CN107250904A - Sealing material for liquid crystal display device, up and down conductive material and liquid crystal display cells - Google Patents
Sealing material for liquid crystal display device, up and down conductive material and liquid crystal display cells Download PDFInfo
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- CN107250904A CN107250904A CN201680010544.3A CN201680010544A CN107250904A CN 107250904 A CN107250904 A CN 107250904A CN 201680010544 A CN201680010544 A CN 201680010544A CN 107250904 A CN107250904 A CN 107250904A
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- JAXJOCPRSMMDFC-QCWLDUFUSA-N CC[n](c(ccc(/C(/CCC1C=CCC1)=N/OC(C)=O)c1)c1c1c2)c1ccc2C(C1SC=CC1)=O Chemical compound CC[n](c(ccc(/C(/CCC1C=CCC1)=N/OC(C)=O)c1)c1c1c2)c1ccc2C(C1SC=CC1)=O JAXJOCPRSMMDFC-QCWLDUFUSA-N 0.000 description 1
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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
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
- C08K5/3417—Five-membered rings condensed with carbocyclic rings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/378—Thiols containing heterocyclic rings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
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- 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
- 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
- C09K2003/1034—Materials or components characterised by specific properties
- C09K2003/1062—UV-curable materials
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- Chemical & Material Sciences (AREA)
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- Organic Chemistry (AREA)
- Nonlinear Science (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Mathematical Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Sealing Material Composition (AREA)
- Liquid Crystal (AREA)
Abstract
It is an object of the invention to provide photo-curable is excellent and can suppress the sealing material for liquid crystal display device of liquid crystal pollution.In addition, the present invention also aims to provide the conductive material up and down and liquid crystal display cells that are made using the sealing material for liquid crystal display device.The present invention is a kind of sealing material for liquid crystal display device, it is the sealing material for liquid crystal display device containing curable resin and optical free radical polymerization initiator, and above-mentioned optical free radical polymerization initiator contains the compound shown in compound and/or following formula (1 2) shown in following formula (1 1).In formula (1 1), X represents 2 cyclopentyl ethyls that the alkyl of carbon number 1~8 or at least one hydrogen of cyclopenta ring can be replaced by methyl or ethyl, and R represents methyl or ethyl.In formula (1 2), Y represents 2 cyclopentyl ethyls that the alkyl of carbon number 2~8 or at least one hydrogen of cyclopenta ring can be replaced by methyl or ethyl, and R represents methyl or ethyl.
Description
Technical field
The present invention relates to photo-curable is excellent and can suppress the sealing material for liquid crystal display device of liquid crystal pollution.In addition,
The invention further relates to the conductive material up and down and liquid crystal display cells being made using the sealing material for liquid crystal display device.
Background technology
In recent years, for the manufacture method of the liquid crystal display cells such as liquid crystal display, from shorten productive temp time,
Optimization using from the viewpoint of amount of liquid crystal, use patent document 1, disclosed in patent document 2 it is such, used containing solid
The property changed resin, the photo-thermal of Photoepolymerizationinitiater initiater and thermal curing agents are simultaneously referred to as the liquid crystal drop of technique of dripping with curing type sealant
Under type.
In technique of dripping, first, distributor formation rectangle is utilized on one piece of substrate in 2 pieces of electroded substrates
Seal pattern.Then, the tiny droplets of liquid crystal are added drop-wise in the sealing frame of substrate in the state of sealant is uncured, and
Overlapping another piece of substrate under vacuum, to light such as sealing irradiation ultraviolet radiations, carries out precuring.Afterwards, heat and carry out main solidification,
Make liquid crystal display cells.Now, the technique of dripping becomes the main flow of the manufacture method of liquid crystal display cells.
But, in the modern times of the various mobile device popularizations with liquid crystal panel such as mobile phone, portable game, equipment
Small-sized turn to the problem for needing most solution.As the method for the miniaturization of equipment, the narrow frame of liquid crystal display part can be enumerated,
For example carry out configuring the position of sealing under black matrix" (below, also referred to as narrow frame design).
However, because sealant configuration is in the underface of black matrix" in narrow frame design, if therefore drip work
Skill, then can block irradiated light when making sealant photocuring, light is difficult to the inside for reaching sealant, using conventional close
Solidification becomes insufficient during envelope agent.As described above, if the solidification of sealant becomes insufficient, exist uncured sealant into
Divide the problem of dissolution becomes easily to occur liquid crystal pollution into liquid crystal.
Prior art literature
Patent document
Patent document 1：Japanese Unexamined Patent Publication 2001-133794 publications
Patent document 2：International Publication No. 02/092718
The content of the invention
The invention problem to be solved
It is an object of the invention to provide photo-curable is excellent and can suppress the used for liquid crystal display element close of liquid crystal pollution
Seal agent.In addition, the present invention also aims to provide the conductive material up and down being made using the sealing material for liquid crystal display device
Material and liquid crystal display cells.
Means for solving the problems
The present invention is a kind of sealing material for liquid crystal display device, and it is triggered containing curable resin and optical free radical polymerization
The sealing material for liquid crystal display device of agent, above-mentioned optical free radical polymerization initiator contain compound shown in following formula (1-1) and/
Or the compound shown in following formula (1-2).
[changing 1]
In formula (1-1), X represents that the alkyl or at least one hydrogen of cyclopenta ring of carbon number 1~8 can be by methyl or ethyls
Substituted 2- cyclopentyl ethyls, R represents methyl or ethyl.
In formula (1-2), Y represents that the alkyl or at least one hydrogen of cyclopenta ring of carbon number 2~8 can be by methyl or ethyls
Substituted 2- cyclopentyl ethyls, R represents methyl or ethyl.
The present invention is described in detail below.
The present inventor etc. by coordinating the compound with specific structure to be used as optical free radical it has surprisingly been found that can be polymerize
Initiator is excellent and can suppress the sealing material for liquid crystal display device of liquid crystal pollution to obtain photo-curable, so that complete this
Invention.
The sealing material for liquid crystal display device of the present invention contains optical free radical polymerization initiator.
Above-mentioned optical free radical polymerization initiator contains shown in compound and/or above-mentioned formula (1-2) shown in above-mentioned formula (1-1)
Compound (below also referred to as " optical free radical polymerization initiator of the invention ").It is polymerize by the optical free radical containing the present invention
Initiator, so that the sensitivity of the sealing material for liquid crystal display device of the present invention is high and photo-curable (is particularly light shielding part
Curability) it is excellent, and liquid crystal pollution can be suppressed.
The sealing material for liquid crystal display device of the present invention preferably comprises the compound and/or following formula shown in following formula (2)
(3) compound shown in is used as optical free radical polymerization initiator of the invention, the further preferably chemical combination shown in following formula (2)
Thing.
[changing 2]
[changing 3]
Commercially available product, can enumerate such as PBG-314, PBG- in optical free radical polymerization initiator as the present invention
304 (being Changzhou electronic strong new material company system) etc..
Relative to the parts by weight of curable resin 100, the content of optical free radical polymerization initiator of the invention preferably under
It is 8 parts by weight to be limited to 0.2 parts by weight, the upper limit preferably.Content by the optical free radical polymerization initiator for making the present invention is 0.2
More than parts by weight, so that the photo-curable of the sealing material for liquid crystal display device of gained is more excellent.By the light for making the present invention
The content of radical polymerization initiator is below 8 parts by weight, so that the cementability of the sealing material for liquid crystal display device of gained
And the effect of suppression liquid crystal pollution is more excellent.The preferred lower limit of content of the optical free radical polymerization initiator of the present invention is
0.5 parts by weight, the preferred upper limit are 5 parts by weight.
In addition, in the parts by weight of sealing material for liquid crystal display device 100 of the present invention, optical free radical polymerization of the invention triggers
The preferred lower limit of the content of agent is that 0.1 parts by weight, the upper limit preferably are 5 parts by weight.By making the light of the invention described above free
The content of base polymerization initiator is more than 0.1 parts by weight, so that the photo-curable of the sealing material for liquid crystal display device of gained
It is more excellent.By making the optical free radical polymerization initiator of the present invention be below 5 parts by weight, so that the liquid crystal display cells of gained
It is more excellent with the cementability of sealant and the effect of suppression liquid crystal pollution.The content of the optical free radical polymerization initiator of the present invention
Preferred lower limit is that 0.3 parts by weight, the preferred upper limit are 3 parts by weight, and further preferred lower limit is 0.5 parts by weight, entered
The preferred upper limit of one step is 1 parts by weight.
The sealing material for liquid crystal display device of the present invention contains curable resin.
Above-mentioned curable resin preferably comprises (methyl) acrylic compounds.
As above-mentioned (methyl) acrylic compounds, the compound and (methyl) propylene for example made with hydroxyl can be enumerated
(methyl) acrylate compounds obtained by acid reaction, make (methyl) acrylic acid and epoxide react obtained by epoxy (first
Base) acrylate, make carbamic acid obtained by (methyl) acrylic acid derivative with hydroxyl and isocyanate compound reaction
Ester (methyl) acrylate etc..Wherein, preferred epoxy (methyl) acrylate.In addition, from making the high aspect of reactivity, on
State (methyl) acrylic compounds preferably has the compound of more than 2 (methyl) acryloyl groups in the molecule.
It is explained, in this manual, above-mentioned " (methyl) acrylic compounds " refer to acrylic compounds or methacrylic,
Above-mentioned " (methyl) acrylic compounds " refer to acryloyl group or methylacryloyl (hereinafter also referred to collectively as " (methyl)
Acryloyl group ") compound.In addition, above-mentioned " (methyl) acrylate " refers to acrylate or methacrylate.And then,
Above-mentioned " epoxy (methyl) acrylate " is to instigate the whole epoxy radicals and (methyl) propylene acid reaction in epoxide and obtain
The compound arrived.
As (methyl) acrylate compounds of the simple function in above-mentioned (methyl) acrylate compounds, example can be enumerated
Such as：(methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) propyl acrylate, (methyl) n-butyl acrylate, (first
Base) isobutyl acrylate, (methyl) tert-butyl acrylate, (methyl) 2-EHA, (methyl) n-octyl,
(methyl) Isooctyl acrylate monomer, the different nonyl ester of (methyl) acrylic acid, (methyl) isodecyl acrylate, (methyl) lauryl acrylate,
The different myristin of (methyl) acrylic acid, (methyl) stearyl acrylate ester, (methyl) acrylic acid 2- hydroxy methacrylates, (methyl) acrylic acid
2- hydroxy propyl esters, (methyl) acrylic acid 2- hydroxybutyls, (methyl) acrylic acid 4- hydroxybutyls, (methyl) cyclohexyl acrylate,
(methyl) isobornyl acrylate, (methyl) acrylic acid dicyclopentenyloxyethyl methacrylate, (methyl) benzyl acrylate, (methyl) acrylic acid 2- first
Epoxide ethyl ester, (methyl) acrylic acid 2- ethoxy ethyl esters, (methyl) acrylic acid 2- butoxyethyls, (methyl) acrylic acid 2- benzene oxygen
Base ethyl ester, methoxy ethyl glycol (methyl) acrylate, methoxy poly (ethylene glycol) (methyl) acrylate, phenoxy group diethylene glycol
(methyl) acrylate, phenoxy group polyethylene glycol (methyl) acrylate, (methyl) tetrahydrofurfuryl acrylate, ethyl carbitol
(methyl) acrylate, (methyl) acrylic acid 2,2,2- trifluoro ethyl esters, the tetrafluoro propyl ester of (methyl) acrylic acid 2,2,3,3-, (methyl)
Acrylic acid 1H, 1H, 5H- octafluoro pentyl ester, acid imide (methyl) acrylate, (methyl) acrylate, (first
Base) acrylic acid diethylamino ethyl ester, 2- (methyl) acryloyl-oxyethyls butanedioic acid, 2- (methyl) acryloyl-oxyethyl six
Hydrogen phthalic acid, 2- (methyl) acryloyl-oxyethyl 2- hydroxypropyl phthalates, 2- (methyl) acryloxy
Ethyl phosphonic acid ester, (methyl) glycidyl acrylate etc..
In addition, as (methyl) acrylate compounds of 2 functions in above-mentioned (methyl) acrylate compounds, can enumerate
Such as 1,3-BDO two (methyl) acrylate, BDO two (methyl) acrylate, 1,6- hexylene glycols two (methyl)
Acrylate, 1,9- nonanediols two (methyl) acrylate, 1,10- decanediols two (methyl) acrylate, (first of ethylene glycol two
Base) acrylate, diethylene glycol two (methyl) acrylate, tetraethylene glycol two (methyl) acrylate, (the first of polyethylene glycol two
Base) acrylate, 2- normal-butyls -2- ethyls -1,3-PD two (methyl) acrylate, DPG two (methyl) acrylic acid
Ester, tripropylene glycol two (methyl) acrylate, polypropylene glycol two (methyl) acrylate, neopentyl glycol two (methyl) acrylic acid
Ester, ethyleneoxide addition bisphenol-A two (methyl) acrylate, expoxy propane addition bisphenol-A two (methyl) acrylate, epoxy second
It is alkane addition Bisphenol F two (methyl) acrylate, dihydroxymethyl bicyclopentadiene two (methyl) acrylate, ethylene-oxide-modified different
Cyanurate two (methyl) acrylate, 2- hydroxyls -3- (methyl) acryloxypropyl (methyl) acrylate, carbonate diol
Two (methyl) acrylate, PTMEG two (methyl) acrylate, polyester-diol two (methyl) acrylate, polycaprolactone two
Alcohol two (methyl) acrylate, polybutadiene diol two (methyl) acrylate etc..
In addition, as (methyl) acrylate compounds in above-mentioned (methyl) acrylate compounds more than 3 functions,
It can enumerate for example：Trimethylolpropane tris (methyl) acrylate, ethyleneoxide addition trimethylolpropane tris (methyl) propylene
Acid esters, expoxy propane addition trimethylolpropane tris (methyl) acrylate, caprolactone modification trimethylolpropane tris (methyl)
Acrylate, ethyleneoxide addition isocyanuric acid three (methyl) acrylate, glycerine three (methyl) acrylate, expoxy propane add
Into glycerine three (methyl) acrylate, pentaerythrite three (methyl) acrylate, three (methyl) acryloyl-oxyethyl phosphates,
Two (trihydroxy methyl) propane four (methyl) acrylate, pentaerythrite four (methyl) acrylate, dipentaerythritol five (methyl)
Acrylate, dipentaerythritol six (methyl) acrylate etc..
As above-mentioned epoxy (methyl) acrylate, it can enumerate for example：Conventionally in the presence of base catalyst
Under make epoxide and epoxy (methyl) acrylate etc. obtained by (methyl) propylene acid reaction.
As the epoxide as the raw material for synthesizing above-mentioned epoxy (methyl) acrylate, it can enumerate for example double
Phenol A types epoxy resin, bisphenol f type epoxy resin, bisphenol-s epoxy resin, 2,2 '-diallyl bisphenol type epoxy resin, hydrogen
Change bisphenol-type epoxy resin, expoxy propane addition bisphenol A type epoxy resin, resorcinol type epoxy resin, biphenyl type epoxy tree
Fat, thioether-type epoxy resin, diphenyl ether type epoxy, dicyclopentadiene-type epoxy resin, naphthalene type epoxy resin, phenol line
Type phenol aldehyde type epoxy resin, o-cresol phenol aldehyde type epoxy resin, bicyclopentadiene novolac type epoxy resin, biphenyl line
Type phenol aldehyde type epoxy resin, naphthols novolac type epoxy resin, glycidyl amine type epoxy resin, alkyl polyols type epoxy
Resin, modified rubber type epoxy resin, epihydric alcohol ester compound etc..
As product commercially available in above-mentioned bisphenol A type epoxy resin, can enumerate such as jER828EL, jER1004 (is
Mitsubishi Chemical Ind's system), Epiclon 850CRP (DIC company systems) etc..
As product commercially available in above-mentioned bisphenol f type epoxy resin, it (is three that can enumerate such as jER806, jER4004
Water chestnut chemical company system) etc..
As product commercially available in above-mentioned bisphenol-s epoxy resin, can enumerating such as Epiclon EXA1514, (DIC is public
Department's system) etc..
As above-mentioned 2, commercially available product, can enumerate such as RE-810NM in 2 '-diallyl bisphenol type epoxy resin
(Japanese chemical drug company system) etc..
As product commercially available in above-mentioned A Hydrogenated Bisphenol A type epoxy resin, such as Epiclon EXA7015 can be enumerated
(DIC company systems) etc..
As product commercially available in above-mentioned expoxy propane addition bisphenol A type epoxy resin, such as EP-4000S can be enumerated
(ADEKA company systems) etc..
As product commercially available in above-mentioned resorcinol type epoxy resin, such as EX-201 (Nagase can be enumerated
ChemteX company systems) etc..
As product commercially available in above-mentioned biphenyl type epoxy resin, can enumerating such as jERYX-4000H, (Mitsubishi Chemical is public
Department's system) etc..
As product commercially available in above-mentioned thioether-type epoxy resin, can enumerating such as YSLV-50TE, (aurification is lived by Nippon Steel
Learn company system) etc..
As product commercially available in above-mentioned diphenyl ether type epoxy, can enumerating such as YSLV-80DE, (Nippon Steel lives
Aurification company system) etc..
As product commercially available in above-mentioned dicyclopentadiene-type epoxy resin, can enumerating such as EP-4088S, (ADEKA is public
Department's system) etc..
As product commercially available in above-mentioned naphthalene type epoxy resin, such as EpiclonHP4032, Epiclon can be enumerated
EXA-4700 (being DIC company systems) etc..
As product commercially available in above-mentioned phenol novolak type epoxy resin, such as Epiclon N-770 can be enumerated
(DIC company systems) etc..
As product commercially available in above-mentioned o-cresol phenol aldehyde type epoxy resin, such as Epiclon N- can be enumerated
670-EXP-S (DIC company systems) etc..
As product commercially available in above-mentioned bicyclopentadiene novolac type epoxy resin, such as Epiclon can be enumerated
HP7200 (DIC company systems) etc..
As product commercially available in above-mentioned biphenyl novolac type epoxy resin, such as NC-3000P (Japan can be enumerated
Chemical drug company system) etc..
As product commercially available in above-mentioned naphthols novolac type epoxy resin, such as ESN-165S (new days can be enumerated
Iron lives aurification company system) etc..
As product commercially available in above-mentioned glycidyl amine epoxy resin, can enumerating such as jER630, (Mitsubishi Chemical is public
Department's system), Epiclon 430 (DIC company systems), TETRAD-X (gas chemical company of Mitsubishi system) etc..
As product commercially available in abovementioned alkyl polyol type epoxy resin, can enumerating such as ZX-1542, (Nippon Steel lives
Aurification company system), Epiclon 726 (DIC company systems), Epolite 80MFA (chemical company of common prosperity society system), Denacol
EX-611 (Nagase ChemteX company systems) etc..
As product commercially available in above-mentioned modified rubber type epoxy resin, can enumerate such as YR-450, YR-207 (is
Aurification company system is lived by Nippon Steel), Epolide PB (Daicel company system) etc..
As product commercially available in above-mentioned epihydric alcohol ester compound, such as Denacol EX-147 can be enumerated
(Nagase ChemteX company systems) etc..
As other commercially available products in above-mentioned epoxide, it can enumerate for example：YDC-1312、YSLV-80XY、
YSLV-90CR (being that aurification company system is lived by Nippon Steel)；XAC4151 (Asahi Kasei Corporation's system)；JER1031, jER1032 are (
For Mitsubishi Chemical Ind's system)；EXA-7120 (DIC company systems)；TEPIC (Nissan Chemical company system) etc..
As product commercially available in above-mentioned epoxy (methyl) acrylate, it can enumerate for example：EBECRYL860、
EBECRYL3200、EBECRYL3201、EBECRYL3412、EBECRYL3600、EBECRYL3700、EBECRYL3701、
EBECRYL3702, EBECRYL3703, EBECRYL3800, EBECRYL6040, EBECRYLRDX63182 (are DAICEL-
ALLNEX company systems)；EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020 (are Xin Zhong villages chemistry
Industrial group's system)；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
(being chemical company of common prosperity society system)；Denacol ACRYLATE DA-141、Denacol ACRYLATE DA-314、
Denacol ACRYLATE DA-911 (being Nagase ChemteX company systems) etc..
It is used as (methyl) acrylic acid derivative made with hydroxyl and amino obtained by the reaction of above-mentioned isocyanate compound
Formic acid esters (methyl) acrylate, for example can be by making the equivalent of isocyanate compound 1 with 2 NCOs and tool
The equivalent of (methyl) acrylic acid derivative 2 of hydroxyl reacts and obtained in the presence of the tin based compound of catalytic amount.
As the isocyanate compound of the raw material as above-mentioned carbamate (methyl) acrylate, it can enumerate for example
IPDI, 2,4- toluene di-isocyanate(TDI)s, 2,6- toluene di-isocyanate(TDI)s, hexamethylene diisocyanate,
Trimethyl hexamethylene diisocyanate, diphenyl methane -4,4 '-diisocyanate (MDI), hydrogenation MDI, polymeric MDI, 1,5-
Naphthalene diisocyanate, norbornene alkyl diisocyanate, tolidine diisocyanate, XDI (XDI),
Hydrogenate XDI, lysine diisocyanate, triphenylmethane triisocyanate, three (isocyanate phenyl) thiophosphates, tetramethyl
Base XDI, 1,6,11- hendecane triisocyanates etc..
In addition, as above-mentioned carbamate (methyl) acrylate raw material isocyanate compound, for example
Ethylene glycol, propane diols, glycerine, sorbierite, trimethylolpropane, carbonate diol, PTMEG, polyester two can also be used
Isocyanates chemical combination of the polyalcohols such as alcohol, polycaprolactone glycol with chain elongation obtained by excessive isocyanate compound reaction
Thing.
Spread out as (methyl) acrylic acid with hydroxyl of the raw material as above-mentioned carbamate (methyl) acrylate
Biology, can be enumerated for example：(methyl) acrylic acid 2- hydroxy methacrylates, (methyl) acrylic acid 2- hydroxy propyl esters, (methyl) acrylic acid 2-
(methyl) hydroxyalkyl acrylates such as hydroxybutyl, (methyl) acrylic acid 4- hydroxybutyls；Ethylene glycol, propane diols, 1,3- third
List (methyl) acrylate of the dihydric alcohols such as glycol, 1,3-BDO, BDO, polyethylene glycol；Trimethylolethane, three
List (methyl) acrylate of the trihydroxylic alcohols such as hydroxymethyl-propane, glycerine or two (methyl) acrylate；Bisphenol type epoxy acrylic acid
The epoxies such as ester (methyl) acrylate etc..
As product commercially available in above-mentioned carbamate (methyl) acrylate, it can enumerate for example：M-1100、M-
1200th, M-1210, M-1600 (being East Asia Synesis Company system)；EBECRYL210、EBECRYL220、EBECRYL230、
EBECRYL270、EBECRYL1290、EBECRYL2220、EBECRYL4827、EBECRYL4842、EBECRYL4858、
EBECRYL5129、EBECRYL6700、EBECRYL8402、EBECRYL8803、EBECRYL8804、EBECRYL8807、
EBECRYL9260 (being DAICEL-ALLNEX company systems)；Art Resin UN-330、Art Resin SH-500B、Art
Resin UN-1200TPK、Art Resin UN-1255、Art Resin UN-3320HB、Art Resin UN-7100、Art
Resin UN-9000A, Art Resin UN-9000H (being Gen Shang industrial groups system)；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-
7100th, UA-/200, UA-W2A (being chemical industrial company of Xin Zhong villages system)；AH-600、AI-600、AT-600、UA-101I、
UA-101T, UA-306H, UA-306I, UA-306T (being chemical company of common prosperity society system) etc..
For the purpose of the cementability of the sealing material for liquid crystal display device obtained by raising, above-mentioned curable resin preferably enters
One step contains epoxide.As above-mentioned epoxide, it can enumerate for example：As for synthesizing above-mentioned epoxy (methyl) third
The epoxide of the raw material of olefin(e) acid ester；Partly (methyl) acrylic modified epoxy resin etc..
It is explained, in this specification, above-mentioned part (methyl) acrylic modified epoxy resin refers in 1 molecule respectively
Compound with more than 1 epoxy radicals and (methyl) acryloyl group, for example, can make one of the epoxide of more than 2
Point epoxy radicals is obtained with (methyl) propylene acid reaction.
Above-mentioned (methyl) acrylic compounds and above-mentioned epoxy are included in the sealing material for liquid crystal display device of the present invention
In the case of compound, preferably so that the ratio between (methyl) acryloyl group and epoxy radicals reach 30: 70~95: 5 mode with closing
State (methyl) acrylic compounds and above-mentioned epoxide.By making the ratio of (methyl) acryloyl group be more than 30%,
So that the effect of the suppression liquid crystal pollution of the sealing material for liquid crystal display device of gained is more excellent.By making (methyl) acryloyl
The ratio of base is less than 95%, so that the cementability of the sealing material for liquid crystal display device of gained is more excellent.
In terms of liquid crystal pollution is suppressed, above-mentioned curable resin preferably has-OH bases ,-NH- bases ,-NH2The hydrogen bonds such as base
The curable resin of property unit.
The sealing material for liquid crystal display device of the present invention can contain hot radical polymerization initiator.
As above-mentioned hot radical polymerization initiator, it can enumerate and be formed such as azo-compound, organic peroxide
Hot radical polymerization initiator.Wherein, the initiator preferably formed by polymeric azo compound (is also referred to as " high score below
Sub- azo initiator ").
It is explained, polymeric azo initiator refers in this manual：With azo group and using be thermally generated can
Make compound free radical, that number-average molecular weight is more than 300 that (methyl) acryloyl group solidifies.
The preferred lower limit of the number-average molecular weight of above-mentioned polymeric azo initiator is that the 1000, upper limit preferably is 300,000.
It is the scope by making the number-average molecular weight of above-mentioned polymeric azo initiator, so as to prevent the harmful effect to liquid crystal,
And it can be easier to be mixed into curable resin.The number-average molecular weight of above-mentioned polymeric azo initiator it is preferred under
It is 100,000 to be limited to 5000, the preferred upper limit, and further preferred lower limit is 10,000, the further preferred upper limit is 90,000.
It is explained, in this manual, above-mentioned number-average molecular weight is to be measured using gel permeation chromatography (GPC)
And the value for being converted and being tried to achieve based on polystyrene.As using GPC determine based on polystyrene convert number-average molecular weight when
Chromatographic column, can be enumerated such as Shodex LF-804 (Showa electrician company system).
As above-mentioned polymeric azo initiator, it can include for example with being bonded with multiple polycyclic oxygen via azo group
The polymeric azo initiator of the structure of the units such as alkane, dimethyl silicone polymer.
Draw as the above-mentioned polymeric azo with the structure that the units such as multiple polyalkylene oxides are bonded with via azo group
Send out agent, preferably the polymeric azo initiator with PEO structure.As such a polymeric azo initiator, it can enumerate
Such as 4, the condensation polymer of 4 '-azo double (4- cyanopentanoic acids) and PAG, 4,4 '-azo double (4- cyanopentanoic acids) and tool
Have condensation polymer of the dimethyl silicone polymer of terminal amino group etc., specifically, can enumerate such as VPE-0201, VPE-0401,
VPE-0601, VPS-0501, VPS-1001 (being and Wako Pure Chemical Industries company system) etc..
In addition, as the example for not being high molecular azo-compound, can enumerate V-65, V-501 (is and the pure medicine work of light
Industry company system) etc..
As above-mentioned organic peroxide, such as ketone peroxide, ketal peroxide, hydrogen peroxide, dialkyl group mistake can be enumerated
Oxide, peroxy esters, diacyl peroxide, peroxy dicarbonate etc..
Relative to the parts by weight of curable resin 100, the preferred lower limit of the content of above-mentioned hot radical polymerization initiator is
0.05 parts by weight, the upper limit preferably are 10 parts by weight.By making the content of above-mentioned hot radical polymerization initiator be the scope, from
And suppress the generation of the liquid crystal pollution caused by unreacted radical polymerization initiator, and make the liquid crystal display cells of gained
It is more excellent with the curability of sealant.The preferred lower limit of the content of above-mentioned hot radical polymerization initiator be 0.1 parts by weight,
The preferred upper limit is 5 parts by weight.
The sealing material for liquid crystal display device of the present invention preferably comprises thermal curing agents.
As above-mentioned thermal curing agents, such as organic acid hydrazides, imdazole derivatives, amines, polyhydric phenols system can be enumerated
Compound, acid anhydrides etc..Wherein, organic acid hydrazides is preferably used.
As above-mentioned organic acid hydrazides, such as sebacic dihydrazide, isophthalic dihydrazide, the acyl of adipic acid two can be enumerated
Hydrazine, acid dihydrazide etc..
As product commercially available in above-mentioned organic acid hydrazides, it (is great Zhuo chemical companies that can enumerate such as SDH, ADH
System), AMICURE VDH, AMICURE VDH-J, AMICURE UDH, AMICURE UDH-J (be that aginomoto microtechnic is public
Department's system) etc..
Relative to the above-mentioned parts by weight of curable resin 100, the preferred lower limit of the content of above-mentioned thermal curing agents is 1 weight
Part, the upper limit preferably are 50 parts by weight.By making the content of above-mentioned thermal curing agents be more than 1 parts by weight, so that the liquid of gained
The Thermocurable of crystal display element sealant is more excellent.By making the contents of above-mentioned thermal curing agents for below 50 parts by weight, from
And make gained sealant viscosity will not be too high and make coating more excellent.The content of above-mentioned thermal curing agents it is preferred on
It is limited to 30 parts by weight.
The sealing material for liquid crystal display device of the present invention is preferably viscous based on stress dispersion effect for viscosity, raising is improved
Connecing property, improve linear expansivity, improve the purpose such as moisture-proof of solidfied material and contain filler.
As above-mentioned filler, it can enumerate for example：Silica, talcum, bead, asbestos, gypsum, diatomite, illiteracy soap
Stone, bentonite, montmorillonite, sericite, atlapulgite, aluminum oxide, zinc oxide, iron oxide, magnesia, tin oxide, titanium oxide, carbon
The inorganic fillers such as sour calcium, magnesium carbonate, magnesium hydroxide, aluminium hydroxide, aluminium nitride, silicon nitride, barium sulfate, calcium silicates；Polyester is micro-
The organic fillers such as grain, polyurethane particulate, polyvinyl particulate, acrylic polymer particulate.These fillers can be with
It is used alone, and two or more can also be used.
In the parts by weight of sealing material for liquid crystal display device 100 of the present invention, the preferred lower limit of the content of above-mentioned filler
It is 70 parts by weight for 10 parts by weight, the upper limit preferably.By making the content of above-mentioned filler be more than 10 parts by weight, so that carrying
The effect of high adhesiveness etc. is more excellent.By making the content of above-mentioned filler be below 70 parts by weight, so that gained will not be made
The viscosity of sealing material for liquid crystal display device is too high and makes coating more excellent.The preferred lower limit of the content of above-mentioned filler
It is 60 parts by weight for 20 parts by weight, the preferred upper limit.
The sealing material for liquid crystal display device of the present invention preferably comprises silane coupler.Above-mentioned silane coupler mainly has
It is used as the effect of the bonding additives for making the good bondings such as sealant and substrate.
As above-mentioned silane coupler, from make with the excellent effect of the cementability raising of substrate etc., can by with solidification
Property resin be chemically bonded to suppress that curable resin flows out into liquid crystal in terms of set out, be adapted to use such as 3- aminopropans
Base trimethoxy silane, 3-mercaptopropyi trimethoxy silane, 3- glycidoxypropyltrime,hoxysilanes, 3- isocyanates
Propyl trimethoxy silicane etc..These silane couplers both can be used alone, can also and with two or more.
In the parts by weight of sealing material for liquid crystal display device 100 of the present invention, the content of above-mentioned silane coupler it is preferred
Lower limit is that 0.1 parts by weight, the upper limit preferably are 10 parts by weight.By making the content of above-mentioned silane coupler be the scope, so that
Suppress the generation of liquid crystal pollution, and make the effect of raising cementability more excellent.The content of above-mentioned silane coupler is more preferably
Lower limit be that 0.3 parts by weight, the preferred upper limit are 5 parts by weight.
The sealing material for liquid crystal display device of the present invention can contain opacifier.By containing above-mentioned opacifier, so that originally
The sealing material for liquid crystal display device of invention can be suitable as shading sealant.
As above-mentioned opacifier, black such as iron oxide, titanium, nigrosine, Cyanine Black, fullerene, carbon black, resin quilt can be enumerated
Cover type carbon black etc..Wherein, preferably titanium is black.
It is the average transmittance with the light for 300~800nm of wavelength Comparatively speaking for ultraviolet range that above-mentioned titanium is black
Nearby, it is particularly the higher material of the transmissivity of 370~450nm of wavelength light.That is, black above-mentioned titanium is by fully covering visible
The light of the wavelength in light region and to the present invention sealing material for liquid crystal display device assign light-proofness, and on the other hand have make purple
The opacifier for the property that the light of the wavelength of outside line areas adjacent is passed through.It is used as institute in the sealing material for liquid crystal display device of the present invention
The high material of the opacifier contained, preferably insulating properties, titanium is black to be also adaptable as the high opacifier of insulating properties.
Above-mentioned titanium is black also to play sufficient effect even if non-surface treated, and surface can also be used to have through coupling agent etc.
The treated titanium of machine composition is black；The inorganic constituents such as silicon, titanium oxide, germanium oxide, aluminum oxide, zirconium oxide, magnesia are oxidized to be coated to
The titanium surface-treated titanium such as black it is black.Wherein, in terms of it further can improve insulating properties, preferably handled with organic principle
The titanium crossed is black.
In addition, using containing manufactured by the black sealing material for liquid crystal display device of the invention as opacifier of above-mentioned titanium
Liquid crystal display cells have a sufficient light-proofness, thus unglazed spill can be realized and with high-contrast and with excellent
The liquid crystal display cells of display quality of image.
As black middle the commercially available product of above-mentioned titanium, it (is three that can enumerate such as 12S, 13M, 13M-C, 13R-N, 14M-C
Water chestnut Materials Co., Ltd system), Tilack D (red fringe chemical conversion company system) etc..
The preferred lower limit of the black specific surface area of above-mentioned titanium is 13m2/ g, the upper limit preferably are 30m2/ g, preferred lower limit
For 15m2/ g, the preferred upper limit are 25m2/g。
In addition, it is 3 Ω cm that the preferred lower limit of the black volume resistance of above-mentioned titanium, which is 0.5 Ω cm, the upper limit preferably, more
It is preferred that lower limit be that 1 Ω cm, the preferred upper limit are 2.5 Ω cm.
As long as the primary particle size of above-mentioned opacifier for the distance between the substrate of liquid crystal display cells below, then have no special limit
It is fixed, but preferred lower limit is that 1nm, the upper limit preferably are 5000nm.By making the primary particle size of above-mentioned opacifier be the scope, from
And on the premise of coating of sealing material for liquid crystal display device of gained etc. is deteriorated light-proofness can be made more excellent.On
The preferred lower limit for stating the primary particle size of opacifier is that 5nm, the preferred upper limit are 200nm, and further preferred lower limit is
10nm, the further preferred upper limit are 100nm.
It is explained, the primary particle size of above-mentioned opacifier can use NICOMP380ZLS (PARTICLE SIZING
SYSTEMS company systems) and above-mentioned opacifier is measured after being scattered in solvent (water, organic solvent etc.).
In the parts by weight of sealing material for liquid crystal display device 100 of the present invention, the preferred lower limit of the content of above-mentioned opacifier
It is 80 parts by weight for 5 parts by weight, the upper limit preferably.It is the scope by making the content of above-mentioned opacifier, so that the liquid of gained
Light-proofness is more excellent in the state of intensity of the crystal display element sealant after illustrative, cementability and the solidification for remaining excellent
It is different.The preferred lower limit of the content of above-mentioned opacifier is that 10 parts by weight, the preferred upper limit are 70 parts by weight, further preferably
Lower limit be that 30 parts by weight, the further preferred upper limit are 60 parts by weight.
As the method for the sealing material for liquid crystal display device of the manufacture present invention, it can enumerate for example：Using homogenous disperse machine,
The mixers such as homogeneous mixer, universal mixer, planetary-type mixer, kneader, three-roller by curable resin, the present invention
Method that the additive such as optical free radical polymerization initiator and the silane coupler that is added as needed on is mixed etc..
The sealing material for liquid crystal display device of the present invention is determined using E types viscosimeter under conditions of 25 DEG C, 1rpm to be obtained
The preferred lower limit of viscosity be that 100,000 mPas, the upper limit preferably are 600,000 mPas.By making above-mentioned viscosity be the scope,
So that the coating of the sealing material for liquid crystal display device of gained is excellent.The preferred lower limit of above-mentioned viscosity is 150,000
MPas, the preferred upper limit are 450,000 mPas.
By coordinating electrically conductive microparticle in the sealing material for liquid crystal display device of the present invention, led up and down so as to manufacture
Logical material.The conductive material up and down of such a sealing material for liquid crystal display device containing the present invention and electrically conductive microparticle is also this hair
It is one of bright.
As above-mentioned electrically conductive microparticle, metal ball can be used, conductive metal layer is formed with the surface of resin particle
Electrically conductive microparticle etc..Wherein, the electrically conductive microparticle of conductive metal layer is formed with the surface of resin particle excellent because of resin particle
Different elasticity and the ground such as transparency carrier can not be damaged and be conductively connected, therefore be preferred.
The liquid crystal being made using the sealing material for liquid crystal display device of the present invention or the conductive material up and down of the present invention
It is also one of present invention to show element.
As the method for the liquid crystal display cells of the manufacture present invention, it is adapted to use liquid crystal dripping process.Specifically, it can arrange
The method that citing such as has following process：In the glass substrate with electrodes such as ito thin films, polyethylene terephthalate base
The liquid crystal display cells of the present invention are coated with a substrate in 2 substrates such as plate with modes such as silk-screen printing, distributor coatings
The process for forming the seal pattern of frame-shaped with sealant etc.；It is uncured in the sealing material for liquid crystal display device of the present invention etc.
The tiny droplets of liquid crystal are added dropwise to the work of the inframe, under vacuo overlapping another substrate of the seal pattern for being coated on substrate under state
Sequence；The light such as the seal pattern partial illumination ultraviolet to the sealing material for liquid crystal display device etc. of the present invention and make sealant pre- solid
The process of change；And the sealant after precuring is heated and makes the process of its main solidification.
Invention effect
According to the present invention it is possible to which it is excellent and can suppress the sealing used for liquid crystal display element of liquid crystal pollution to provide photo-curable
Agent.In addition, according to the present invention it is possible to providing the conductive material up and down and liquid being made using the sealing material for liquid crystal display device
Crystal display element.
Embodiment
Embodiment is exemplified below the present invention is further described in detail, but the present invention is not limited to these implementations
Example.
(embodiment 1~7, comparative example 1~4)
According to the match ratio described in table 1, by each materials'use planetary stirring machine, (THINKY company systems " practice too by deaeration
Youth ") mixed after, reuse three-roller and mixed, thus prepare embodiment 1~7, each liquid crystal display of comparative example 1~4
Element sealant.
<Evaluate>
Following evaluation is carried out to each sealing material for liquid crystal display device of gained in embodiment and comparative example.As a result such as table
Shown in 1.
(photo-curable)
To be scattered in spacer particulate (ponding chemical industrial company system, " Micro-Pearl SI-H050 ") 1 parts by weight
Dispersion in embodiment and comparative example obtained by the parts by weight of each sealing material for liquid crystal display device 100 of gained is coated on glass base
On plate, the glass substrate of overlapping identical size, then, uses 10 seconds 100mW/ of metal halide light irradiation on the substrate
cm2Light, be fabricated to photo-curable test film.Light irradiation is with the situation without edge filter and has below 380nm light cutoff filters
2 patterns of situation of piece are carried out, and make 3 test films respectively to each pattern.Using infrared spectroscopy device, (BIORAD is public
Department's system, " FTS3000 "), variable quantity of the peak from (methyl) acryloyl group before and after light irradiation is determined, photocuring is thus carried out
The evaluation of property.The situation for reducing more than 95% from the peak of (methyl) acryloyl group later in light irradiation is set to " ◎ ", will be in light
Irradiation reduces more than 80% from the peak of (methyl) acryloyl group later and the situation less than 95% is set to "○", will be after light irradiation
Peak from (methyl) acryloyl group reduces more than 70% and the situation less than 80% is set to " △ ", by coming from after light irradiation
The situation of the reduction less than 70% at the peak of (methyl) acryloyl group is set to "×", and photo-curable is evaluated.
It is explained, variable quantity of the peak from (methyl) acryloyl group before and after light irradiation is taken to be obtained by 3 pieces of test films
The average value arrived.
(liquid crystal pollution)
Disperse spacer in the parts by weight of each sealing material for liquid crystal display device 100 of gained in embodiment and comparative example micro-
Grain (ponding chemical industrial company system, " Micro-Pearl SI-H050 ") 1 parts by weight, then the dispersion of thus gained is pressed
2 are coated on the alignment films and transparent electricity after rubbed using distributor for the mode of 1mm frame-shaped according to as line width
On a substrate in the substrate of pole.
Then, be added dropwise in the whole face of inframe of the sealant of the substrate with transparency electrode coating of liquid crystalline (Chisso company systems,
" JC-5004LA ") tiny droplets, fit immediately another carry transparency electrode substrate, using metal halide lamp to sealing
Agent partial illumination 100mW/cm2Light 10 seconds, make sealant cures, then heat 1 hour with 120 DEG C, obtain liquid crystal display cells.
Light irradiation is with the situation without edge filter and has 2 patterns of situation of below 380nm edge filters to carry out, and to each
Pattern makes 3 pieces of liquid crystal display cells respectively.
To the liquid crystal display cells of gained, reached with visual confirmation close after 60 DEG C of states for applying 1000 hours voltage
The liquid crystal pollution sealed near agent.
Liquid crystal pollution is judged using the irregular colour of 3 pieces of liquid crystal display cells, according to the degree of irregular colour, will be owned
Liquid crystal display cells in all the situations without irregular colour be set to " ◎ ", will slightly have at least 1 piece liquid crystal display cells
The situation of irregular colour is set to "○", and the situation for having a little irregular colour at least 1 piece liquid crystal display cells is set into " △ ",
The situation for there are many irregular colours at least 1 piece liquid crystal display cells is set to "×", liquid crystal pollution is evaluated.
It is explained, is evaluated as " ◎ ", the liquid crystal display cells of "○" are the level having no problem completely in practical.
[table 1]
Industrial applicability
According to the present invention it is possible to which it is excellent and can suppress the sealing used for liquid crystal display element of liquid crystal pollution to provide photo-curable
Agent.In addition, according to the present invention it is possible to providing the conductive material up and down and liquid being made using the sealing material for liquid crystal display device
Crystal display element.
Claims (5)
1. a kind of sealing material for liquid crystal display device, it is characterised in that it is drawn containing curable resin and optical free radical polymerization
The sealing material for liquid crystal display device of agent is sent out,
The optical free radical polymerization initiator contains the change shown in compound and/or following formula (1-2) shown in following formula (1-1)
Compound,
In formula (1-1), X represents that the alkyl of carbon number 1~8 or at least one hydrogen of cyclopenta ring can be replaced by methyl or ethyl
2- cyclopentyl ethyls, R represents methyl or ethyl,
In formula (1-2), Y represents that the alkyl of carbon number 2~8 or at least one hydrogen of cyclopenta ring can be replaced by methyl or ethyl
2- cyclopentyl ethyls, R represents methyl or ethyl.
2. sealing material for liquid crystal display device according to claim 1, it is characterised in that optical free radical polymerization initiator contains
There is the compound shown in following formula (2),
3. sealing material for liquid crystal display device according to claim 1 or 2, it is characterised in that contain opacifier.
4. conductive material above and below one kind, it is characterised in that contain the sealing used for liquid crystal display element described in claim 1,2 or 3
Agent and electrically conductive microparticle.
5. a kind of liquid crystal display cells, it is characterised in that be used for liquid crystal display element close described in usage right requirement 1,2 or 3
Envelope agent or claim 4 described in conductive material up and down and be made.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2015201156 | 2015-10-09 | ||
| JP2015-201156 | 2015-10-09 | ||
| PCT/JP2016/077419 WO2017061255A1 (en) | 2015-10-09 | 2016-09-16 | Sealing agent for liquid crystal display elements, vertically conducting material and liquid crystal display element |
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|---|---|
| CN107250904A true CN107250904A (en) | 2017-10-13 |
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| CN201680010544.3A Pending CN107250904A (en) | 2015-10-09 | 2016-09-16 | Sealing material for liquid crystal display device, up and down conductive material and liquid crystal display cells |
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| JP (1) | JP6126756B1 (en) |
| KR (1) | KR102649401B1 (en) |
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| CN110168441B (en) * | 2017-05-08 | 2022-07-29 | 积水化学工业株式会社 | Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element |
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|---|---|---|---|---|
| JP2009227955A (en) * | 2008-02-25 | 2009-10-08 | Jsr Corp | Curable composition, liquid crystal sealant, and liquid crystal display element |
| CN101891845A (en) * | 2010-07-15 | 2010-11-24 | 常州强力电子新材料有限公司 | Application of carbazole oxime ester compound serving as photoinitiator in photopolymerisable acrylate composition |
| CN102020727A (en) * | 2010-11-23 | 2011-04-20 | 常州强力先端电子材料有限公司 | Pyrazole oxime ester photoinitiator with high photosensibility, preparation method and application thereof |
| CN103305133A (en) * | 2013-06-18 | 2013-09-18 | 北京京东方光电科技有限公司 | Frame sealing glue and preparation method thereof as well as liquid crystal display panel and liquid display |
| WO2015152030A1 (en) * | 2014-03-31 | 2015-10-08 | 積水化学工業株式会社 | Sealing agent for liquid crystal dropping methods, vertically conducting material and liquid crystal display element |
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| 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 |
| KR100906926B1 (en) | 2001-05-16 | 2009-07-10 | 세키스이가가쿠 고교가부시키가이샤 | Curing Resin Composition and Sealants and End-Sealing Materials for Displays |
| CN104981732B (en) * | 2013-03-06 | 2017-05-24 | 积水化学工业株式会社 | Sealing agent for liquid crystal dropping methods, vertically conducting material, and liquid crystal display element |
| JP5685346B1 (en) * | 2013-05-15 | 2015-03-18 | 積水化学工業株式会社 | Liquid crystal dropping method sealing agent, vertical conduction material, and liquid crystal display element |
-
2016
- 2016-09-16 JP JP2016560845A patent/JP6126756B1/en active Active
- 2016-09-16 CN CN201680010544.3A patent/CN107250904A/en active Pending
- 2016-09-16 WO PCT/JP2016/077419 patent/WO2017061255A1/en active Application Filing
- 2016-09-16 KR KR1020177023894A patent/KR102649401B1/en active IP Right Grant
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009227955A (en) * | 2008-02-25 | 2009-10-08 | Jsr Corp | Curable composition, liquid crystal sealant, and liquid crystal display element |
| CN101891845A (en) * | 2010-07-15 | 2010-11-24 | 常州强力电子新材料有限公司 | Application of carbazole oxime ester compound serving as photoinitiator in photopolymerisable acrylate composition |
| CN102020727A (en) * | 2010-11-23 | 2011-04-20 | 常州强力先端电子材料有限公司 | Pyrazole oxime ester photoinitiator with high photosensibility, preparation method and application thereof |
| CN103305133A (en) * | 2013-06-18 | 2013-09-18 | 北京京东方光电科技有限公司 | Frame sealing glue and preparation method thereof as well as liquid crystal display panel and liquid display |
| WO2015152030A1 (en) * | 2014-03-31 | 2015-10-08 | 積水化学工業株式会社 | Sealing agent for liquid crystal dropping methods, vertically conducting material and liquid crystal display element |
Also Published As
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|---|---|
| TWI707945B (en) | 2020-10-21 |
| WO2017061255A1 (en) | 2017-04-13 |
| KR20180064327A (en) | 2018-06-14 |
| KR102649401B1 (en) | 2024-03-19 |
| JP6126756B1 (en) | 2017-05-10 |
| TW201732012A (en) | 2017-09-16 |
| JPWO2017061255A1 (en) | 2017-10-05 |
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