meth) acrylate, glycerol tri (meth) acrylate, propylene oxide-added glycerol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, tri (meth) acryloxyethyl phosphate, bis (trimethylolpropane) tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and the like.
Examples of the epoxy (meth) acrylate include those obtained by reacting an epoxy compound with (meth) acrylic acid in the presence of a basic catalyst according to a conventional method.
As the epoxy compound serving as a raw material for synthesizing the epoxy (meth) acrylate, the same epoxy compounds as those mentioned above as the curable resin contained in the sealing agent for a liquid crystal display element of the present invention can be used.
Examples of the commercial products of the epoxy (meth) acrylates include epoxy (meth) acrylates manufactured by DAICEL ALLNEX, epoxy (meth) acrylates manufactured by Xinzhou chemical industry, epoxy (meth) acrylates manufactured by co-mingling chemical industry, and epoxy (meth) acrylates manufactured by Nagase ChemteX Corporation.
Examples of the epoxy (meth) acrylate manufactured by DAICEL ALLNEX include EBECRYL860、EBECRYL3200、EBECRYL3201、EBECRYL3412、EBECRYL3600、EBECRYL3700、EBECRYL3701、EBECRYL3702、EBECRYL3703、EBECRYL3708、EBECRYL3800、EBECRYL6040、EBECRYL RDX63182.
Examples of the epoxy (meth) acrylate include EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, and EMA-1020.
Examples of the epoxy (meth) acrylate manufactured by the co-company chemical company include EPOXY ESTER M-600A、EPOXY ESTER 40EM、EPOXY ESTER 70PA、EPOXY ESTER 200PA、EPOXY ESTER 80MFA、EPOXY ESTER 3002M、EPOXY ESTER 3002A、EPOXY ESTER 1600A、EPOXY ESTER 3000M、EPOXY ESTER 3000A、EPOXY ESTER 200EA、EPOXY ESTER 400EA.
Examples of the Nagase ChemteX Corporation epoxy (meth) acrylate include DENACOL ACRYLATE DA-141, DENACOL ACRYLATE DA-314, DENACOL ACRYLATE DA-911, and the like.
The urethane (meth) acrylate can be obtained, for example, by reacting a (meth) acrylic derivative having a hydroxyl group with an isocyanate compound in the presence of a catalytic amount of a tin compound.
Examples of the isocyanate compound used as a raw material of the urethane (meth) acrylate include isophorone diisocyanate, 2, 4-toluene diisocyanate, 2, 6-toluene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, diphenylmethane-4, 4' -diisocyanate (MDI), hydrogenated MDI, polymeric MDI, 1, 5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate, xylylene Diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, triphenyl phosphorothioate, tetramethylxylylene diisocyanate, and 1,6, 11-undecane triisocyanate.
As the isocyanate compound to be a raw material of the urethane (meth) acrylate, a chain-extended isocyanate compound obtained by reacting a polyol with an excessive amount of the isocyanate compound can also be used.
Examples of the polyhydric alcohol include ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate diol, polyether diol, polyester diol, and polycaprolactone diol.
Examples of the (meth) acrylic derivative having a hydroxyl group include: hydroxyalkyl mono (meth) acrylates, mono (meth) acrylates of diols, mono (meth) acrylates or di (meth) acrylates of triols, epoxy (meth) acrylates, and the like.
Examples of the hydroxyalkyl mono (meth) acrylate include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate.
Examples of the dihydric alcohol include ethylene glycol, propylene glycol, 1, 3-propanediol, 1, 3-butanediol, 1, 4-butanediol, and polyethylene glycol.
Examples of the triol include trimethylolethane, trimethylolpropane, and glycerin.
Examples of the epoxy (meth) acrylate include bisphenol a type epoxy acrylate.
Examples of commercial products of the urethane (meth) acrylate include urethane (meth) acrylate produced by east asia synthesis company, urethane (meth) acrylate produced by DAICEL ALLNEX, urethane (meth) acrylate produced by the root industry company, urethane (meth) acrylate produced by the new yo chemical industry company, and urethane (meth) acrylate produced by the co-Rong chemical industry company.
Examples of the urethane (meth) acrylate produced by the east Asia synthetic company include M-1100, M-1200, M-1210, and M-1600.
Examples of urethane (meth) acrylate manufactured by DAICEL ALLNEX include EBECRYL210、EBECRYL220、EBECRYL230、EBECRYL270、EBECRYL1290、EBECRYL2220、EBECRYL4827、EBECRYL4842、EBECRYL4858、EBECRYL5129、EBECRYL6700、EBECRYL8402、EBECRYL8803、EBECRYL8804、EBECRYL8807、EBECRYL9260.
Examples of the urethane (meth) acrylate manufactured by the above-mentioned industrial company include Artresin UN-330、Artresin SH-500B、Artresin UN-1200TPK、Artresin UN-1255、Artresin UN-3320HB、Artresin UN-7100、Artresin UN-9000A、Artresin UN-9000H.
Examples of the urethane (meth) acrylate manufactured by the chemical industry company in the new country include U-2HA、U-2PHA、U-3HA、U-4HA、U-6H、U-6HA、U-6LPA、U-10H、U-15HA、U-108、U-108A、U-122A、U-122P、U-324A、U-340A、U-340P、U-1084A、U-2061BA、UA-340P、UA-4000、UA-4100、UA-4200、UA-4400、UA-5201P、UA-7100、UA-7200、UA-W2A.
As urethane (meth) acrylate produced by the company of Cooperation, AH-600, AI-600, AT-600, UA-101I, UA-101T, UA-306H, UA-306I, UA-306T and the like are mentioned, for example.
When the (meth) acrylic compound is contained in addition to the epoxy compound or when the partially (meth) acrylic-modified epoxy compound is contained in the curable resin, the ratio of the (meth) acryloyl group in the total of the epoxy groups and the (meth) acryloyl groups in the curable resin is preferably 30 mol% or more and 95 mol% or less. When the ratio of the (meth) acryloyl groups is in this range, the occurrence of liquid crystal contamination is suppressed, and the resulting sealant for a liquid crystal display element has more excellent adhesion.
The curable resin preferably has hydrogen bonding units such as-OH groups, -NH-groups, -NH 2 groups, and the like, from the viewpoint of further suppressing contamination of the liquid crystal.
The sealant for a liquid crystal display element of the present invention preferably further contains a photo radical polymerization initiator.
Examples of the photo-radical polymerization initiator include benzophenone compounds, acetophenone compounds, acylphosphine oxide compounds, titanocene compounds, oxime ester compounds, benzoin ether compounds, thioxanthone compounds, and the like.
Specific examples of the photo-radical polymerization initiator include 1-hydroxycyclohexylphenyl ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -1-butanone, 2- (dimethylamino) -2- ((4-methylphenyl) methyl) -1- (4- (4-morpholinyl) phenyl) -1-butanone, 2-dimethoxy-1, 2-diphenylethane-1-one, bis (2, 4, 6-trimethylbenzoyl) phenylphosphine oxide, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropane-1-one, 1- (4- (2-hydroxyethoxy) -phenyl) -2-hydroxy-2-methyl-1-propan-1-one, 1- (4- (phenylthio) phenyl) -1, 2-octanedione 2- (O-benzoyl oxime), and 2,4, 6-trimethylbenzoyl diphenylphosphine oxide.
The photo radical polymerization initiator may be used alone or in combination of 2 or more.
The content of the photo radical polymerization initiator is preferably 0.5 parts by weight, and the upper limit is preferably 10 parts by weight, based on 100 parts by weight of the curable resin. When the content of the photo radical polymerization initiator is within this range, the resulting sealant for a liquid crystal display element can suppress liquid crystal contamination, and is further excellent in storage stability and photocurability. The more preferable lower limit of the content of the above-mentioned photo radical polymerization initiator is 1 part by weight, and the more preferable upper limit is 7 parts by weight.
The sealant for a liquid crystal display element of the present invention may contain a thermal radical polymerization initiator.
Examples of the thermal radical polymerization initiator include polymerization initiators composed of azo compounds, organic peroxides, and the like. Among them, an initiator composed of an azo compound (hereinafter, also referred to as "azo initiator") is preferable from the viewpoint of suppressing liquid crystal contamination, and an initiator composed of a polymer azo compound (hereinafter, also referred to as "polymer azo initiator") is more preferable.
The thermal radical polymerization initiator may be used alone or in combination of 2 or more.
In the present specification, the term "polymer azo compound" refers to a compound having an azo group and having a number average molecular weight of 300 or more, which generates radicals capable of curing a (meth) acryloyl group by heat.
The number average molecular weight of the polymer azo compound is preferably 1000 at the lower limit and 30 tens of thousands at the upper limit. When the number average molecular weight of the polymer azo compound is in this range, adverse effects on the liquid crystal can be prevented and the polymer azo compound can be easily mixed with the curable resin. The number average molecular weight of the polymer azo compound is more preferably limited to 5000, more preferably to 10 ten thousand, still more preferably to 1 ten thousand, and still more preferably to 9 ten thousand.
In the present specification, the number average molecular weight is a value obtained by measuring the number average molecular weight by Gel Permeation Chromatography (GPC) using tetrahydrofuran as a solvent and converting the number average molecular weight into polystyrene. Examples of the column used for measuring the number average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa electric company).
Examples of the polymer azo compound include: a polymer azo compound having a structure in which a plurality of units such as polyalkylene oxide and polydimethylsiloxane are bonded via azo groups.
The polymer azo compound having a structure in which a plurality of units such as polyalkylene oxide are bonded via azo groups is preferably a polymer azo compound having a polyethylene oxide structure.
Specific examples of the polymer azo compound include a polycondensate of 4,4 '-azobis (4-cyanovaleric acid) and polyalkylene glycol, and a polycondensate of 4,4' -azobis (4-cyanovaleric acid) and polydimethylsiloxane having a terminal amino group.
Examples of the commercially available products of the polymeric azo initiator include VPE-0201, VPE-0401, VPE-0601, VPS-0501, and VPS-1001 (both manufactured by Fuji film and Wako pure chemical industries, ltd.).
Examples of azo initiators other than polymers include V-65 and V-501 (both of Fuji photo-chemical Co., ltd.).
Examples of the organic peroxide include ketone peroxide, ketal peroxide, hydrogen peroxide, dialkyl peroxide, peroxyester, diacyl peroxide, and peroxydicarbonate.
The content of the thermal radical polymerization initiator is preferably 0.1 part by weight, and the upper limit is preferably 10 parts by weight, based on 100 parts by weight of the curable resin. When the content of the thermal radical polymerization initiator is within this range, the resulting sealant for a liquid crystal display element is more excellent in storage stability and thermosetting property while suppressing contamination of liquid crystal. The more preferable lower limit of the content of the thermal radical polymerization initiator is 0.3 parts by weight, and the more preferable upper limit is 5 parts by weight.
The sealant for a liquid crystal display element of the present invention may contain a filler for the purpose of increasing viscosity, improving adhesiveness due to a stress dispersion effect, improving linear expansion coefficient, improving moisture resistance of a cured product, and the like.
As the filler, an inorganic filler and an organic filler can be used.
Examples of the inorganic filler include silica, talc, glass beads, asbestos, gypsum, diatomaceous earth, smectite, bentonite, montmorillonite, sericite, activated clay, alumina, zinc oxide, iron oxide, magnesium oxide, tin oxide, titanium oxide, calcium carbonate, magnesium hydroxide, aluminum nitride, silicon nitride, barium sulfate, and calcium silicate.
Examples of the organic filler include polyester fine particles, polyurethane fine particles, vinyl polymer fine particles, and acrylic polymer fine particles.
The above fillers may be used alone or in combination of 2 or more.
The preferable lower limit of the content of the filler in 100 parts by weight of the sealant for a liquid crystal display element of the present invention is 10 parts by weight, and the preferable upper limit is 70 parts by weight. When the content of the filler is in this range, the effect of improving the adhesion and the like is more excellent without deteriorating the coating property and the like. The lower limit of the content of the filler is more preferably 20 parts by weight, and the upper limit is more preferably 60 parts by weight.
The sealant for a liquid crystal display element of the present invention may contain a silane coupling agent. The silane coupling agent mainly has a role as an adhesion promoter for favorably adhering a sealing agent for a liquid crystal display element to a substrate or the like.
As the silane coupling agent, for example, 3-aminopropyl trimethoxysilane, 3-mercaptopropyl trimethoxysilane, 3-glycidoxypropyl trimethoxysilane, 3-isocyanatopropyl trimethoxysilane, and the like can be suitably used. These silane coupling agents have excellent effect of improving adhesion to substrates and the like, and can inhibit the outflow of the curable resin into the liquid crystal by chemical bonding with the curable resin.
The silane coupling agent may be used alone or in combination of 2 or more.
The preferable lower limit of the content of the silane coupling agent in 100 parts by weight of the sealant for a liquid crystal display element of the present invention is 0.1 part by weight, and the preferable upper limit is 10 parts by weight. When the content of the silane coupling agent is within this range, the occurrence of liquid crystal contamination is suppressed, and the effect of improving the adhesion is more excellent. The more preferable lower limit of the content of the above silane coupling agent is 0.3 parts by weight, and the more preferable upper limit is 5 parts by weight.
The sealant for a liquid crystal display element of the present invention may contain a light shielding agent. By containing the above-described light-shielding agent, the sealant for a liquid crystal display element of the present invention can be suitably used as a light-shielding sealant.
Examples of the light-shielding agent include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, and resin-coated carbon black. Among them, titanium black is preferable.
The titanium black is a substance having a higher transmittance for light in the vicinity of the ultraviolet region, particularly at a wavelength of 370nm to 450nm, than an average transmittance for light at a wavelength of 300nm to 800 nm. That is, the titanium black is an opacifier having the following properties: the sealant for a liquid crystal display element of the present invention is provided with light shielding properties by sufficiently shielding light having a wavelength in the visible light range, while transmitting light having a wavelength in the vicinity of the ultraviolet range. Therefore, as the photo radical polymerization initiator, an initiator capable of initiating a reaction by using light having a wavelength at which the transmittance of the titanium black becomes high is used, whereby the photocurability of the sealant for a liquid crystal display element of the present invention can be further increased. On the other hand, the light-shielding agent contained in the sealant for a liquid crystal display element of the present invention is preferably a material having high insulation properties, and titanium black is also suitable as the light-shielding agent having high insulation properties.
The optical density (OD value) of the titanium black per 1 μm is preferably 3 or more, more preferably 4 or more. The higher the light-shielding property of the titanium black, the better, and the upper limit of the OD value of the titanium black is preferably not particularly limited, but is usually 5 or less.
The titanium black exhibits a sufficient effect even without surface treatment, but it is also possible to use a surface-treated titanium black such as a titanium black surface-treated with an organic component such as a coupling agent or a titanium black surface-coated with an inorganic component such as silicon oxide, titanium oxide, germanium oxide, aluminum oxide, zirconium oxide, magnesium oxide. Among them, titanium black treated with an organic component is preferable from the viewpoint of further improving the insulation property.
Further, since a liquid crystal display element produced using the sealant for a liquid crystal display element of the present invention in which the titanium black is blended as a light shielding agent has a sufficient light shielding property, it is possible to realize: a liquid crystal display device having high contrast without light leakage and excellent image display quality.
Examples of the commercial products of the titanium black include titanium black manufactured by Mitsubishi composite materials, titanium black manufactured by red scion chemical corporation, and the like.
Examples of the titanium black manufactured by Mitsubishi composite Co., ltd include 12S, 13M-C, 13R-N, and 14M-C.
Examples of the titanium black manufactured by red-tab chemical industry include Tilack D.
The specific surface area of the titanium black is preferably limited to 13m 2/g at a lower limit, 30m 2/g at an upper limit, 15m 2/g at a lower limit, and 25m 2/g at an upper limit.
The preferable lower limit of the volume resistivity of the titanium black is 0.5 Ω·cm, the preferable upper limit is 3 Ω·cm, the more preferable lower limit is 1 Ω·cm, and the more preferable upper limit is 2.5 Ω·cm.
The primary particle diameter of the light-shielding agent is not particularly limited as long as it is not more than the distance between substrates of the liquid crystal display element, and is preferably limited to 1nm at a lower limit and 5000nm at an upper limit. By setting the primary particle diameter of the light-shielding agent to this range, the light-shielding property can be further improved without deteriorating the coating property and the like of the obtained sealing agent for a liquid crystal display element. The primary particle diameter of the light-shielding agent is more preferably 5nm in lower limit, more preferably 200nm in upper limit, still more preferably 10nm in lower limit, and still more preferably 100nm in upper limit.
The primary particle size of the light-shielding agent may be measured by dispersing the light-shielding agent in a solvent (water, organic solvent, etc.) using NICOMP 380ZLS (PARTICLE SIZING SYSTEMS).
The lower limit of the content of the light shielding agent in 100 parts by weight of the sealant for a liquid crystal display element of the present invention is preferably 5 parts by weight, and the upper limit is preferably 80 parts by weight. By setting the content of the light-shielding agent to this range, more excellent light-shielding properties can be exhibited without significantly reducing the adhesiveness, the strength after curing, and the paintability of the obtained sealant for a liquid crystal display element. The content of the light-shielding agent is more preferably 10 parts by weight, still more preferably 70 parts by weight, still more preferably 30 parts by weight, and still more preferably 60 parts by weight.
The sealant for a liquid crystal display element of the present invention may further contain additives such as a stress relaxation agent, a reactive diluent, a thixotropic agent, a spacer, a curing accelerator, an antifoaming agent, a leveling agent, and a polymerization inhibitor, as necessary.
Examples of the method for producing the sealant for a liquid crystal display element of the present invention include a method in which a curable resin, a thermosetting agent, a thermal radical polymerization initiator added as needed, and the like are mixed using a mixer.
Examples of the mixer include a homogenizing and dispersing machine, a homogenizing and mixing machine, a universal mixer, a planetary mixer, a kneader, and a three-roll machine.
By incorporating conductive fine particles into the sealing agent for a liquid crystal display element of the present invention, a vertically conductive material can be produced. Such a vertically conductive material containing the sealing agent for a liquid crystal display element and conductive fine particles of the present invention is also one of the present invention.
As the conductive fine particles, for example, metal spheres, fine particles having a conductive metal layer formed on the surface of a resin fine particle, or the like can be used. Among them, the fine particles having the conductive metal layer formed on the surface of the fine resin particles are suitable because the fine resin particles have excellent elasticity and can be electrically connected without damaging the transparent substrate or the like.
The liquid crystal display element using the sealant for a liquid crystal display element of the present invention or the vertically conductive material of the present invention is also one of the present invention.
The liquid crystal display element of the present invention is preferably a narrow frame design. Specifically, the width of the frame portion around the liquid crystal display portion is preferably 2mm or less.
The width of the sealant for a liquid crystal display element of the present invention applied in the production of the liquid crystal display element of the present invention is preferably 1mm or less.
The sealant for a liquid crystal display element of the present invention can be suitably used for manufacturing a liquid crystal display element by a liquid crystal dropping process.
Examples of the method for manufacturing the liquid crystal display element of the present invention by the liquid crystal dropping method include the following methods.
First, a step of forming a frame-like seal pattern on a substrate by screen printing, dispenser coating, or the like, with the sealant for a liquid crystal display element of the present invention; next, a step of applying droplets of liquid crystal to the entire inner surface of the frame of the seal pattern in an uncured state of the sealant for a liquid crystal display element of the present invention, and immediately superposing the other substrate is performed; then, a step of heating the sealing agent to cure the sealing agent is performed, whereby a liquid crystal display element can be obtained by a method of performing the above step. Further, before the step of heating the sealant to cure it, a step of pre-curing the sealant by irradiating the seal pattern portion with light such as ultraviolet rays may be performed.
Effects of the invention
According to the present invention, a sealant for a liquid crystal display element excellent in storage stability, adhesiveness, and low liquid crystal contamination can be provided. Further, according to the present invention, it is possible to provide a vertically conductive material and a liquid crystal display element using the sealant for a liquid crystal display element.
Detailed Description
Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited to these examples.
(Synthesis of Compound A)
In a 3-neck flask equipped with a reflux condenser, a thermometer, and a stirrer, 208.3g (2.0 mol) of styrene (manufactured by Fuji photo-pure chemical Co., ltd.) and 172.1g (2.0 mol) of methyl acrylate (manufactured by Tokyo chemical industry Co., ltd.) were dissolved in 300mL of tetrahydrofuran. To the resulting solution, 16.4g (0.1 mol) of azobisisobutyronitrile was added as a polymerization initiator, and the mixture was stirred at 80℃for 1 hour to react with nitrogen substitution. The obtained reaction product was concentrated and reprecipitated in an ethanol solution to obtain an intermediate polymer compound.
In a 3-neck flask equipped with a reflux condenser, a thermometer, and a stirrer, 113g (2.3 moles) of the obtained intermediate polymer compound and hydrazine hydrate were dissolved in 200mL of tetrahydrofuran, and the reaction was performed under reflux for 3 hours. After the completion of the reaction, the solid component was separated by concentrating the mixture, whereby compound a was obtained.
From 1 H-NMR, MS, and FT-IR, it was confirmed that the obtained compound A was a compound having the structure represented by the above formula (1-1) (Ar is phenyl), the structure represented by the above formula (1-2) (R 1 is hydrogen atom), and the structure represented by the above formula (2) (R 2 is hydrogen atom, R 3 is-C (=O) OCH 3 group). The compound A thus obtained had a structure represented by the above formula (1-1) at 50 mol%. Further, the weight average molecular weight of the obtained compound a was 15000, and the softening point was 130 ℃.
(Synthesis of Compound B)
Compound B was obtained as the hydrazide compound of the present invention in the same manner as the "(synthesis of compound a)" described above except that the stirring time was changed to 4 hours when stirring was performed at 80 ℃ while nitrogen substitution was performed.
From 1 H-NMR, MS, and FT-IR, it was confirmed that the obtained compound B was a compound having the structure represented by the above formula (1-1) (Ar is phenyl), the structure represented by the above formula (1-2) (R 1 is a hydrogen atom), and the structure represented by the above formula (2) (R 2 is a hydrogen atom, and R 3 is a-C (=O) OCH 3 group). The compound B thus obtained had a structure represented by the above formula (1-1) at 50 mol%. The weight average molecular weight of the compound B obtained was 7 ten thousand, and the softening point was 147 ℃.
(Synthesis of Compound C)
Compound C was obtained as the hydrazide compound of the present invention in the same manner as the "(synthesis of compound a)" described above except that the stirring time was changed to 0.5 hours when stirring was performed at 80 ℃ while nitrogen substitution was performed.
From 1 H-NMR, MS, and FT-IR, it was confirmed that the compound C obtained was a compound having the structure represented by the above formula (1-1) (Ar is phenyl), the structure represented by the above formula (1-2) (R 1 is a hydrogen atom), and the structure represented by the above formula (2) (R 2 is a hydrogen atom, and R 3 is a-C (=O) OCH 3 group). The compound C thus obtained had a structure represented by the above formula (1-1) at 50 mol%. Further, the weight average molecular weight of the obtained compound C was 3000, and the softening point was 92 ℃.
(Synthesis of Compound D)
Compound D was obtained as a hydrazide compound of the present invention in the same manner as the "(synthesis of compound a)" described above except that the amount of styrene was changed to 416.6g (4.0 mol), the amount of methyl acrylate was changed to 86.0g (1.0 mol), and the amount of hydrazine hydrate was changed to 60g (1.2 mol).
From 1 H-NMR, MS, and FT-IR, it was confirmed that the obtained compound D was a compound having the structure represented by the above formula (1-1) (Ar is phenyl), the structure represented by the above formula (1-2) (R 1 is a hydrogen atom), and the structure represented by the above formula (2) (R 2 is a hydrogen atom, and R 3 is a-C (=O) OCH 3 group). The compound D thus obtained had a structure represented by the above formula (1-1) at 80 mol%. The weight average molecular weight of the compound D obtained was 25000 and the softening point was 156 ℃.
(Synthesis of Compound E)
The procedure was similar to the above "(synthesis of compound a)" except that the amount of styrene was changed to 494.7g (4.75 mol), the amount of methyl acrylate was changed to 21.5g (0.25 mol), and the amount of hydrazine hydrate was changed to 20g (0.4 mol), to obtain compound E as a hydrazide compound of the present invention.
From 1 H-NMR, MS, and FT-IR, it was confirmed that the obtained compound E was a compound having the structure represented by the above formula (1-1) (Ar is phenyl), the structure represented by the above formula (1-2) (R 1 is a hydrogen atom), and the structure represented by the above formula (2) (R 2 is a hydrogen atom, and R 3 is a-C (=O) OCH 3 group). The compound E thus obtained had a structure represented by the above formula (1-1) at 95 mol%. Further, the weight average molecular weight of the obtained compound E was 24000, and the softening point was 200 ℃.
(Synthesis of Compound F)
The procedure was similar to the above "(synthesis of compound a)" except that the amount of styrene was changed to 26.0g (0.25 mol), the amount of methyl acrylate was changed to 408.7g (4.75 mol), and the amount of hydrazine hydrate was changed to 275g (5.5 mol), to obtain compound F as a hydrazide compound of the present invention.
From 1 H-NMR, MS, and FT-IR, it was confirmed that the obtained compound F was a compound having the structure represented by the above formula (1-1) (Ar is phenyl), the structure represented by the above formula (1-2) (R 1 is a hydrogen atom), and the structure represented by the above formula (2) (R 2 is a hydrogen atom, and R 3 is a-C (=O) OCH 3 group). The compound F thus obtained had a structure represented by the above formula (1-1) at 5 mol%. Further, the weight average molecular weight of the obtained compound F was 16000, and the softening point was 69 ℃.
(Synthesis of Compound G)
In a 3-neck flask equipped with a reflux condenser, a thermometer, and a stirrer, 86.1g (1.0 mol) of methyl acrylate (manufactured by tokyo chemical industry Co., ltd.) and 116.1g (1.0 mol) of 2-hydroxyethyl acrylate (manufactured by tokyo chemical industry Co., ltd.) were dissolved in 150mL of tetrahydrofuran. To the resulting solution, 16.4g (0.1 mol) of azobisisobutyronitrile was added as a polymerization initiator, and the mixture was stirred at 80℃for 2 hours while nitrogen substitution was performed to react. The obtained reaction product was concentrated and reprecipitated in an ethanol solution to obtain an intermediate polymer compound.
In a 3-neck flask equipped with a reflux condenser, a thermometer, and a stirrer, 113g (2.3 moles) of the obtained intermediate polymer compound and hydrazine hydrate were dissolved in 100mL of methanol and 10mL of water, and the reaction was performed under reflux for 3 hours. After the completion of the reaction, the solid component was separated by concentrating the mixture, whereby compound G was obtained.
From 1 H-NMR, MS and FT-IR, it was confirmed that the compound G obtained was a compound represented by the following formula (5). The weight average molecular weight of the compound G obtained was 12000, and the softening point was 64 ℃.
[ Chemical 5]
In the formula (5), m and n are repeated numbers.
Examples 1 to 10 and comparative examples 1 to 3
The respective materials were mixed by using a planetary mixer (manufactured by Thinky corporation, defoamed, i.e., i.a. In japan) according to the compounding ratios shown in tables 1 and 2, and then further mixed by using a three-roll mixer, thereby preparing the respective sealing agents for liquid crystal display elements of examples 1 to 10 and comparative examples 1 to 3.
< Evaluation >
The following evaluations were performed for the sealants for liquid crystal display elements obtained in examples and comparative examples. The results are shown in tables 1 and 2.
(Storage stability)
The initial viscosity immediately after production and the viscosity after storage at 25 ℃ for 1 week after production were measured for each of the sealants for liquid crystal display elements obtained in examples and comparative examples. The storage stability was evaluated by taking (viscosity after storage)/(initial viscosity) as the thickening ratio, and taking the case where the thickening ratio is less than 1.1 as "excellent", the case where 1.1 or more and less than 1.5 as "good", the case where 1.5 or more and less than 2.0 as "delta", and the case where 2.0 or more as good as "x".
The viscosity of the sealant for a liquid crystal display element was measured using an E-type viscometer (manufactured by BROOK FIELD, inc. 'DV-III'), at 25℃and a rotation speed of 1.0 rpm.
(Adhesiveness)
The liquid crystal display element sealants obtained in examples and comparative examples were filled into dispensing syringes (manufactured by Musashi Engineering, inc., "PSY-10E"), and subjected to defoaming treatment. The defoamed sealant for a liquid crystal display element was distributed in a square manner to the inner side 30mm from the end of the glass substrate (150 mm. Times.150 mm) by using a dispenser (SHOTMASTER 300, manufactured by Musashi Engineering Co., ltd.) and the other glass substrate (110 mm. Times.110 mm) was laminated under vacuum. The sealant for a liquid crystal display element was pre-cured by irradiation with ultraviolet rays of 100mW/cm 2 for 30 seconds using a high-pressure mercury lamp, and then heated at 120℃for 1 hour to thermally cure the sealant for a liquid crystal display element, to obtain an adhesion test piece. The end of the substrate of the obtained adhesion test piece was pressed with a metal rod having a radius of 5mm at a speed of 5mm/min, and the strength (kgf) at the time of peeling off the panel was measured, thereby calculating the adhesion force (kg/cm).
The adhesion was evaluated by marking the adhesion value as 3.5kg/cm or more as "verygood", the adhesion value as 3.0kg/cm or more and less than 3.5kg/cm as "good", the adhesion value as 2.0kg/cm or more and less than 3.0kg/cm as "delta", and the adhesion value as less than 2.0kg/cm as "X".
(Low liquid Crystal contamination (NI Point))
To the sample bottle, 0.1g of each of the sealants for liquid crystal display elements obtained in examples and comparative examples and 1g of liquid crystal (4-pentyl-4-cyanobiphenyl, manufactured by tokyo chemical industry Co., ltd.) were added. The sample bottle was put into an oven at 120℃for 1 hour, allowed to stand and return to 25℃and then the liquid crystal portion was taken out and filtered through a 0.2 μm filter to prepare a liquid crystal sample for evaluation. The obtained liquid crystal sample for evaluation (10 mg) was sealed in an aluminum sample pan, and the NI point was measured using a differential scanning calorimeter (DSC-Q100, manufactured by TA instruments Co., ltd.) at a temperature rise rate of 5℃per minute. The liquid crystal cell sealing agent and the liquid crystal 10mg which was not in contact with each other were sealed in an aluminum sample pan, and the NI point was measured at a temperature rise rate of 5 ℃/min, and the results were regarded as a blank group.
The difference between the NI point measured using the liquid crystal sample for evaluation and the NI point of the blank group was "excellent", the difference between-3℃and-2℃was "good", the difference between-5℃and-3℃was "delta", and the difference between-5℃and-5℃was "X", and the low liquid crystal contamination was evaluated.
(Display Performance of liquid Crystal display element)
1 Part by weight of spacer particles having an average particle diameter of 5 μm (manufactured by water chemical industry Co., ltd., "Micropearl SI-H050") was dispersed in 100 parts by weight of each of the sealants for liquid crystal display elements obtained in examples and comparative examples, and the resultant mixture was filled into a syringe, and deaerated by a centrifugal deaerator (Awatron AW-1). Using a dispenser to apply the defoamed sealant for liquid crystal display element to the diameter of the nozzleThe coating is performed in a frame shape on one of 2 substrates with an alignment film and ITO under conditions of 42 μm in gap between nozzles, 100 to 400kPa in discharge pressure of a syringe, and a coating speed of 60 mm/sec. At this time, the discharge pressure was adjusted so that the line width of the sealing agent for a liquid crystal display element became about 1.5 mm. Next, fine droplets of liquid crystal (4-pentyl-4-cyanobiphenyl, manufactured by tokyo chemical industry co.) were applied dropwise to the entire inner surface of the frame of the liquid crystal display element sealant of the substrate coated with the liquid crystal display element sealant, and the other substrate was bonded under vacuum. Immediately after the bonding, the sealant for a liquid crystal display element was pre-cured by irradiating the sealant for a liquid crystal display element with ultraviolet light of 100mW/cm 2 for 30 seconds. Then, the mixture was heated at 120℃for 1 hour to effect primary curing, thereby producing a liquid crystal display element.
For each of the liquid crystal display element sealants obtained in examples and comparative examples, 3 liquid crystal display elements were produced, and for each of the obtained liquid crystal display elements, the disturbance of the liquid crystal alignment in the vicinity of the liquid crystal display element sealant immediately after the production of the liquid crystal display element was visually confirmed. The alignment disorder was determined by color unevenness of the display portion, and the display performance of the liquid crystal display element was evaluated by recording "very" when no display unevenness was observed at all in the peripheral portion of the liquid crystal display element, recording "o" when slight display unevenness was observed, recording "Δ" when clear, thicker display unevenness was present, and recording "x" when clear, thicker display unevenness was spread not only in the peripheral portion but also in the central portion.
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Industrial applicability
According to the present invention, a sealant for a liquid crystal display element excellent in storage stability, adhesiveness, and low liquid crystal contamination can be provided. Further, according to the present invention, it is possible to provide a vertically conductive material and a liquid crystal display element using the sealant for a liquid crystal display element.
Claims (6)
1. A sealant for a liquid crystal display element, characterized by comprising a curable resin and a thermosetting agent, wherein,
The thermal curing agent comprises a hydrazide compound,
The weight average molecular weight of the hydrazide compound is 2000 or more and 20 ten thousand or less,
The hydrazide compound has a structure represented by the following formula (1-1) and a structure represented by the following formula (1-2), wherein the proportion of the structure represented by the formula (1-1) is 5 to 95 mol%, the proportion of the structure represented by the formula (1-2) is 5 to 95 mol%,
Ar in the formula (1-1) is an aromatic ring, and R 1 in the formula (1-2) is a hydrogen atom or a methyl group.
2. The sealant for a liquid crystal display element according to claim 1, wherein the hydrazide compound further has a structure represented by the following formula (2),
In the formula (2), R 2 is a hydrogen atom OR a methyl group, R 3 is a-C (=o) OR 4 group, a-CN group, a-OR 5 group, OR a hydrogen atom, wherein R 4 is a hydrogen atom OR an alkyl group having 1 to 10 carbon atoms, and R 5 is an alkyl group having 1 to 10 carbon atoms.
3. The sealant for a liquid crystal display element according to claim 1 or 2, wherein the softening point of the hydrazide compound is 65 ℃ or higher and 200 ℃ or lower.
4. The sealant for a liquid crystal display element according to claim 1 or 2, further comprising a photo radical polymerization initiator.
5. A vertically conductive material comprising the sealant for a liquid crystal display element according to claim 1, 2,3 or 4, and conductive fine particles.
6. A liquid crystal display element comprising the sealant for a liquid crystal display element according to claim 1, 2, 3 or 4 or the vertically conductive material according to claim 5.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019-163155 | 2019-09-06 | ||
| JP2019163155 | 2019-09-06 | ||
| PCT/JP2020/031221 WO2021044842A1 (en) | 2019-09-06 | 2020-08-19 | Sealing agent for liquid crystal display elements, vertical conduction material, and liquid crystal display element |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN113874462A CN113874462A (en) | 2021-12-31 |
| CN113874462B true CN113874462B (en) | 2024-04-26 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202080037785.3A Active CN113874462B (en) | 2019-09-06 | 2020-08-19 | Sealing agent for liquid crystal display element, vertically conductive material, and liquid crystal display element |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP6821102B1 (en) |
| KR (1) | KR20220058488A (en) |
| CN (1) | CN113874462B (en) |
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| FR1212707A (en) * | 1955-08-16 | 1960-03-25 | Ciba Geigy | New polymerization products containing hydrazides or modified hydrazides of unsaturated copolymerizable acids as structural elements |
| US4544733A (en) * | 1983-11-21 | 1985-10-01 | Ajinomoto Co., Inc. | Latent curing agents for epoxy resins |
| JPS6481842A (en) * | 1987-09-24 | 1989-03-28 | Mitsubishi Yuka Badische | Stable dispersion/dissolution of water-sparingly soluble hydrazide group-containing copolymer in aqueous liquid |
| JP2004061925A (en) * | 2002-07-30 | 2004-02-26 | Nippon Kayaku Co Ltd | Liquid crystal sealing agent and liquid crystal display cell using the same |
| CN101585929A (en) * | 2009-06-25 | 2009-11-25 | 嘉兴荣泰雷帕司绝缘材料有限公司 | Hydrazide latency improving curing agent and preparation method thereof |
| KR20100028162A (en) * | 2008-09-04 | 2010-03-12 | 동우 화인켐 주식회사 | Curable resin composition and liquid crystal display device |
| JP2017223828A (en) * | 2016-06-15 | 2017-12-21 | 三井化学株式会社 | Sealant for liquid crystal dropping method, liquid crystal display panel, and method for manufacturing liquid crystal display panel |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3583326B2 (en) | 1999-11-01 | 2004-11-04 | 協立化学産業株式会社 | Sealant for dripping method of LCD panel |
| CN100487072C (en) | 2001-05-16 | 2009-05-13 | 积水化学工业株式会社 | Curing vesin composition and sealants and end-sealing materials for displays |
| JP6730133B2 (en) * | 2015-09-02 | 2020-07-29 | 積水化学工業株式会社 | Liquid crystal display element sealant, vertical conduction material and liquid crystal display element |
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2020
- 2020-08-19 CN CN202080037785.3A patent/CN113874462B/en active Active
- 2020-08-19 JP JP2020552920A patent/JP6821102B1/en active Active
- 2020-08-19 KR KR1020217028250A patent/KR20220058488A/en unknown
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1212707A (en) * | 1955-08-16 | 1960-03-25 | Ciba Geigy | New polymerization products containing hydrazides or modified hydrazides of unsaturated copolymerizable acids as structural elements |
| US4544733A (en) * | 1983-11-21 | 1985-10-01 | Ajinomoto Co., Inc. | Latent curing agents for epoxy resins |
| JPS6481842A (en) * | 1987-09-24 | 1989-03-28 | Mitsubishi Yuka Badische | Stable dispersion/dissolution of water-sparingly soluble hydrazide group-containing copolymer in aqueous liquid |
| JP2004061925A (en) * | 2002-07-30 | 2004-02-26 | Nippon Kayaku Co Ltd | Liquid crystal sealing agent and liquid crystal display cell using the same |
| KR20100028162A (en) * | 2008-09-04 | 2010-03-12 | 동우 화인켐 주식회사 | Curable resin composition and liquid crystal display device |
| CN101585929A (en) * | 2009-06-25 | 2009-11-25 | 嘉兴荣泰雷帕司绝缘材料有限公司 | Hydrazide latency improving curing agent and preparation method thereof |
| JP2017223828A (en) * | 2016-06-15 | 2017-12-21 | 三井化学株式会社 | Sealant for liquid crystal dropping method, liquid crystal display panel, and method for manufacturing liquid crystal display panel |
Also Published As
| Publication number | Publication date |
|---|---|
| JP6821102B1 (en) | 2021-01-27 |
| CN113874462A (en) | 2021-12-31 |
| JPWO2021044842A1 (en) | 2021-09-27 |
| KR20220058488A (en) | 2022-05-09 |
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