CN110383159A - Sealing material for liquid crystal display device, upper and lower conductive material and liquid crystal display element - Google Patents
Sealing material for liquid crystal display device, upper and lower conductive material and liquid crystal display element Download PDFInfo
- Publication number
- CN110383159A CN110383159A CN201880016547.7A CN201880016547A CN110383159A CN 110383159 A CN110383159 A CN 110383159A CN 201880016547 A CN201880016547 A CN 201880016547A CN 110383159 A CN110383159 A CN 110383159A
- Authority
- CN
- China
- Prior art keywords
- liquid crystal
- crystal display
- methyl
- display device
- sealing material
- Prior art date
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 127
- 239000003566 sealing material Substances 0.000 title claims abstract description 56
- 239000004020 conductor Substances 0.000 title claims abstract description 12
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- 229920005989 resin Polymers 0.000 claims abstract description 20
- 239000011347 resin Substances 0.000 claims abstract description 20
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
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- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 45
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1339—Gaskets; Spacers; Sealing of cells
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Nonlinear Science (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Sealing Material Composition (AREA)
- Liquid Crystal (AREA)
- Polymerisation Methods In General (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
The present invention passes through the sealing material for liquid crystal display device containing curable resin and the optical free radical polymerization initiator comprising compound represented by following formula (1), photo-curable and the excellent sealing material for liquid crystal display device of low liquid crystal pollution are provided, further it is provided that using upper and lower conductive material and liquid crystal display element made of the sealing material for liquid crystal display device.In formula (1), R1Indicate hydrogen atom, the alkyl or alicyclic type hydrocarbon that carbon atom number is 1 or more and 10 straight-chains or branched below, R2Indicate heteroaryl, R3Expression carbon atom number is 1 or more and 6 alkyl or aryl below.
Description
Technical field
The present invention relates to the sealing material for liquid crystal display device that photo-curable and low liquid crystal pollution are excellent.In addition, this hair
It is bright to be related to using upper and lower conductive material and liquid crystal display element made of the sealing material for liquid crystal display device.
Background technique
Manufacturing method as the liquid crystal display element of liquid crystal display etc. in recent years, from pitch time (Takt
Time) shorten, using the optimization of amount of liquid crystal from the perspective of, using disclosed in patent document 1, patent document 2 it is such, adopt
" liquid crystal is referred to as with the photo-thermal containing curable resin, Photoepolymerizationinitiater initiater and thermal curing agents and with the sealant of curing type
The mode of dropwise addition engineering method ".
In liquid crystal drop processing method, rectangle is above formed by distributor in one of 2 pieces of substrates with electrode first
The seal pattern of shape.Next, the tiny droplets of liquid crystal are added drop-wise in the sealing frame of plate in the state that sealant is uncured,
It is overlapped under vacuum with another plate, to the light of sealing irradiation ultraviolet light etc., is temporarily solidified.Then heating is carried out to carry out formally
Solidification makes liquid crystal display element.The liquid crystal drop processing method becomes the mainstream of the manufacturing method of liquid crystal display element at present.
But the today popularized in the various removable movement machines with liquid crystal display panel such as mobile portable phone, portable game, machine
The miniaturization of device is the most desirable project.As the method for machine miniaturization, the narrow frame of liquid crystal display part can be enumerated,
Such as configure under black substance black matrix" the position of sealing and (below, be also referred to as narrow frame design sometimes).This
Outside, in order to mitigate the destruction to liquid crystal display element, have studied the light irradiated when making sealant cures exposure reduce and
Remove the UV light of short wavelength.But since sealant is configured in the underface of black matrix" in narrow frame design, so such as
Fruit carries out liquid crystal drop processing method, then the light irradiated when making sealant photocuring is blocked, and light is difficult to reach the inside of sealant,
Especially the case where reducing the exposure of light, previous sealant cures are insufficient.If the solidification of sealant in this way is not filled
Point, then uncured sealant ingredient dissolves out in liquid crystal, there are problems that being easy to happen liquid crystal pollution.
As the method for inhibiting liquid crystal pollution, it is believed that in order to solidify sealant sufficiently, need to cooperate a large amount of light poly-
Close initiator.But the case where cooperating a large amount of Photoepolymerizationinitiater initiaters, have the Photoepolymerizationinitiater initiater itself and become liquid crystal pollution
The problem of reason.In addition, disclosing in patent document 3, cooperation has the highly sensitive light of specific structure poly- in the encapsulant
Close initiator.But the case where cooperating Photoepolymerizationinitiater initiater disclosed in Patent Document 3, it can not sufficiently inhibit liquid sometimes
Crystalline substance pollution.
Existing technical literature
Patent document
Patent document 1: Japanese Unexamined Patent Publication 2001-133794 Patent Document 2: International Publication No. 02/092718 is specially
Sharp document 3: International Publication No. 2012/002028
Summary of the invention
Subject to be solved by the invention
The object of the present invention is to provide the sealing material for liquid crystal display device that photo-curable and low liquid crystal pollution are excellent.This
Outside, the object of the present invention is to provide using made of the sealing material for liquid crystal display device, conductive material and liquid crystal display are first up and down
Part.
The means to solve the problem
The present invention is the sealing material for liquid crystal display device containing curable resin and optical free radical polymerization initiator, described
Optical free radical polymerization initiator contains compound represented by following formula (1).
In formula (1), R1Indicate the alkyl or alicyclic ring of hydrogen atom, carbon atom number 1 or more 10 straight-chain or branched below
Formula alkyl, R2Indicate heteroaryl, R3Indicate the alkyl or aryl below of carbon atom number 1 or more 6.
The present invention is specifically described below
It was surprisingly found by the present inventors that by cooperating the compound with specific structure to draw as optical free radical polymerization
Agent is sent out, photo-curable and the excellent sealing material for liquid crystal display device of low liquid crystal pollution can be obtained, thereby completing the present invention.
Sealing material for liquid crystal display device of the invention is especially manufacturing narrow frame design by liquid crystal drop processing method
The low situation of the exposure in liquid crystal display element time can also not increase the content of the optical free radical polymerization initiator
In the case of sufficiently solidify.
Sealing material for liquid crystal display device of the invention contains optical free radical polymerization initiator.
The optical free radical polymerization initiator contains compound represented by the formula (1).By containing the formula (1) institute
The compound of expression is as optical free radical polymerization initiator, the photo-curable of sealing material for liquid crystal display device of the invention and low
Liquid crystal pollution is excellent.
As R in the formula (1)1The alkyl of represented carbon atom number 1 or more and 10 straight-chain or branched below,
Such as methyl, ethyl, n-propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, tert-butyl, neopentyl, isoamyl can be enumerated
Base, sec-amyl, 3- amyl, tertiary pentyl, n-hexyl, isohesyl, n-heptyl, n-octyl etc..
As R in the formula (1)1Represented alicyclic type hydrocarbon can enumerate such as cyclopropyl, cyclobutyl, ring penta
Base, cyclohexyl, cyclopentyl-methyl, cyclohexyl methyl etc..
The R1, it is preferably especially the alkyl below of carbon atom number 3 or more 6 or ester ring type hydrocarbon from sterically hindered viewpoint
Base, more preferable isopentyl, isohesyl, cyclopenta, and then preferred isopentyl.
As R in the formula (1)2Represented heteroaryl can enumerate such as 1- pyrrole radicals, 2- pyrrole radicals, 3- pyrrole
Cough up base, pyrazinyl, 2- pyridyl group, 3- pyridyl group, 4- pyridyl group, 1- indyl, 2- indyl, 3- indyl, 4- indyl, 5-
Indyl, 6- indyl, 7- indyl, 1- isoindolyl, 2- isoindolyl, 3- isoindolyl, 4- isoindolyl, 5- iso-indoles
Base, 6- isoindolyl, 7- isoindolyl, 2- furyl, 3- furyl, 2- benzofuranyl, 3- benzofuranyl, 4- benzo furan
It mutters base, 5- benzofuranyl, 6- benzofuranyl, 7- benzofuranyl, 1- isobenzofuran-base, 3- isobenzofuran-base, 4-
Isobenzofuran-base, 5- isobenzofuran-base, 6- isobenzofuran-base, 7- isobenzofuran-base, quinolyl, 3- quinolyl, 4-
Quinolyl, 5- quinolyl, 6- quinolyl, 7- quinolyl, 8- quinolyl, 1- isoquinolyl, 3- isoquinolyl, 4- isoquinolyl,
5- isoquinolyl, 6- isoquinolyl, 7- isoquinolyl, 8- isoquinolyl, 2- quinoxalinyl, 5- quinoxalinyl, 6- quinoxalinyl,
1- carbazyl, 2- carbazyl, 3- carbazyl, 4- carbazyl, 9- carbazyl etc..
Especially, the R2Preferably have oxygen atom as heteroatomic heteroaryl, more preferably 2- benzofuranyl,
3- benzofuranyl, 4- benzofuranyl, 5- benzofuranyl, 6- benzofuranyl, 7- benzofuran, and then more preferably 2- benzene
And furyl.
As R in the formula (1)3The represented alkyl below of carbon atom number 1 or more 6, can enumerate such as methyl,
Ethyl, n-propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, tert-butyl, neopentyl, isopentyl, sec-amyl, 3- amyl, uncle
Amyl, n-hexyl, isohesyl etc..
As R in the formula (1)3Represented aryl can be enumerated such as benzyl.
Especially, the R3Preferably carbon atom number is 1 or more 6 alkyl below, more preferably methyl, ethyl, positive third
Base, and then more preferably methyl.
The optical free radical polymerization initiator contains following formula (2) institute preferably as compound represented by the formula (1)
Compound represented by the compound and/or following formula (3) of expression.By containing compound represented by following formula (2) and/or
Compound represented by following formula (3), the photo-curable of the sealing material for liquid crystal display device enabled to and low liquid crystal are dirty
Metachromia is more excellent.Especially, further preferably compound represented by following formula (2) is as chemical combination represented by the formula (1)
Object.
Compound represented by the formula (1), reactivity is very excellent, so even if use level is on a small quantity, can also to make
Obtained sealing material for liquid crystal display device is high sensitivity, and photo-curable is excellent.
Specifically, the content of compound represented by the formula (1) relative to 100 parts by weight of curable resin it is preferred under
It is limited to 0.1 parts by weight, preferred upper limit is 5 parts by weight.If making 0.1 weight of content of compound represented by the formula (1)
Part or more, then the sealing material for liquid crystal display device photo-curable enabled to is more excellent.By keeping the formula (1) represented
Compound content be 5 parts by weight hereinafter, the low liquid crystal pollution of the sealing material for liquid crystal display device enabled to more
It is excellent.It is 3 parts by weight that the more preferable lower limit of the content of compound represented by the formula (1), which is 1 parts by weight, the more preferable upper limit,.
Sealing material for liquid crystal display device of the invention contains curable resin.
The curable resin preferably comprises (methyl) acryl compound.
As (methyl) acryl compound, such as (methyl) acrylic acid and the change with hydroxyl can be enumerated
Close epoxy obtained from (methyl) acrylate compounds, (methyl) acrylic acid obtained from object reacts are reacted with epoxide
Amino first obtained from (methyl) acrylate, isocyanate compound are reacted with (methyl) acrylic acid derivative with hydroxyl
Perester radical (methyl) acrylate etc..Especially preferred epoxy (methyl) acrylate.In addition, (methyl) polyacryl
Object is closed, due to reactive high it is preferred that having 2 or more (methyl) acryloyl groups in molecule.
Furthermore in this specification, " (methyl) acryloyl group " refers to acryloyl group or methylacryloyl, described
" (methyl) acryl compound " refers to the compound with (methyl) acryloyl group, and " (methyl) acryloyl group " refers to
Acryloyl group or methylacryloyl.In addition, " (methyl) acrylate " refers to acrylate or methacrylate.Into
And " epoxy (methyl) acrylate " refers to that all epoxy groups in epoxide are reacted with (methyl) acrylic acid and obtained
Compound.
As the monofunctional compound in (methyl) acrylate compounds, such as (methyl) propylene can be enumerated
Sour methyl esters, (methyl) ethyl acrylate, (methyl) propyl acrylate, (methyl) n-butyl acrylate, (methyl) i-butyl
Ester, (methyl) tert-butyl acrylate, (methyl) 2-EHA, (methyl) n-octyl, (methyl) acrylic acid
Different monooctyl ester, the different nonyl ester of (methyl) acrylic acid, (methyl) isodecyl acrylate, (methyl) lauryl acrylate, (methyl) propylene
The different nutmeg base ester of acid, (methyl) stearyl acrylate base ester, (methyl) acrylic acid 2- hydroxy methacrylate, (methyl) acrylic acid 2- hydroxyl
Propyl ester, (methyl) acrylic acid 2- hydroxybutyl, (methyl) propylene 4 hydroxybutyric acid ester, (methyl) cyclohexyl acrylate, (methyl)
Isobornyl acrylate, (methyl) acrylic acid double cyclopentenyl ester, (methyl) benzyl acrylate, (methyl) acrylic acid 2- methoxyl group
Ethyl ester, (methyl) acrylic acid 2- ethoxy ethyl ester, (methyl) acrylic acid 2- butoxyethyl, (methyl) acrylic acid 2- phenoxy group second
Ester, methoxy ethyl glycol (methyl) acrylate, methoxy poly (ethylene glycol) (methyl) acrylate, phenoxy group diethylene glycol (first
Base) acrylate, phenoxy group polyethylene glycol (methyl) acrylate, (methyl) tetrahydrofurfuryl acrylate, ethyl carbitol (first
Base) acrylate, (methyl) acrylic acid 2,2,2- trifluoro ethyl ester, (methyl) acrylic acid 2,2,3,3- tetrafluoro propyl ester, (methyl) third
Olefin(e) acid 1H, 1H, 5H- octafluoro pentyl ester, acid imide (methyl) acrylate, (methyl) dimethylaminoethyl acrylate, (methyl) third
Olefin(e) acid lignocaine ethyl ester, 2- (methyl) acrylyl oxy-ethyl succinic acid, 2- (methyl) acrylyl oxy-ethyl hexahydro O-phthalic
Acid esters, 2- (methyl) acrylyl oxy-ethyl 2- hydroxypropyl phthalate, 2- (methyl) acryloyl-oxyethyl phosphate,
Glycidyl (meth) acrylate etc..
In addition, such as 1,3- fourth can be enumerated as 2 functional compounds in (methyl) acrylate compounds
Glycol two (methyl) acrylate, 1,4- butanediol two (methyl) acrylate, 1,6-hexylene glycols two (methyl) acrylate, 1,
9- nonanediol two (methyl) acrylate, 1,10- decanediol two (methyl) acrylate, ethylene glycol two (methyl) acrylate,
Diethylene glycol two (methyl) acrylate, tetraethylene glycol two (methyl) acrylate, polyethylene glycol two (methyl) acrylate, 2-
Two (methyl) acrylate of normal-butyl -2- ethyl -1,3- propylene glycol, dipropylene glycol two (methyl) acrylate, tripropylene glycol two
(methyl) acrylate, polypropylene glycol (methyl) acrylate, neopentyl glycol two (methyl) acrylate, ethyleneoxide addition are double
Phenol A bis- (methyl) acrylate, propylene oxide addition bisphenol-A two (methyl) acrylate, two (first of ethyleneoxide addition Bisphenol F
Base) acrylate, dihydroxymethyl dicyclopentadienyl two (methyl) acrylate, ethylene-oxide-modified isocyanuric acid two (methyl)
Acrylate, 2- hydroxyl -3- (methyl) acryloxypropyl (methyl) acrylate, carbonate diol two (methyl) acrylic acid
Ester, polyetherdiol two (methyl) acrylate, polyester-diol two (methyl) acrylate, polycaprolactone glycol two (methyl) propylene
Acid esters, polybutadiene diol two (methyl) acrylate etc..
In addition, such as three can be enumerated as the above compound of 3 functions in (methyl) acrylate compounds
Hydroxymethyl-propane three (methyl) acrylate, ethyleneoxide addition trimethylolpropane tris (methyl) acrylate, propylene oxide
Addition trimethylolpropane tris (methyl) acrylate, caprolactone modification trimethylolpropane tris (methyl) acrylate, epoxy
Ethane addition isocyanuric acid three (methyl) acrylate, glycerol three (methyl) acrylate, three (first of propylene oxide addition glycerol
Base) acrylate, pentaerythrite three (methyl) acrylate, three (methyl) acrylyl oxy-ethyl phosphates, two (trihydroxy methyls)
Propane four (methyl) acrylate, pentaerythrite four (methyl) acrylate, dipentaerythritol five (methyl) acrylate, two seasons
Penta tetrol six (methyl) acrylate etc..
As the epoxy (methyl) acrylate, can enumerate for example presses epoxide and (methyl) acrylic acid
Obtained from being reacted in the presence of basic catalyst according to usual method etc..
As the raw material epoxide for synthesizing the epoxy (methyl) acrylate, such as bis-phenol can be enumerated
A type ring oxygen compound, bisphenol F type epoxy compound, bisphenol S type epoxy compound, the oxidation of 2,2 '-diallyl bisphenol type rings
Close object, A Hydrogenated Bisphenol A type ring oxygen compound, propylene oxide addition bisphenol A type epoxy compound, resorcinol type ring oxygen compound,
Biphenyl type epoxy compound, thioether-type epoxide, diphenyl ether type ring oxygen compound, dicyclopentadiene type epoxy chemical combination
Object, naphthalene type ring oxygen compound, phenol novolak-type epoxy compound, ortho cresol novolak type epoxide, two rings penta
Diene novolak type epoxy compounds, biphenyl novolak type epoxy compounds, naphthol novolac type epoxy compound, contracting
Water glyceramine type ring oxygen compound, alkyl polyols type ring oxygen compound, modified rubber type ring oxygen compound, glycidyl esters
Compound etc..
As the commercially available product in the bisphenol A type epoxy compound, such as jER828EL, jER1004 can be enumerated (
For society, Mitsubishi Chemical system), エ ピ Network ロ Application 850CRP (DIC society system) etc..
As the commercially available product in the bisphenol F type epoxy compound, can enumerate such as jER806, jER4004 (is
Society, Mitsubishi Chemical system) etc..
As commercially available in the bisphenol S type epoxy compound, such as エ ピ Network ロ Application EXA1514 can be enumerated
(DIC society system) etc..
As commercially available in described 2,2 '-diallyl bisphenol type ring oxygen compounds, such as RE- can be enumerated
810NM (Japanese Chemical Drug Society's system) etc..
As commercially available in the A Hydrogenated Bisphenol A type ring oxygen compound, such as エ ピ Network ロ Application can be enumerated
EXA7015 (DIC society system) etc..
As commercially available in the propylene oxide addition bisphenol A type epoxy compound, such as EP- can be enumerated
4000S (ADEKA society system) etc..
As the commercially available product in the resorcinol type ring oxygen compound, such as EX-201 (Na ガ セ ケ can be enumerated
System テ ッ Network ス society system) etc..
As the commercially available product in the biphenyl type epoxy compound, such as jER YX-4000H (Mitsubishi can be enumerated
Learn society's system) etc..
As the commercially available product in the thioether-type epoxide, can enumerating such as YSLV-50TE, (gold is lived by Nippon Steel
Chemical society's system) etc..
As the commercially available product in the diphenyl ether type ring oxygen compound, such as YSLV-80DE (Nippon Steel can be enumerated
Firmly aurification society system) etc..
As the commercially available product in the dicyclopentadiene type epoxy compound, such as EP-4088S (ADEKA can be enumerated
Society's system) etc..
As the commercially available product in the naphthalene type ring oxygen compound, such as エ ピ Network ロ Application HP4032, エ ピ can be enumerated
Network ロ Application EXA-4700 (being DIC society system) etc..
As the commercially available product in the phenol novolak-type epoxy compound, such as エ ピ Network ロ Application N- can be enumerated
770 (DIC society systems) etc..
As the commercially available product in the ortho cresol novolak type epoxide, can enumerate for example, エ ピ Network ロ
Application N-670-EXP-S (DIC society system) etc..
As the commercially available product in the dicyclopentadiene novolac type ring oxygen compound, such as エ ピ Network can be enumerated
ロ Application HP7200 (DIC society system) etc..
As the commercially available product in the biphenyl novolak type epoxy compounds, such as NC-3000P (day can be enumerated
This chemical drug society system) etc..
Commercially available product in the naphthol novolac type epoxy compound can enumerate such as ESN-165S (Nippon Steel
Firmly aurification society system) etc..
As the commercially available product in the glycidyl amine epoxy compound, such as jER630 (Mitsubishi can be enumerated
Learn society's system), エ ピ Network ロ Application 430 (DIC society system), TETRAD-X (ガ ス chemistry society, Mitsubishi system) etc..
As the commercially available product in the alkyl polyols type ring oxygen compound, such as ZX-1542 (Nippon Steel can be enumerated
Firmly aurification society system), エ ピ Network ロ Application 726 (DIC society system), エ Port ラ イ ト 80MFA (chemistry society, common prosperity society system), デ ナ コ ー
Le EX-611 (Na ガ セ ケ system テ ッ Network ス society system) etc..
As the commercially available product in the modified rubber type ring oxygen compound, can enumerate for example, YR-450, YR-207
(being that aurification society system is lived by Nippon Steel), エ ポ リ ー De PB (ダ イ セ Le society system) etc..
As the commercially available product in the glycidyl ester compounds, can enumerate for example, デ Na U ー Le EX-147
(Na ガ セ ケ system テ ッ Network ス society system) etc..
As other commercially available products in the epoxide, can enumerate for example, YDC-1312, YSLV-80XY,
YSLV-90CR (being that aurification society system is lived by Nippon Steel), XAC4151 (society, Asahi Chemical Industry system), jER1031, jER1032 (are three
Water chestnut chemistry society system), EXA-7120 (DIC society system), TEPIC (Nissan Chemical society system) etc..
As the commercially available product in the epoxy (methyl) acrylate, can enumerate for example, EBECRYL860,
EBECRYL3200、EBECRYL3201、EBECRYL3412、EBECRYL3600、EBECRYL3700、EBECRYL3701、
EBECRYL3702, EBECRYL3703, EBECRYL3800, EBECRYL6040, EBECRYL RDX63182 (are ダ イ セ
Le オ Le ネ Network ス society system), EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020 (be in new
Village's chemical industry corporation system), エ Port キ シ エ ス テ Le M-600A, エ Port キ シ エ ス テ Le 40EM, エ Port キ シ エ ス テ Le
70PA、エポキシエステル200PA、エポキシエステル80MFA、エポキシエステル3002M、エポキ
シエステル3002A、エポキシエステル1600A、エポキシエステル3000M、エポキシエステル
3000A, エ Port キ シ エ ス テ Le 200EA, エ Port キ シ エ ス テ Le 400EA (being chemistry society, common prosperity society system), デ Na U
ー Le ア Network リ レ ー ト DA-141, デ ナ コ ー Le ア Network リ レ ー ト DA-314, デ ナ コ ー Le ア Network リ レ ー ト DA-911 are (
For Na ガ セ ケ system テ ッ Network ス society system) etc..
Carbamate groups (methyl) acrylate, can be for example, by relative to 2 isocyanate group
1 equivalent of isocyanate compound makes have 2 equivalent of (methyl) acrylic acid derivative of hydroxyl in the tin based compound of catalytic amount
In the presence of react and obtain.
As the isocyanate compound, can enumerate for example, isophorone diisocyanate, 2,4- toluene two it is different
Cyanate, 2,6- toluene di-isocyanate(TDI), six methylene diisocyanate, trimethyl hexamethylene diisocyanate, diphenyl-methane-
4,4 '-diisocyanate (MDI), hydrogenation MDI, polymethylene polyphenyl base polyisocyanate, 1,5- naphthalene diisocyanate, norborneol
Alkane diisocyanate, xylylene diisocyanate (XDI), hydrogenation XDI, relies diacid two different at o-tolidine diisocyanate
Cyanate, triphenylmethane triisocyanate, three (isocyanatophenyl) thiophosphates, two methylene diisocyanate of durol
Ester, 1,6,11- hendecane triisocyanate etc..
In addition, can be used as the isocyanate compound for example, by ethylene glycol, propylene glycol, glycerol, sorbose
The polyalcohol of alcohol, trimethylolpropane, carbonate diol, polyetherdiol, polyester-diol, polycaprolactone glycol etc. is different with surplus
The isocyanate compound that chain obtained from cyanate esters reaction has been extended.
As described (methyl) acrylic acid derivative with hydroxyl, such as (methyl) acrylic acid 2- hydroxyl second can be enumerated
The commercially available products, second such as ester, (methyl) acrylic acid 2- hydroxypropyl acrylate, (methyl) acrylic acid 2- hydroxy butyl ester, (methyl) acrylic acid 4- hydroxy butyl ester
List (methyl) acrylic acid of the divalent alcohols such as glycol, propylene glycol, 1,3- propylene glycol, 1,3 butylene glycol, 1,4- butanediol, polyethylene glycol
List (methyl) acrylate of the trivalent alcohols such as ester, trimethylolethane, trimethylolpropane, glycerol or two (methyl) acrylic acid
The epoxies such as ester, bisphenol-a epoxy acrylate (methyl) acrylate etc..
As the commercially available product in the carbamate groups (methyl) acrylate, such as M-1100, M- can be enumerated
1200, M-1210, M-1600 (be East Asia synthesis society's system), EBECRYL210, EBECRYL220, EBECRYL230,
EBECRYL270、EBECRYL1290、EBECRYL2220、EBECRYL4827、EBECRYL4842、EBECRYL4858、
EBECRYL5129、EBECRYL6700、EBECRYL8402、EBECRYL8803、EBECRYL8804、EBECRYL8807、
EBECRYL9260 (is ダ イ セ Le オ Le ネ Network ス society), ア ー ト レ ジ Application UN-330, ア ー ト レ ジ Application SH-
500B、アートレジンUN-1200TPK、アートレジンUN-1255、アートレジンUN-3320HB、アートレジ
Application UN-7100, ア ー ト レ ジ Application UN-9000A, ア ー ト レ ジ Application UN-9000H (being industrial society system on root), 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 (being the village Xin Zhong chemical industry corporation system), AH-600, AI-600, AT-600,
UA-101I, UA-101T, UA-306H, UA-306I, UA-306T (being chemistry society, common prosperity society system) etc..
The curable resin, for the purpose for improving the obtained cementability of sealing material for liquid crystal display device it is preferred that
Also contain epoxide.As the epoxide, can enumerate for example as synthesizing above-mentioned epoxy (methyl)
Epoxide, part (methyl) acryloyl modified epoxy compound of the raw material of acrylate etc..
Furthermore part (methyl) acryloyl modified epoxy compound described in this specification refers to there is epoxy in 1 molecule
The compound of base and each 1 of (methyl) acryloyl group or more, can be for example, by making in 1 molecule with 2 or more epoxy groups
The PART EPOXY base of epoxide reacts to obtain with (methyl) acrylic acid.
The case where sealing material for liquid crystal display device of the invention contains the epoxide, preferably with (methyl) third
The mode that enoyl- and the ratio of epoxy group are 30:70~95:5 cooperates (methyl) acryl compound and the epoxidation
Close object.By making 30% or more the ratio of (methyl) acryloyl group, the sealing material for liquid crystal display device enabled to
Low liquid crystal pollution is more excellent.By making the ratio 95% of (methyl) acryloyl hereinafter, the liquid crystal display member enabled to
Part is more excellent with sealant cementability.
The curable resin preferably has-OH ,-NH- ,-NH in terms of inhibiting liquid crystal pollution2Equal hydrogen associativity
Unit.
Sealing material for liquid crystal display device of the invention can contain hot radical polymerization initiator.
As the hot radical polymerization initiator, can enumerate such as azo-compound, organic peroxide
It is formed.It is particularly preferred to (also be referred to as " polymeric azo sometimes below by the initiator that polymeric azo compound is formed
Initiator ").
Furthermore the polymeric azo initiator in this specification refers to azo group, (first can be made by being thermally generated
Base) the cured free radical of acryloyl group, number-average molecular weight be 300 or more compound.
The preferred lower limit of the number-average molecular weight of the polymeric azo initiator is 1000, preferred upper limit is 300,000.Pass through
Make the number-average molecular weight of the polymeric azo initiator in the range, can prevent from causing liquid crystal adverse effect, while more
It is readily mixed into curable resin.The more preferable lower limit of the number-average molecular weight of the polymeric azo initiator be 5000, into
And the more preferably upper limit is 100,000, more preferable lower limit is 10,000 and then the more preferably upper limit is 90,000.
Furthermore in this specification, the number-average molecular weight be by gel permeation chromatography (GPC) measurement obtain, through polyphenyl
The value that ethylene conversion is found out.As the pillar to convert when measuring number-average molecular weight by GPC through polystyrene, example can be enumerated
Such as Shodex LF-804 (Showa electrician society system).
As the polymeric azo initiator, can enumerate for example, make polyoxyalkylene or poly- diformazan via azo group
The multiple structures being combined into of the units such as radical siloxane.
As with the polymeric azo for making the multiple structures being combined into of the units such as polyoxyalkylene via the azo group
Initiator preferably has polyoxyethylene structure.As this polymeric azo initiator, can enumerate for example, 4,4 '-azos
The condensation polymer of two (4- cyanopentanoic acids) and ployalkylene glycol, 4,4 '-azos two (4- cyanopentanoic acid) and end have the poly- of amino
The condensation polymer etc. of dimethyl siloxane, specific examples thereof include such as VPE-0201, VPE-0401, VPE-0601, VPS-0501,
VPS-1001 (being Wako Pure Chemical Industries, Ltd.'s system) etc..
In addition, can enumerate V-65, V-501 (is pure with light as the example for not being high molecular azo-compound
Medicine industry society system) etc..
As the organic peroxide, such as ketone peroxide, ketal peroxide, hydroperoxides, mistake can be enumerated
Dialkyltin oxides base, peroxy esters, diacyl peroxides, peroxy dicarbonate etc..
The content of the hot radical polymerization initiator is relative to the 100 parts by weight preferred lower limit of curable resin
0.05 parts by weight, preferred upper limit are 10 parts by weight.It, can by making the content of the hot radical polymerization initiator in the range
Inhibit liquid crystal pollution caused by unreacted hot radical polymerization initiator, the thermosetting of obtained sealing material for liquid crystal display device
Property is more excellent.The more preferable lower limit of the content of the hot radical polymerization initiator is 0.1 parts by weight, the more preferable upper limit is 5 weights
Measure part.
Sealing material for liquid crystal display device of the invention preferably comprises hot-setter.
As the hot-setter, can enumerate for example, organic acid hydrazides, imdazole derivatives, amine compounds, multivalence phenol system
Compound, acid anhydrides etc..It is especially preferred to adapt to organic acid hydrazides.
As the organic acid hydrazides, can enumerate for example, sebacic dihydrazide, isophthalic dihydrazide, oneself two
Acid dihydrazide, acid dihydrazide etc..
Commercially available product in the organic acid hydrazides can enumerate such as SDH, ADH (being big tomb chemistry society system), ア ミ
キ ュ ア VDH, ア ミ キ ュ ア VDH-J, ア ミ キ ュ ア UDH, ア ミ キ ュ ア UDH-J (are monosodium glutamate Off ァ イ Application テ Network ノ
Society's system) etc..
The content of the hot-setter is 1 parts by weight, preferably relative to the 100 parts by weight preferred lower limit of curable resin
The upper limit is 50 parts by weight.More than 1 parts by weight of content by making the hot-setter, what is enabled to is used for liquid crystal display element
The thermosetting property of sealant is more excellent.By making 50 parts by weight of content of the hot-setter hereinafter, the liquid crystal enabled to
Show that the viscosity of element sealant will not become excessively high, coating is more excellent.The more preferable upper limit of the content of the hot-setter is
30 parts by weight.
Sealing material for liquid crystal display device of the invention is improved for viscosity, stress dispersion effect bring cementability changes
Kind, linear expansivity improves, the moisture-proof of solidfied material further increases etc. purpose and preferably comprise filler.
As the filler, such as silica, talcum, bead, asbestos, gypsum, diatomite, illiteracy can be enumerated
De- stone, bentonite, montmorillonite, sericite, atlapulgite, aluminium oxide, zinc oxide, iron oxide, magnesia, tin oxide, titanium oxide,
The inorganic fillers such as calcium carbonate, magnesium carbonate, magnesium hydroxide, aluminium hydroxide, aluminium nitride, silicon nitride, barium sulfate, calcium silicates, polyester
The organic fillers such as particle, polyurethane particulate, polyvinyl particle, acrylic polymer particle.
The preferred lower limit of the content of filler described in 100 parts by weight of sealing material for liquid crystal display device of the invention is 10
Parts by weight, preferred upper limit are 70 parts by weight.More than 10 parts by weight of content by making the filler, cementability can be made to change
It is more excellent to be apt to the effect waited.By making 70 parts by weight of content of the filler hereinafter, the liquid crystal display member enabled to
The viscosity of part sealant is not too high, and coating is more excellent.The more preferable lower limit of the content of the filler be 20 parts by weight,
The more preferable upper limit is 60 parts by weight.
Sealing material for liquid crystal display device of the invention preferably comprises silane coupling agent.The silane coupling agent mainly has
Act on the bonding additives of the good bondings such as sealant and plate.
As the silane coupling agent, due to the cementability improvement effect of plate etc. it is excellent, by with curable resin
Learn in conjunction with and be able to suppress curable resin and flow in liquid crystal, and it is preferable to use for example, 3- TSL 8330,3-
Mercaptopropyi trimethoxy silane, 3- (glycidoxy) propyl trimethoxy silicane, 3- isocyanate group propyl trimethoxy
Silane etc..
The preferred lower limit of the content of silane coupling agent described in 100 parts by weight of sealing material for liquid crystal display device of the invention
It is 0.1 parts by weight, preferred upper limit is 10 parts by weight.By making the content of the silane coupling agent in the range, it is able to suppress liquid
Crystalline substance pollution occurs, and keeps cementability improvement effect more excellent.The more preferable lower limit of the content of the silane coupling agent is 0.3 weight
Part, the more preferable upper limit are 5 parts by weight.
Sealing material for liquid crystal display device of the invention can also contain opacifier.By containing the opacifier, this hair
Bright sealing material for liquid crystal display device can be used as shading sealant and use well.
As the opacifier, it can enumerate that black such as iron oxide, titanium, nigrosine, ultramarine (cyanine) be black, fowler
Alkene, carbon black, resin-coated type carbon black etc..Particularly preferred titanium is black.
The titanium is black, be compared with the mean transmissivity of the light of 300~800nm of wavelength, near ultraviolet range, it is special
It is not the high substance of the transmitance of the light of 370~450nm of wavelength.I.e., the titanium is black, the light of the wavelength by will be seen that light region
Sufficiently masking can assign sealing material for liquid crystal display device light-proofness of the invention, and on the other hand it is that have to make ultraviolet light
The opacifier for the property that the light of the wavelength of areas adjacent penetrates.As what is contained in sealing material for liquid crystal display device of the invention
The high substance of opacifier, preferably insulating properties, the opacifier high as insulating properties, preferably titanium are black.
The titanium is black, even if not surface treated, can also play sufficient effect, but surface can be used and be coupled agent
The titanium that equal organic principles have been handled is black, surface has been coated silica, titanium oxide, germanium oxide, aluminium oxide, zirconium oxide, magnesia etc.
The black titanium that is equal, being surface treated of the titanium of inorganic constituents is black.Especially, the titanium handled by organic principle is black, is further mentioning
In terms of high-insulativity preferably.
In addition, containing the black sealing material for liquid crystal display device of the invention of the titanium used as opacifier and manufacturing
Liquid crystal display element has sufficient light-proofness, does not leak out light so can be realized, shows with high-resolution, excellent image
Show the liquid crystal display element of quality.
As the titanium it is black in commercially available product, can enumerate such as 12S, 13M, 13M-C, 13R-N, 14M-C (is three
Water chestnut マ テ リ ア Le society system), テ ィ ラ ッ Network D (Chi Miho be melted into society's system) etc..
The preferred lower limit of the black specific surface area of the titanium is 13m2/ g, preferred upper limit 30m2/ g, more preferable lower limit are
15m2/ g, the more preferable upper limit are 25m2/g。
In addition, the preferred lower limit of the black volume resistance of the titanium is 0.5 Ω cm, preferred upper limit is 3 Ω cm, more preferably
Lower limit is 1 Ω cm, the more preferable upper limit is 2.5 Ω cm.
The primary particle size of the opacifier, as long as the distance between the substrate of liquid crystal display element hereinafter, as long as it is not special
It limits, preferred lower limit 1nm, preferred upper limit 5000nm.By making the primary particle size of the opacifier in the range, Neng Gou
The coating etc. of obtained sealing material for liquid crystal display device keeps light-proofness more excellent in the case where not being deteriorated.The opacifier
The more preferable lower limit of primary particle size is 5nm, the more preferable upper limit is 200nm, and more preferable lower limit is 10nm, the more preferable upper limit is
100nm。
Furthermore NICOMP 380ZLS (PARTICLE SIZING can be used in the primary particle size of the opacifier
SYSTEMS society system), the opacifier is dispersed in measurement in solvent (water, organic solvent etc.).
The preferred lower limit of the content of opacifier described in 100 parts by weight of sealing material for liquid crystal display device of the invention is 5
Parts by weight, preferred upper limit are 80 parts by weight.It is more than 5 parts by weight of content by making the opacifier, obtained liquid crystal display
The light-proofness of element sealant is more excellent.By making 80 parts by weight of content of the opacifier hereinafter, obtained liquid crystal
Display element sealant to after plate adaptation, solidification intensity and drawing property it is more excellent.The content of the opacifier is more
Preferred lower limit is 10 parts by weight, the more preferable upper limit is 70 parts by weight, and more preferable lower limit is 30 parts by weight, the more preferable upper limit is 60 weights
Measure part.
Sealing material for liquid crystal display device of the invention can also contain stress moderator, reactivity dilution as needed
Agent, thixotropic agent, spacer (ス ペ ー サ ー), curing accelerator, defoaming agent, levelling agent, the additives such as polymerization inhibitor.
As the method for manufacturing sealing material for liquid crystal display device of the invention, can enumerate for example, using high speed point
Dissipate machine (ホ モ デ ィ ス パ ー), mulser (ホ モ ミ キ サ ー), universal mixer, planetary-type mixer, kneader, 3 rollers
Deng mixing machine by the addition such as curable resin, optical free radical polymerization initiator and silane coupling agent for being added as needed
The method etc. of agent mixing.
By cooperating electrically conductive microparticle in sealing material for liquid crystal display device of the invention, conductive material up and down can be manufactured
Material.Such conductive material up and down containing sealing material for liquid crystal display device and electrically conductive microparticle of the invention also belongs to this hair
It is one of bright.
As the electrically conductive microparticle, metal ball can be used, form the tree of conductive metal layer on the surface of resin particle
Rouge particle etc..Especially, surface forms the resin particle of conductive metal layer, passes through the excellent elasticity of resin particle, Neng Gou
It is conductively connected in the case where not damaging transparent panel etc., it is advantageous to.
Use liquid crystal display made of sealing material for liquid crystal display device of the invention or conductive material up and down of the invention
Element also belongs to one of present invention.
The method of the liquid crystal display element of the invention as manufacture is, it is preferable to use liquid crystal drop processing method.It can specifically enumerate
Out such as the method included the following process: the glass substrate or polyethylene terephthalate of the electrode having ito thin film
1 upper sealing material for liquid crystal display device of the invention by the coating such as silk-screen printing, distributor in 2 pieces of plates of substrate etc.
Deng the process for forming the seal pattern of frame-shaped；It will in the state that sealing material for liquid crystal display device of the invention etc. is uncured
The tiny droplets of liquid crystal are added dropwise in the frame for the seal pattern for being applied to substrate, under vacuum with the process of another substrates while stacking；To this
The light of the seal pattern partial illumination ultraviolet light of the sealing material for liquid crystal display device of invention etc. etc. keeps sealant temporarily cured
Process；And the process etc. of formal solidification is carried out to the sealant heating temporarily having cured.
Invention effect
By means of the invention it is possible to provide photo-curable and the excellent sealing material for liquid crystal display device of low liquid crystal pollution.
In addition, by means of the invention it is possible to providing using upper and lower conductive material and liquid crystal made of the sealing material for liquid crystal display device
Show element.
Detailed description of the invention
Fig. 1 is the ideograph for illustrating the evaluation method of light shielding part curability.
Specific embodiment
Embodiment is set forth below to be further elaborated with the present invention, but the present invention is not limited by these embodiments.
(synthesis of compound represented by formula (2))
Aluminium chloride 7.36g is added in methylene chloride 50mL, and then diphenyl sulfide 9.31g is added several times at 0 DEG C.
Next, being stirred at room temperature 2 hours in 0 DEG C of addition chloracetyl chloride 5.56g, then, adding aluminium chloride 7.33g and 4- at 0 DEG C
Methylvaleric acid chloride 7.06g, is stirred overnight.Obtained reaction mixture is injected in ice water, then by organic layer methylene chloride
It extracts.Use MgSO4The solution extracted is dry, concentration is purified residue by column chromatography, thus the powder as white
End obtains compound A represented by following formula (4).
Obtained compound A1.0g is added in acetone 30mL, then and then adds potassium carbonate 1.11g and salicylide
0.73g, stirred at reflux 3 hours.It adds water at room temperature into obtained reaction mixture, then adds hydrochloric acid and be acidified,
Obtain sediment.Obtained sediment is recycled by filtering, is dried, to obtain chemical combination represented by following formula (5)
Object B.
Obtained compound B-11 .0g is added in ethyl acetate 10mL, then so that add hydroxylammonium chloride 0.35g and
Pyridine 5mL, stirred at reflux 3 hours.Obtained reaction mixture is injected in water at room temperature, then by organic layer acetic acid second
Ester extracts.Use MgSO4The solution extracted is dry, concentration, thick product is purified with column chromatography, to obtain as light
Compound C represented by the following formula (6) of yellow solid.
Obtained compound C 300mg is added in ethyl acetate 14mL, then so that add chloroacetic chloride 78.5mg and
Triethylamine 111mg is stirred at room temperature 3 hours.Obtained reaction mixture is injected in water, then by organic layer acetic acid second
Ester extracts.The solution of extraction is concentrated, thick product is purified with column chromatography, thus obtains chemical combination represented by the formula (2)
Object.
Furthermore the structure of compound represented by obtained formula (2) passes through1H-NMR、13C-NMR and FT-IR analysis comes true
Recognize.
(synthesis of compound represented by formula (3))
In addition to using positive caprylyl chloride 8.53g come other than replacing 4- methylvaleric acid chloride 7.06g, and described " (formula (2) is represented
Compound synthesis) " similarly, obtain compound represented by the formula (3).
Furthermore the structure of compound represented by obtained formula (3), passes through1H-NMR、13C-NMR and FT-IR analysis is true
Recognize.
(synthesis of compound represented by formula (7))
In addition to using fluorenes 8.3g come other than replacing diphenyl sulfide 9.31g, with the " (conjunction of compound represented by formula (2)
At) " similarly, obtain compound represented by following formula (7).
Furthermore the structure of compound represented by obtained formula (7) by1H-NMR、13C-NMR and FT-IR analysis comes true
Recognize.
(Examples 1 to 4, Comparative Examples 1 and 2)
According to match ratio recorded in table 1, by each materials'use planetary stirring machine (シ ン キ ー society system, " あ わ と り
Practice Taro ") mixing, it is mixed then and then using 3 rollers, modulates each liquid crystal display of Examples 1 to 4, Comparative Examples 1 and 2
Element sealant.
< evaluates >
Following evaluation is carried out to each sealing material for liquid crystal display device that embodiment and comparative example obtain.As a result such as 1 institute of table
Show.
(photo-curable)
Disperse spacer particle in 100 parts by weight of each sealing material for liquid crystal display device that embodiment and comparative example obtain
(ス ペ ー サ particulate, ponding chemical industry corporation system, " ミ Network ロ パ ー Le SI-H050 ") 1 parts by weight, and it is applied to glass
In glass plate.The glass plate of identical size is overlapped on plate after coating, next, using metal halide lamp with exposure 1000mJ/
cm2Light irradiation is carried out, light soundness test piece is made.No filter plate the case where and there is the case where 400nm or less filter plate to 2 figures
Case carries out light irradiation, makes 3 pieces of test films respectively.Using infrared spectroscopy device (BIORAD society system, " FTS3000 "), with 815~
800cm-1Peak area as the peak area from acryloyl group, measure the light irradiation front and back of the peak area from acryloyl group
Variable quantity evaluates photo-curable.Peak area from acryloyl group is with 845~820cm-1Peak area be used as referring to peak face
Derived from product.Light irradiation was denoted as " ◎ " from the situation that the peak area of acryloyl group reduces 90% or more later, after light is irradiated
Peak area from acryloyl group reduces 80% or more and is denoted as "○" the case where being less than 90%, comes from propylene after light is irradiated
The case where peak area reduction amount of acyl group is less than 80% is denoted as "×", in this way evaluation photo-curable.
Furthermore the variation measurement of the light irradiation front and back of the peak area from acryloyl group is averaged by what 3 pieces of test films obtained
Value.
(display performance of liquid crystal display element)
It is micro- to disperse spacer in 100 parts by weight of each sealing material for liquid crystal display device obtained in embodiment and comparative example
Grain (ponding chemical industry corporation system, " ミ Network ロ パ ー Le SI-H050 ") 1 parts by weight, alignment films and band after then being ground at 2 pieces
Have and is coated for the frame-shaped of 1mm using distributor on one of transparent electrode substrate with line width.
Connect it is lower in, the dropwise addition of the tiny droplets of liquid crystal (チ ッ ソ society system, " JC-5004LA ") is applied to transparent electrode
In the frame of the sealant of substrate in entire surface, it is bonded another substrate for having transparent electrode at once, sealant part is used
Metal halide lamp is 1000mJ/cm with exposure2Light irradiation is carried out, makes sealant cures, and then heat 1 hour at 120 DEG C, obtains
Liquid crystal display element.No filter plate the case where and there is the case where 400nm or less filter plate to carry out light irradiation to 2 patterns, respectively
Produce 3 pieces of liquid crystal display elements.
For obtained liquid crystal display element, after applying voltage 1000 hours at 60 DEG C near visual confirmation sealant
Liquid crystal pollution.
Liquid crystal pollution is to be judged according to the degree of the irregular colour of 3 pieces of liquid crystal display elements by following standard.
Will all liquid crystal display elements absolutely not irregular colour the case where be denoted as " ◎ ", will at least 1 piece of liquid crystal display element slightly
The case where irregular colour, is denoted as "○", at least will have the case where a little irregular colour to be denoted as " △ " by 1 piece of liquid crystal display element, near
Few 1 piece of more serious situation of liquid crystal display element irregular colour is denoted as "×", evaluates the display performance of liquid crystal display element.
Furthermore it is evaluated as " ◎ ", the liquid crystal display element of "○" is the absolutely not level of problem on practical.
(light shielding part curability)
The light shielding part curability of each sealing material for liquid crystal display device obtained in embodiment and comparative example, is by following
Measure the conversion ratio of the acryloyl group of each measuring point like that evaluate.Fig. 1 is the mould for illustrating the evaluation method of light shielding part curability
Formula figure.
Prepare the one side of the glass (length 30mm, width 30mm, thickness 0.7mm) of コ ー ニ Application グ society out respectively
The substrate 2 (Fig. 1 (a)) that chromium is deposited on the substrate 1 and entire one side of chromium is deposited in half.In vapor deposition that surface side of chromium of substrate 1
5 μm of 1 weight of polymeric beads is added in each sealing material for liquid crystal display device that central portion is coated on embodiment and comparative example obtains
Each that surface side of constituent of coating of substrate 1 and that surface side of the vapor deposition chromium of substrate 2 are overlapped, then by each 20mg of composition for measuring %
Sufficiently pressing (Fig. 1 (b)).
Next, penetrated from 1 surface side of substrate using metal halide lamp from 400nm or less filter plate on the substrate of coincidence
State, irradiation 100mW/cm2Ultraviolet light 30 seconds.Substrate 1,2 is peeled off using cutter.Next, using micro- IR method to ultraviolet
Line direct irradiation portion (position A), from the point (position B) of the limit to light shielding part lateral deviation from 25 μm in ultraviolet light direct irradiation portion and
Sealant (Fig. 1 (c)) from the marginal point (position C) to light shielding part lateral deviation from 50 μm in ultraviolet light direct irradiation portion, uses
Infrared spectroscopy device (BIORAD society system, " FTS3000 ") confirms the peak from acryloyl group.With 815~800cm-1Peak area
As the peak area from acryloyl group, by 845~820cm-1Peak area be used as referring to peak area, pass through following formula and calculate third
The conversion ratio of enoyl-.By the situation that the conversion ratio of acryloyl group is 75% or more be denoted as " ◎ ", will be 60% more than and less than
75% the case where be denoted as "○", by 50% more than and less than 60% the case where be denoted as " △ ", will be less than 50% the case where be denoted as
"×" evaluates light shielding part curability.
The conversion ratio (%)=100 of acryloyl group × (1- (peak area/purple from acryloyl group after ultraviolet light irradiation
Outside line irradiation after referring to peak area)/(when peak area/ultraviolet light from acryloyl group when ultraviolet light does not irradiate does not irradiate
Reference peak area))
Industry utilizability
By means of the invention it is possible to provide photo-curable and the excellent sealing material for liquid crystal display device of low liquid crystal pollution.
In addition, by means of the invention it is possible to providing using upper and lower conductive material and liquid crystal made of the sealing material for liquid crystal display device
Show element.
Symbol description
The substrate of chromium is deposited in the half of 1 one side
11 chromium steam plating parts
The substrate of chromium is deposited in 2 entire one sides
21 chromium steam plating parts
3 position A
4 position B
5 position C.
Claims (5)
1. a kind of sealing material for liquid crystal display device, which is characterized in that containing curable resin and optical free radical polymerization initiator,
The optical free radical polymerization initiator contains following formula (1) compound represented,
In formula (1), R1Indicate hydrogen atom, the alkyl or alicyclic ring that carbon atom number is 1 or more and 10 straight-chains or branched below
Formula alkyl, R2Indicate heteroaryl, R3Expression carbon atom number is 1 or more and 6 alkyl or aryl below.
2. sealing material for liquid crystal display device as described in claim 1, which is characterized in that optical free radical polymerization initiator contains
Following formula (2) compound represented as compound represented by formula (1),
3. sealing material for liquid crystal display device as claimed in claim 1 or 2, which is characterized in that compound represented by formula (1)
Content relative to 100 parts by weight of curable resin be 0.1 parts by weight more than and 5 parts by weight below.
4. a kind of conductive material up and down, which is characterized in that contain 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 element, which is characterized in that used described in claim 1,2 or 3 used for liquid crystal display element close
Seal agent or conductive material up and down as claimed in claim 4.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2017110842 | 2017-06-05 | ||
| JP2017-110842 | 2017-06-05 | ||
| PCT/JP2018/021630 WO2018225754A1 (en) | 2017-06-05 | 2018-06-05 | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110383159A true CN110383159A (en) | 2019-10-25 |
Family
ID=64566732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201880016547.7A Pending CN110383159A (en) | 2017-06-05 | 2018-06-05 | Sealing material for liquid crystal display device, upper and lower conductive material and liquid crystal display element |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPWO2018225754A1 (en) |
| KR (1) | KR20200016199A (en) |
| CN (1) | CN110383159A (en) |
| TW (1) | TW201902947A (en) |
| WO (1) | WO2018225754A1 (en) |
Family Cites Families (7)
| 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 |
| KR101736126B1 (en) | 2010-06-28 | 2017-05-16 | 가부시키가이샤 아데카 | Curable resin composition |
| JP2012173488A (en) * | 2011-02-21 | 2012-09-10 | Sekisui Chem Co Ltd | Sealing agent for liquid crystal dropping method, and manufacturing method of liquid crystal display |
| EP3044208B1 (en) * | 2013-09-10 | 2021-12-22 | Basf Se | Oxime ester photoinitiators |
| DE102016121484B3 (en) * | 2016-11-09 | 2017-12-28 | Tesat-Spacecom Gmbh & Co. Kg | Device for a transmitting and receiving unit of a communication device and spacecraft, comprising such a device |
| JP6338745B1 (en) * | 2016-12-27 | 2018-06-06 | 日本化薬株式会社 | Photocurable resin composition and sealant for electronic parts |
-
2018
- 2018-06-05 CN CN201880016547.7A patent/CN110383159A/en active Pending
- 2018-06-05 TW TW107119398A patent/TW201902947A/en unknown
- 2018-06-05 KR KR1020197029581A patent/KR20200016199A/en unknown
- 2018-06-05 WO PCT/JP2018/021630 patent/WO2018225754A1/en active Application Filing
- 2018-06-05 JP JP2019523925A patent/JPWO2018225754A1/en active Pending
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| Publication number | Publication date |
|---|---|
| KR20200016199A (en) | 2020-02-14 |
| TW201902947A (en) | 2019-01-16 |
| JPWO2018225754A1 (en) | 2020-04-23 |
| WO2018225754A1 (en) | 2018-12-13 |
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Application publication date: 20191025 |