TWI504667B - A hardened resin composition, a sealant for a liquid crystal display element, and a liquid crystal display element - Google Patents
A hardened resin composition, a sealant for a liquid crystal display element, and a liquid crystal display element Download PDFInfo
- Publication number
- TWI504667B TWI504667B TW102143740A TW102143740A TWI504667B TW I504667 B TWI504667 B TW I504667B TW 102143740 A TW102143740 A TW 102143740A TW 102143740 A TW102143740 A TW 102143740A TW I504667 B TWI504667 B TW I504667B
- Authority
- TW
- Taiwan
- Prior art keywords
- liquid crystal
- weight
- crystal display
- curable resin
- resin composition
- Prior art date
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- 239000004973 liquid crystal related substance Substances 0.000 title claims description 324
- 239000011342 resin composition Substances 0.000 title claims description 175
- 239000000565 sealant Substances 0.000 title claims description 103
- 239000000758 substrate Substances 0.000 claims description 97
- 238000000034 method Methods 0.000 claims description 55
- 239000002245 particle Substances 0.000 claims description 28
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 238000001914 filtration Methods 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 7
- 229920005989 resin Polymers 0.000 description 93
- 239000011347 resin Substances 0.000 description 93
- 239000003822 epoxy resin Substances 0.000 description 78
- 229920000647 polyepoxide Polymers 0.000 description 78
- 239000007870 radical polymerization initiator Substances 0.000 description 64
- 150000001875 compounds Chemical class 0.000 description 59
- 238000007789 sealing Methods 0.000 description 58
- 238000006243 chemical reaction Methods 0.000 description 55
- 239000003795 chemical substances by application Substances 0.000 description 55
- 125000000524 functional group Chemical group 0.000 description 54
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 41
- 230000009477 glass transition Effects 0.000 description 40
- 239000010419 fine particle Substances 0.000 description 39
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 38
- -1 for example Chemical group 0.000 description 36
- 239000011521 glass Substances 0.000 description 33
- 239000003505 polymerization initiator Substances 0.000 description 33
- 239000007788 liquid Substances 0.000 description 32
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 31
- 150000003254 radicals Chemical class 0.000 description 28
- 239000000203 mixture Substances 0.000 description 27
- 239000000047 product Substances 0.000 description 26
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 24
- 210000004027 cell Anatomy 0.000 description 23
- 230000000052 comparative effect Effects 0.000 description 23
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 22
- 239000000463 material Substances 0.000 description 22
- 238000003756 stirring Methods 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 238000011156 evaluation Methods 0.000 description 21
- 238000012360 testing method Methods 0.000 description 21
- 238000001723 curing Methods 0.000 description 20
- 238000011109 contamination Methods 0.000 description 18
- 239000012948 isocyanate Substances 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 14
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- 125000003700 epoxy group Chemical group 0.000 description 14
- 239000000178 monomer Substances 0.000 description 14
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 13
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- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 9
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 9
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 9
- 239000010453 quartz Substances 0.000 description 9
- 125000006850 spacer group Chemical group 0.000 description 9
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- 235000012211 aluminium silicate Nutrition 0.000 description 8
- 239000002585 base Substances 0.000 description 8
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- 239000007809 chemical reaction catalyst Substances 0.000 description 8
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- 229920001187 thermosetting polymer Polymers 0.000 description 8
- MFAWEYJGIGIYFH-UHFFFAOYSA-N 2-[4-(trimethoxymethyl)dodecoxymethyl]oxirane Chemical compound C(C1CO1)OCCCC(C(OC)(OC)OC)CCCCCCCC MFAWEYJGIGIYFH-UHFFFAOYSA-N 0.000 description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 238000000862 absorption spectrum Methods 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 230000001976 improved effect Effects 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229930185605 Bisphenol Natural products 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 description 6
- XJDCHDFUMGSEHD-UHFFFAOYSA-N NCCCC(C(OC)(OC)OC)CCCCCCCC Chemical compound NCCCC(C(OC)(OC)OC)CCCCCCCC XJDCHDFUMGSEHD-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
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- 150000004292 cyclic ethers Chemical group 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
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- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 6
- 230000000717 retained effect Effects 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 5
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 5
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 5
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 description 4
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- 239000003708 ampul Substances 0.000 description 4
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
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- 238000004566 IR spectroscopy Methods 0.000 description 3
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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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/064—Polymers containing more than one epoxy group per molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/34—Epoxy compounds containing three or more epoxy groups obtained by epoxidation of an unsaturated polymer
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L63/10—Epoxy resins modified by unsaturated compounds
-
- 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Liquid Crystal (AREA)
- Sealing Material Composition (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003159905 | 2003-06-04 | ||
| JP2003159909 | 2003-06-04 | ||
| JP2003159906 | 2003-06-04 | ||
| JP2003162774A JP2004361854A (ja) | 2003-06-06 | 2003-06-06 | 液晶表示素子 |
| JP2003165410 | 2003-06-10 | ||
| JP2003270397 | 2003-07-02 | ||
| JP2003279299 | 2003-07-24 | ||
| JP2003284115 | 2003-07-31 | ||
| JP2003394618A JP2005060651A (ja) | 2003-07-31 | 2003-11-25 | 硬化性樹脂組成物、液晶表示素子用シール剤、液晶表示素子用封口剤、液晶表示素子用上下導通材料及び液晶表示素子 |
| JP2003394615A JP4022194B2 (ja) | 2003-06-04 | 2003-11-25 | 液晶表示素子用硬化性樹脂組成物、液晶表示素子用シール剤、液晶表示素子用封口剤、液晶表示素子用上下導通材料、及び、液晶表示装置 |
| JP2003394619A JP2005025156A (ja) | 2003-06-10 | 2003-11-25 | 液晶表示素子用硬化性樹脂組成物、液晶表示素子用シール剤、液晶表示素子用封口剤、液晶表示素子用上下導通材料及び液晶表示素子 |
| JP2003394616A JP4532883B2 (ja) | 2003-06-04 | 2003-11-25 | 光硬化性樹脂組成物、液晶表示素子用シール剤、液晶表示素子用封口剤、液晶表示素子用上下導通材料及び液晶表示装置 |
| JP2003394617A JP2005015758A (ja) | 2003-06-04 | 2003-11-25 | 硬化性樹脂組成物、液晶表示素子用シール剤、液晶表示素子用封口剤、液晶表示素子用上下導通材料及び液晶表示素子 |
| JP2003394614A JP2005054164A (ja) | 2003-07-24 | 2003-11-25 | 光熱硬化性樹脂組成物、液晶表示素子用シール剤、液晶表示素子用封口剤、液晶表示素子用上下導通材料及び液晶表示装置 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201414786A TW201414786A (zh) | 2014-04-16 |
| TWI504667B true TWI504667B (zh) | 2015-10-21 |
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Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW099125906A TWI509015B (zh) | 2003-06-04 | 2004-06-04 | A hardened resin composition, a sealant for a liquid crystal display element, and a liquid crystal display element |
| TW102143740A TWI504667B (zh) | 2003-06-04 | 2004-06-04 | A hardened resin composition, a sealant for a liquid crystal display element, and a liquid crystal display element |
| TW093116052A TW200508314A (en) | 2003-06-04 | 2004-06-04 | A liquid crystal display device and curing resin composition, sealing material for the same |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW099125906A TWI509015B (zh) | 2003-06-04 | 2004-06-04 | A hardened resin composition, a sealant for a liquid crystal display element, and a liquid crystal display element |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
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| TW093116052A TW200508314A (en) | 2003-06-04 | 2004-06-04 | A liquid crystal display device and curing resin composition, sealing material for the same |
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| US (2) | US20090093562A1 (enExample) |
| EP (1) | EP1640396A1 (enExample) |
| KR (3) | KR100935774B1 (enExample) |
| TW (3) | TWI509015B (enExample) |
| WO (1) | WO2004108790A1 (enExample) |
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| US7588931B2 (en) | 2004-11-04 | 2009-09-15 | E. I. Du Pont De Nemours And Company | High arachidonic acid producing strains of Yarrowia lipolytica |
| WO2006120998A1 (ja) * | 2005-05-09 | 2006-11-16 | Sekisui Chemical Co., Ltd. | 液晶滴下工法用シール剤、上下導通材料及び液晶表示素子 |
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| CN109196413B (zh) * | 2016-12-27 | 2021-03-16 | 积水化学工业株式会社 | 液晶显示元件用密封剂、上下导通材料和液晶显示元件 |
| WO2019221027A1 (ja) * | 2018-05-17 | 2019-11-21 | 積水化学工業株式会社 | 液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子 |
| JP2020029477A (ja) * | 2018-08-20 | 2020-02-27 | Dic株式会社 | エポキシ（メタ）アクリレート樹脂、エポキシ（メタ）アクリレート樹脂組成物、硬化性樹脂組成物、硬化物及び物品 |
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- 2004-06-04 WO PCT/JP2004/007811 patent/WO2004108790A1/ja not_active Ceased
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Also Published As
| Publication number | Publication date |
|---|---|
| US20090093562A1 (en) | 2009-04-09 |
| TW200508314A (en) | 2005-03-01 |
| KR100935774B1 (ko) | 2010-01-06 |
| WO2004108790A1 (ja) | 2004-12-16 |
| KR20090091814A (ko) | 2009-08-28 |
| EP1640396A1 (en) | 2006-03-29 |
| KR20090089912A (ko) | 2009-08-24 |
| TW201414786A (zh) | 2014-04-16 |
| US20090134358A1 (en) | 2009-05-28 |
| KR20060017628A (ko) | 2006-02-24 |
| TWI344975B (enExample) | 2011-07-11 |
| KR101180600B1 (ko) | 2012-09-06 |
| TW201100489A (en) | 2011-01-01 |
| TWI509015B (zh) | 2015-11-21 |
| KR100952263B1 (ko) | 2010-04-09 |
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