JPS63251422A - Photocurable resin composition for sealing - Google Patents
Photocurable resin composition for sealingInfo
- Publication number
- JPS63251422A JPS63251422A JP8628487A JP8628487A JPS63251422A JP S63251422 A JPS63251422 A JP S63251422A JP 8628487 A JP8628487 A JP 8628487A JP 8628487 A JP8628487 A JP 8628487A JP S63251422 A JPS63251422 A JP S63251422A
- Authority
- JP
- Japan
- Prior art keywords
- component
- resin composition
- liquid crystal
- sealing
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 21
- 238000007789 sealing Methods 0.000 title claims description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 239000003822 epoxy resin Substances 0.000 claims abstract description 18
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 18
- 239000004593 Epoxy Substances 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 17
- 229920005989 resin Polymers 0.000 claims abstract description 13
- 239000011347 resin Substances 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 238000010538 cationic polymerization reaction Methods 0.000 claims abstract description 6
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 5
- 239000000539 dimer Substances 0.000 claims abstract description 4
- 230000000977 initiatory effect Effects 0.000 claims abstract description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 8
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 36
- 210000002858 crystal cell Anatomy 0.000 abstract description 20
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 238000002156 mixing Methods 0.000 abstract description 4
- 125000004185 ester group Chemical group 0.000 abstract 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000565 sealant Substances 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- -1 phosphorus ethers Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 238000011056 performance test Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 239000005297 pyrex Substances 0.000 description 3
- 238000007650 screen-printing Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000004010 onium ions Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- DXEHULHXWHEJJD-UHFFFAOYSA-N 2-[(4-butylphenoxy)methyl]oxirane Chemical compound C1=CC(CCCC)=CC=C1OCC1OC1 DXEHULHXWHEJJD-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- HNUKTDKISXPDPA-UHFFFAOYSA-N 2-oxopropyl Chemical compound [CH2]C(C)=O HNUKTDKISXPDPA-UHFFFAOYSA-N 0.000 description 1
- RCXHRHWRRACBTK-UHFFFAOYSA-N 3-(oxiran-2-ylmethoxy)propane-1,2-diol Chemical compound OCC(O)COCC1CO1 RCXHRHWRRACBTK-UHFFFAOYSA-N 0.000 description 1
- XAYDWGMOPRHLEP-UHFFFAOYSA-N 6-ethenyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCCC2OC21C=C XAYDWGMOPRHLEP-UHFFFAOYSA-N 0.000 description 1
- GJEZBVHHZQAEDB-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hexane Chemical compound C1CCC2OC21 GJEZBVHHZQAEDB-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 241000238557 Decapoda Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229910052777 Praseodymium Inorganic materials 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052768 actinide Inorganic materials 0.000 description 1
- 150000001255 actinides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000005251 aryl acyl group Chemical group 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Polymers C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 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 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Liquid Crystal (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
Abstract
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は、封着用光硬化性樹脂組成物に関する。[Detailed description of the invention] (Industrial application field) The present invention relates to a photocurable resin composition for sealing.
より詳しくは、本発明は液晶セルの製造時に基板を貼り
合わせ若しくは封止するための接着性、封止性および液
晶適性に優れた封着用光硬化性樹脂組成物に関する。More specifically, the present invention relates to a photocurable resin composition for sealing that has excellent adhesive properties, sealing properties, and liquid crystal suitability for bonding or sealing substrates during the production of liquid crystal cells.
（従来の技術）
従来、２枚のガラスまたはプラスチック製基板間に液晶
を封止した液晶セルが表示装置等に多用されている。こ
の液晶セルは通常２枚の基板を接着し、かつ液晶を良好
に封止し得る封着剤が用いられる。(Prior Art) Conventionally, liquid crystal cells in which liquid crystal is sealed between two glass or plastic substrates have been widely used in display devices and the like. This liquid crystal cell usually uses a sealing agent that can bond two substrates together and seal the liquid crystal well.
従来、これらの封着剤と１．ては、ｌ液または２液型の
エポキシ余熱硬化性樹１１ｉ組成物が用いられてきた。Conventionally, these sealants and 1. For this purpose, one-part or two-part epoxy heat-curable resin 11i compositions have been used.
しかし、封着剤の組成物類が液晶に溶出するために液晶
配向の異常、液晶の劣化が多々発生した。また高温で長
時間の硬化工程を必要とするため、生産性の面で大きな
問題があった。また液晶の劣化を防ぐために高温加熱が
できず、封着剤の硬化には低温で長時間を要することに
なり、このため封着１剤組成物の液晶中への溶出による
配向異常、硬化不良などが発生して品質、品質管理、生
産面でやはり大きな問題となっていた。However, because the sealant compositions were eluted into the liquid crystal, abnormalities in liquid crystal alignment and deterioration of the liquid crystal frequently occurred. Furthermore, since it requires a curing process at high temperature and for a long time, there is a big problem in terms of productivity. In addition, high-temperature heating is not possible to prevent liquid crystal deterioration, and curing of the sealant requires a long time at low temperature, resulting in abnormal orientation and poor curing due to elution of the sealing agent composition into the liquid crystal. This caused major problems in terms of quality, quality control, and production.
（発明が解決しようとする問題点）
上記問題点を解決するために、光硬化性の封着剤が種々
検討されている。光硬化性の封着剤は通常エポキシ樹脂
と光重合開始剤との組合せが考えられる。しかしながら
、この組合せでは接着力が不足し、液晶セルに外圧がか
かると樹脂封着部が剥離し、液晶が漏出する。また硬化
物のガラス転移温度（Ｔｇ）が低くバリヤー性が不足し
、耐冷熱ザイクル性が低い。(Problems to be Solved by the Invention) In order to solve the above problems, various photocurable sealants have been studied. The photocurable sealant is usually a combination of an epoxy resin and a photopolymerization initiator. However, this combination lacks adhesive strength, and when external pressure is applied to the liquid crystal cell, the resin sealing part peels off and liquid crystal leaks. In addition, the cured product has a low glass transition temperature (Tg), is insufficient in barrier properties, and has low cold and heat cycle resistance.
特開昭６０−２１７２３１号公報には上記欠点を解消す
るために、エポキシ樹脂と光重合開始剤の系にエポキシ
化ブタジェンポリマーを配合するが、硬化物中に残留す
る溶出性の低分子物質のために液晶を汚染する恐れがあ
る。In order to solve the above-mentioned drawbacks, JP-A No. 60-217231 incorporates an epoxidized butadiene polymer into the system of epoxy resin and photopolymerization initiator; There is a risk of contaminating the liquid crystal.
特開昭６０−２１３２１７号公報には上記特開昭６０−
２１７２３１号公報の組成物中に重合可能な置換基を有
する増感剤を配合する技術が開示されている。しかしな
がら、得られた液晶セルの水分、熱等に対する化学的・
物理的な安定性が不十分である。JP-A-60-213217 has the above-mentioned JP-A-60-213217.
No. 217231 discloses a technique of incorporating a sensitizer having a polymerizable substituent into a composition. However, the chemical resistance of the obtained liquid crystal cell to moisture, heat, etc.
Physical stability is insufficient.
特開昭６２１７７２９号公報にはエポキシ樹脂、光重合
開始剤および特定のポリオール類を含有する封止用の光
硬化性樹脂組成物が開示されている。しかしながら、ポ
リオール類の添加は反応性を低下し、条里の照射光量を
必要とする。JP-A-6217729 discloses a photocurable resin composition for sealing containing an epoxy resin, a photopolymerization initiator, and specific polyols. However, the addition of polyols reduces the reactivity and requires a larger amount of irradiation light.
（問題点を解決するための手段）
本発明は前述した従来の光硬化型の封着剤の諸欠点を解
消したもので、液晶セルの水分・熱等に対する化学的・
物理的安定性が優れ、高品質の液晶セルを少量の照射光
量で硬化し、従来の製造工程よりも簡略に、しかも短時
間に製造できる封着＝３−
用光硬化性樹脂組成物を提供することにある。(Means for Solving the Problems) The present invention eliminates the various drawbacks of the conventional photocurable sealant described above, and has chemical resistance against moisture, heat, etc. of liquid crystal cells.
Provides a photocurable resin composition for sealing = 3- that has excellent physical stability, cures high-quality liquid crystal cells with a small amount of irradiation light, and can be manufactured more simply and in a shorter time than conventional manufacturing processes. It's about doing.
即ち、本発明は（Ａ） 主鎖中にエステル結合を有し
、かつ分子末端にグリシジルエーテル基を少なくとも１
個有する樹脂、（Ｂ）（Ａ）成分以外のエポキシ化合物
、および（Ｃ） 光照射によりカチ 。That is, the present invention provides (A) having an ester bond in the main chain and at least one glycidyl ether group at the end of the molecule.
(B) an epoxy compound other than the component (A), and (C) a chemical compound that is irradiated with light.
オン重合開始能を有する化合物を含有する封着用光硬化
性樹脂組成物を提供する。A photocurable resin composition for sealing containing a compound having on-polymerization initiating ability is provided.
（作用）
本発明では従来のエポキシ化合物および光重合開始剤の
系に、ポリエステル結合を有するエポキシ樹脂を導入す
ることにより、ポリエステル結合による可撓性が硬化樹
脂に耐久性、化学的および物理的な安定性を付与するも
のと考えられる。(Function) In the present invention, by introducing an epoxy resin having a polyester bond into the conventional epoxy compound and photopolymerization initiator system, the flexibility due to the polyester bond can be added to the cured resin to improve durability, chemical and physical properties. It is thought that it provides stability.
本発明で用いられる（Ａ）成分の樹脂はエステル結合を
主鎖中に有し、分子末端にグリシジルエーテル基を１分
子中に少なくとも平均１個以上有する樹脂が用いられる
。好適な樹脂の例としては二塩基酸１モルとエポキシ樹
脂２モルとを反応させて得られる樹脂で例えばダイマー
酸変性エポキシ樹脂、末端カルボン酸のポリエステル樹
脂１モルに対してエポキシ樹脂２モルを反応させて得ら
れるポリエステル変性エポキシ樹脂が挙げられる。The resin component (A) used in the present invention has an ester bond in its main chain and an average of at least one glycidyl ether group per molecule at the terminal end of the molecule. Examples of suitable resins include resins obtained by reacting 1 mole of dibasic acid with 2 moles of epoxy resin, such as dimer acid-modified epoxy resin, and 2 moles of epoxy resin reacted with 1 mole of terminal carboxylic acid polyester resin. Examples include polyester-modified epoxy resins obtained by
このような樹脂の製法は公知であり、特に説明は要しな
い。The method for producing such a resin is well known and does not require any particular explanation.
本発明で用いられる上記（Ａ）成分以外のエポキシ樹脂
（Ｂ）成分は、より具体的には脂環式エポキシ化合物、
芳香族エポキシ化合物、さらに脂肪族エポキシ化合物ま
たはそれらの混合物が挙げられる。脂環式エポキシ樹脂
は少なくとも１個の脂環を有する多価アルコールのポリ
グリシジルエーテル又はシクロヘキセンまたはシクロペ
ンテン環含有化合物を過酸化水素、過酸等の適当な酸化
剤でエポキシ化することによって得られるシクロヘキセ
ンオキサイド又はシクロペンテンオキザイド含有化合物
である。多価アルコールのポリグリシジルエーテルの代
表例としては、水素添加ビスフェノールＡまたはそのア
ルキレンオキサイド付加体とエビクロロヒドリンとの反
応によって製造されるグリシジルエーテルが挙げられる
。シクロヘキセンオキサイド又はノクロペンテンオキザ
イド含何代合物の代表例としては、下記の式で表わされ
るものが挙げられる。More specifically, the epoxy resin (B) component other than the above-mentioned (A) component used in the present invention is an alicyclic epoxy compound,
Mention may be made of aromatic epoxy compounds as well as aliphatic epoxy compounds or mixtures thereof. Alicyclic epoxy resin is a polyglycidyl ether of a polyhydric alcohol having at least one alicyclic ring, or cyclohexene obtained by epoxidizing a compound containing a cyclohexene or cyclopentene ring with an appropriate oxidizing agent such as hydrogen peroxide or peracid. It is a compound containing oxide or cyclopentene oxide. A typical example of polyglycidyl ether of polyhydric alcohol is glycidyl ether produced by reacting hydrogenated bisphenol A or its alkylene oxide adduct with shrimp chlorohydrin. Representative examples of compounds containing cyclohexene oxide or noclopentene oxide include those represented by the following formula.
Ｏ
芳香族エボギシ化合物としてはビスフェノールＡ型エポ
キシ樹脂、ヒスフェノールＦ型エポキシ樹脂、ノボラッ
ク型エボキノ樹脂、ハロゲン化ビスフェノールＡ型エポ
キシ樹脂等が挙げられる。O Examples of aromatic epoxy compounds include bisphenol A type epoxy resin, hisphenol F type epoxy resin, novolak type evoquino resin, and halogenated bisphenol A type epoxy resin.
さらに脂肪族エポキシ化合物として特に好ましいものは
脂肪族多価アルコールまたはそのアルキレンオキサイド
イ」加物のポリグリシジルエーテルがあり、この代表例
としては、１，４−ブタンジオールのジグリシジルエー
テル、１．６−ヘキザンジオールのジグリシジルエーテ
ル、グリセリンのトリグリンンルエーテル、）・リメヂ
ロールプロパンのトリクリノジルエーテル、ポリエチレ
ングリコールのジグリシジルエーテル、ポリプロピレン
グリコールのジグリシジルエーテル、エヂレン−７＝
グリコール、プロピレングリコール、グリセリン等の脂
肪族多価アルコールに１種または２種以上のアルキレン
オキサイド（エチレンオキザイド、プロピレンオキサイ
ド）を付加することにより得られるポリエーテルポリオ
ールのポリグリシジルエーテルが挙げられる。加えて、
脂肪族エポキシ化合物にはモノアルコールのグリンンル
エーテルも包含される。そのようなものの例としてはブ
チルグリシジルエーテル、アリルグリシジルエーテル、
２−エヂルヘキシルグリシジルエーテル、フェニルグリ
ンジルエーテル、ｐ−ブチルフェニルグリシジルエーテ
ル、グリセリングリシジルエーテル、ネオペンチルグリ
コールジグリシジルエーテルなどが挙げられる。Particularly preferable aliphatic epoxy compounds are polyglycidyl ethers of aliphatic polyhydric alcohols or their alkylene oxide additions; typical examples include diglycidyl ether of 1,4-butanediol, 1.6 - diglycidyl ether of hexanediol, triglycidyl ether of glycerin, triclinodyl ether of rimedylolpropane, diglycidyl ether of polyethylene glycol, diglycidyl ether of polypropylene glycol, ethylene-7= glycol, propylene glycol and polyglycidyl ethers of polyether polyols obtained by adding one or more alkylene oxides (ethylene oxide, propylene oxide) to aliphatic polyhydric alcohols such as glycerin. In addition,
Aliphatic epoxy compounds also include monoalcoholic phosphorus ethers. Examples of such are butyl glycidyl ether, allyl glycidyl ether,
Examples include 2-edylhexyl glycidyl ether, phenyl glycidyl ether, p-butylphenyl glycidyl ether, glycerin glycidyl ether, neopentyl glycol diglycidyl ether, and the like.
本発明に用いられる光照射によりカチオン重合開始能を
有する化合物としては、いかなるものを用いてもよく、
特に活性エネルギー線の照射によりカチオン重合開始能
を有する物質を放出するオニウム化合物が好適である。Any compound having the ability to initiate cationic polymerization upon irradiation with light may be used in the present invention.
Particularly suitable are onium compounds that release a substance having the ability to initiate cationic polymerization upon irradiation with active energy rays.
この化合物は具体的には、
＝８−
によって一層明確に定義することができる。式中、Ｒは
１価の芳香族有機基、Ｒ１はアルギル基、シクロアルキ
ル基および置換アルキル苓の中から選ばれた１価の脂肪
族有機基、Ｒ′は脂肪族基および芳香族基の中から選ば
れた複素環式または融合環式構造の多価有機基、Ｘはジ
アゾニウム、ハロゲン、窒素、ヒ素、アンチモン、ビス
マス、イオウ、セレンおよびテルルの中から選ばれた元
素、Ｍは金属または半金属、モしてＱはハロゲン原子で
ある。また、ａはＯ〜３の整数、ｂは０〜２の整数、か
つＣは０〜Ｉの整数であって、和（ａ＋ｂ＋ｃ）はＸの
原子価すなわち３に等しく、ｄは（ｅ−１’）に等しく
、ｆはＭの原子価に等しい２〜７の整数であり、そして
ｅはｒより大きい５までの整数である。This compound can specifically be more clearly defined by =8-. In the formula, R is a monovalent aromatic organic group, R1 is a monovalent aliphatic organic group selected from an argyl group, a cycloalkyl group, and a substituted alkyl group, and R' is an aliphatic group and an aromatic group. a polyvalent organic group with a heterocyclic or fused ring structure selected from among; X is an element selected from diazonium, halogen, nitrogen, arsenic, antimony, bismuth, sulfur, selenium and tellurium; M is a metal or In semimetals, Q is a halogen atom. Further, a is an integer from 0 to 3, b is an integer from 0 to 2, and C is an integer from 0 to I, the sum (a+b+c) is equal to the valence of X, that is, 3, and d is (e-1 '), f is an integer from 2 to 7 equal to the valence of M, and e is an integer from 5 to 5 that is greater than r.
Ｒによって表わされる基としては、例えば、Ｃ４〜１５
芳香族炭化水素た七えばフェニル基、トリル基、ナフチ
ル基、アントリル基、および１〜４個の１価の基（たと
えば０１〜。アルコキシ基、０１〜７アルキル基、ニト
ロ基、塩素原子、水酸基など）で置換されたぞれらの基
、アリールアシル基たとえばベンゾイル基、フェニルア
シル基など、並びに芳香族複素環式基たとえばピリジル
、フルフリル基などが挙げられる。Ｒ＋によって表４つ
される基としては、たとえば、０１〜６アルキル基およ
び置換アルキル基（たとえば−Ｃ２Ｈ４０ＣＨ３、−Ｃ
Ｈ２ＣＯＯＣ２Ｈ５、ＣＨ２ＣＯＣＨ３など）が挙げら
れる。Ｒ２によって表わされる基としては、たとえば式
などで表わされる基が挙げられる。式（１）中の［ＭＱ
ｅｌ ”によって表わされる陰イオンとしては、たと
えばＢＰ、−１ＰＦ４−１ＡＳＰ４−１Ｓｌ）ＦＯ−１
ＦｅＣ］４−１ＳｎＣＬ＋−１ＳｂＣ１４−１Ｂ ＋
ＣＩ５’−１ＡＩＦ６３−１ＣａＣ１４−１ＩｎＦ４−
１Ｔ＋Ｆｓ’−１ＺｒＦｏ−などが挙げられる。その場
合、Ｍは遷移金属たとえばＳｂ、 Ｆｅ、 Ｓｎ、 Ｂ
ｉ、ＡＩ。Examples of the group represented by R include C4-15
Aromatic hydrocarbons such as phenyl group, tolyl group, naphthyl group, anthryl group, and 1 to 4 monovalent groups (for example, 01 to 7 alkoxy groups, 01 to 7 alkyl groups, nitro groups, chlorine atoms, hydroxyl groups) etc.), arylacyl groups such as benzoyl group and phenyl acyl group, and aromatic heterocyclic groups such as pyridyl and furfuryl groups. Examples of groups represented by R+ include 01-6 alkyl groups and substituted alkyl groups (for example, -C2H40CH3, -C
H2COOC2H5, CH2COCH3, etc.). Examples of the group represented by R2 include groups represented by the following formulas. [MQ in formula (1)
Examples of the anion represented by "el" include BP, -1PF4-1ASP4-1Sl)FO-1
FeC]4-1SnCL+-1SbC14-1B+
CI5'-1AIF63-1CaC14-1InF4-
Examples include 1T+Fs'-1ZrFo-. In that case, M is a transition metal such as Sb, Fe, Sn, B
i, A.I.
Ｃａｓ Ｉ ｎ、 Ｔ ｉｓ Ｚｒ５Ｓ ０％ Ｖ−
、Ｃｒ、 Ｍｎ−、０８％希土類元素すなわちランタニ
ド（たとえばＣｅ、Ｐｒ、Ｎｄなど）およびアクチニド
（たとえばＴｈ。Cas In, T is Zr5S 0% V-
, Cr, Mn-, 08% rare earth elements i.e. lanthanides (e.g. Ce, Pr, Nd, etc.) and actinides (e.g. Th.
Ｐａ５Ｕ、Ｎｐなど） ｉｌ■２びに半金属たとえばＢ
、Ｐ。Pa5U, Np, etc.) il■2 and semimetals such as B
,P.
Ａｓなどであり得る。It can be As, etc.
光照射によりカヂオン重合開始能を有する化合物は」−
記オニウム化合物以外に特開昭５９−２１９３０７号に
記載のものを用いてもよい。A compound that has the ability to initiate cationic polymerization upon irradiation with light is
In addition to the above onium compounds, those described in JP-A-59-219307 may also be used.
本発明に係る樹脂組成物には、特に液晶セル周辺封着剤
として使用する場合にスクリーン印刷の作業性を向」ニ
させる目的で溶剤を使用してもよい。A solvent may be used in the resin composition according to the present invention for the purpose of improving the workability of screen printing, especially when used as a liquid crystal cell peripheral sealant.
この溶剤としては、ケトン系、エステル系、エーテル系
、脂肪族または芳香族炭化水素あるいは塩素系炭化水素
に属する各種溶剤類でスクリーンの乳剤をおかさないも
のが用いられる。溶剤の使用里は組成物中に含まれる重
電比が好ましくは２０重量％以内である。As this solvent, there are used various solvents belonging to the ketone, ester, ether, aliphatic or aromatic hydrocarbons, or chlorine hydrocarbons, which do not disturb the emulsion of the screen. The solvent to be used is preferably such that the heavy electric ratio contained in the composition is within 20% by weight.
また本発明に係る樹脂組成物には、物性の改質あるいは
用途などの必要に応じて種々の改質添加剤を配合するこ
とができる。例えば、液晶セル間に適当な間隔を保持さ
せるための粒状または針状のスペーザー；ンリカおよび
ガラスピーズなどのフィラー；接着性および耐湿性を向
上させるためのシリコーン系あるいはチタネート系、そ
の他のカップリング剤；スクリーン印刷性を付与するた
めのアエロジル、ベントンなどのチクソトロピック性付
与剤；フロラードなどのレベリング剤；水酸化アルミニ
ウム、水酸化バリウムなどの体質顔料；さらに石油樹脂
、ロジン、ナイロン、アクリル樹脂などの改良高分子物
質を配合することもできる。Furthermore, various modifying additives can be added to the resin composition according to the present invention as required for modifying physical properties or for purposes of use. For example, granular or acicular spacers to maintain proper spacing between liquid crystal cells; fillers such as liquid crystal and glass beads; silicone-based or titanate-based or other coupling agents to improve adhesion and moisture resistance. ; Thixotropic agents such as Aerosil and Bentone to impart screen printability; Leveling agents such as Florade; extender pigments such as aluminum hydroxide and barium hydroxide; Modified polymeric substances can also be incorporated.
本発明の組成物は、（Ａ）成分と（Ｂ）成分との配合比
率は（Ａ）成分力用０〜９０重量部、（Ｂ）成分が９０
〜ＩＯ重量部、好ましくは、（Ａ）成分が３０〜７０重
量部、（Ｂ）成分が６０〜２０重量部である。（Ｃ）成
分は（Ａ）と（Ｂ）成分との総＠１００＝１２−
重量部に対して、０．０１〜１０重量部、好ましくは０
．１〜８重量部である。In the composition of the present invention, the blending ratio of component (A) and component (B) is 0 to 90 parts by weight for component (A) and 90 parts by weight for component (B).
~IO parts by weight, preferably 30 to 70 parts by weight of component (A) and 60 to 20 parts by weight of component (B). Component (C) is 0.01 to 10 parts by weight, preferably 0
．． It is 1 to 8 parts by weight.
本発明の封着用光硬化性樹脂組成物は光の照射によって
硬化するが、光照射源としては太陽光線、低圧水銀灯、
高圧水銀灯、超高圧水銀灯、カーボンアーク灯、メタル
ハライドランプ、キセノンランプ等が用いられる。また
、必要に応じて光の照射時またはその前後に加熱を行っ
て硬化時間をより短くすることもできる。光を照射する
際の雰囲気は空気や窒素ガス、炭酸ガスまたは燃焼カス
等の不活性雰囲気でもよい。The photocurable resin composition for sealing of the present invention is cured by irradiation with light, and the light irradiation sources include sunlight, low-pressure mercury lamps,
High-pressure mercury lamps, ultra-high-pressure mercury lamps, carbon arc lamps, metal halide lamps, xenon lamps, etc. are used. Further, if necessary, heating can be performed during or before or after irradiation with light to further shorten the curing time. The atmosphere during irradiation with light may be an inert atmosphere such as air, nitrogen gas, carbon dioxide gas, or combustion residue.
（発明の効果）
本発明の光硬化性樹脂組成物は、少量の照射光量で硬化
し、液晶セルの製造工程を簡略化し、しかも短時間に製
造できる。製造された液晶セルの水分・熱等に対する化
学的・物理的安定性に優れ、特に耐熱性、耐水性、耐湿
性に優れている。本発明の封着用光硬化性樹脂組成物は
液晶セルの封着剤として特に好適であるが、その他の接
着、被覆等の用途に用いることもてきる。特に、液晶セ
ルを形成した後、透明電極と高密度多端子回路を接着す
るためのフィルム状接着剤として使用した場合、ポリエ
ステル結合に基づく適度の可撓性のために、より優れた
性能を発揮する。(Effects of the Invention) The photocurable resin composition of the present invention cures with a small amount of irradiation light, simplifies the manufacturing process of a liquid crystal cell, and can be manufactured in a short time. The manufactured liquid crystal cell has excellent chemical and physical stability against moisture, heat, etc., and is particularly excellent in heat resistance, water resistance, and humidity resistance. The photocurable resin composition for sealing of the present invention is particularly suitable as a sealant for liquid crystal cells, but it can also be used for other purposes such as adhesion and coating. In particular, when used as a film adhesive to bond transparent electrodes and high-density multi-terminal circuits after forming a liquid crystal cell, it exhibits better performance due to its moderate flexibility based on polyester bonds. do.
（実施例）
実施例を挙げて本発明を具体的に説明するが、本発明は
これら実施例のみに限定されるものではない。実施例中
部および％は特に指示しない限り重量に基づく。(Examples) The present invention will be specifically explained with reference to Examples, but the present invention is not limited only to these Examples. Examples and percentages are by weight unless otherwise indicated.
衷輿辺−Ｌ 封着用光硬化性樹脂組成物として次の配合を行った。Back side-L The following formulation was used as a photocurable resin composition for sealing.
灰分 １那−ダイマー酸変性
エポキシ樹脂 ６０エポキシ当量、６００〜
７００ｇ／ｅｑ分子景： １２００〜１４００
ビスフェノールＡ型エポキシ樹脂 １０分子量
１８００〜２０００
３．４−−エボキシンクロヘキシルメチル ２０３
°、４′−エボキシシクロヘキサンカルボギシレート
フェニルグリンジルエーテル １０γ−グリ
ノジルプロビルトリメトギノンラン ８芳香族スルポニ
ウム塩のプロピレン ４力−ボネート５０％溶液
これらの配合組成物をホモディスパーにて均一に溶解混
合した後、スペーサーのカラス繊維３部を混合して液晶
セル封着用光硬化性樹脂組成物を得ノこ。Ash content 1Na-dimer acid-modified epoxy resin 60 Epoxy equivalent, 600~
700g/eq Molecular weight: 1200-1400 Bisphenol A epoxy resin 10 Molecular weight
1800-2000 3.4--Evoxine chlorohexylmethyl 203
°, 4'-Eboxycyclohexane carboxylate phenyl grindyl ether 10 γ-Glynosylprobyl trimethogynone 8 Propylene 4-bonate 50% solution of aromatic sulfonium salt These blended compositions were homogenized using a homodisper. After melting and mixing, 3 parts of spacer glass fibers were mixed to obtain a photocurable resin composition for sealing a liquid crystal cell.
次に、この組成物を用いて下記に示す条件にて、硬化特
性を、さらに液晶セルの性能試験を行った。Next, using this composition, curing properties and liquid crystal cell performance tests were conducted under the conditions shown below.
〈硬化物特性測定〉
ＩＴＯ蒸着の１．Ｉｍｍ厚のパイレックスガラスに４ミ
ルのドクターブレードを用いて塗布し、超高圧水銀灯を
用いて２００ ｍＪ ７ｃｍ２で紫外線を照射して硬化
物を得た。硬化塗膜の硬度を鉛筆硬度により、さらにこ
の塗膜を接着試験機テンノロンＴ（ＴＭ−１００（東洋
ボールドウィン社製）によって垂直ハクリ接着強度を測
定した。<Measurement of properties of cured product> 1. of ITO vapor deposition. It was coated on Pyrex glass with a thickness of 1 mm using a 4 mil doctor blade and irradiated with ultraviolet rays at 200 mJ 7 cm 2 using an ultra-high pressure mercury lamp to obtain a cured product. The hardness of the cured coating film was measured using a pencil hardness, and the vertical peeling adhesive strength of the coating film was measured using an adhesion tester Tennoron T (TM-100 (manufactured by Toyo Baldwin)).
−１Ｆ＋−
〈液晶セル性能試験〉
ＩＴＯ蒸着の１．Ｉｍｍ厚のパイレックスガラス３ Ｘ
４ ｃｍ角」二に２００メツシユのスクリーン印刷に
より幅１００μ、塗布膜厚５０μになるようにセル外周
の形に印刷塗布した。更に、この」二にＩＴｏ蒸着パイ
レックスガラスを重ね合わせ、上下より加圧して圧着し
、超高圧水銀灯を用いて２００ｍＪ／ｃｍ”照射して接
着した。さらに液晶を封入し、」二記樹脂組成物を使用
して液晶注入孔を封入し、超高圧水銀灯を用いて紫外線
を照射して硬化し液晶セルを作製した。-1F+- <Liquid crystal cell performance test> 1. of ITO vapor deposition. Imm thick Pyrex glass 3X
The coating was applied in the shape of the outer periphery of the cell by screen printing with 200 meshes on a 4 cm square square so that the width was 100 μm and the coating thickness was 50 μm. Furthermore, ITo vapor-deposited Pyrex glass was superimposed on this "2", pressure was applied from above and below to bond it, and it was irradiated with 200 mJ/cm" using an ultra-high pressure mercury lamp to bond it.Furthermore, liquid crystal was encapsulated, and the resin composition described in "2" was bonded. A liquid crystal injection hole was sealed using a liquid crystal injection hole, and the liquid crystal cell was cured by irradiating ultraviolet rays using an ultra-high pressure mercury lamp.
次いで封止直後およびエージング（耐湿性テスト＝６５
℃×９０％（相対湿度）１０日間）時の垂直ハクリ試験
を実施した。また、封止直後および封止後８０℃で２時
間後の等方性処理を施し、液晶表示パターンの乱れの有
無を肉眼にて観察した。Then immediately after sealing and aging (moisture resistance test = 65
A vertical peeling test was conducted at 90% (°C x 90% (relative humidity) for 10 days). Immediately after sealing and 2 hours after sealing at 80° C., isotropic treatment was performed, and the presence or absence of disturbance in the liquid crystal display pattern was observed with the naked eye.
こうして配合した組成物のスクリーン印刷適性は良好で
、硬化物特性としては、鉛筆硬度６Ｈ。The composition blended in this way has good suitability for screen printing, and the cured product has a pencil hardness of 6H.
垂直ハクリ接着強度４０ｋｇ／ａｍ２以上でガラス基板
破壊となった。更に液晶セル性能試験では、封正直後、
エーノング共に垂直ハクリ強度は４０ｋｇ／ｃｍ２以」
−でガラス基板破壊となった。又封止直後および等方性
処理後の液晶表示パターンの乱れは無かった。The glass substrate broke when the vertical peeling adhesive strength exceeded 40 kg/am2. Furthermore, in the liquid crystal cell performance test, after sealing,
The vertical peeling strength of both Aenong and Ahnong is over 40kg/cm2.
- The glass substrate was destroyed. Further, there was no disturbance in the liquid crystal display pattern immediately after sealing and after isotropic treatment.
聚檄鰺点 封着用光硬化性樹脂組成物として次の配合を行った。Juyōmaji point The following formulation was used as a photocurable resin composition for sealing.
成次 貢静
ポリエステル樹脂変性エポキシ樹脂 ５０エポキン
当指・６００〜６５０ｙ／ｅｑ分子量： １２００〜１
３００
ビスフェノールＡ型エボキソ樹脂 ２０エボキノ
当指・９００〜１０００ｇ／ｅｑ水酸基数 ３．７個／
分子
分子量 １８００〜２０００
ビニルシクロヘキセンンオキサイド ３０γ−グリ
シンルプロピルトリメトキシシラン ８芳香族スルホニ
ウム塩のプロピレン ４力−ボネート５０％溶液
実施例１と同様に均一溶解して、液晶セル封着用光硬化
性樹脂組成物を得た。実施例１と同様の試験を実施した
結果、いずれも良好な結果であった。Naritsugu Kousei Polyester Resin Modified Epoxy Resin 50 Epokin Finger / 600-650y/eq Molecular Weight: 1200-1
300 Bisphenol A type eboxo resin 20 eboxo resin, 900-1000g/eq Number of hydroxyl groups 3.7 pieces/
Molecular weight 1800-2000 Vinyl cyclohexene oxide 30 γ-Glycinelupropyltrimethoxysilane 8 Aromatic sulfonium salt of propylene 50% solution of 4-carbonate Dissolved homogeneously in the same manner as Example 1 to obtain a photocurable resin for sealing liquid crystal cells A composition was obtained. As a result of carrying out the same test as in Example 1, all results were good.
Claims (1)
にグリシジルエーテル基を少な くとも１個有する樹脂、 （Ｂ）（Ａ）成分以外のエポキシ化合物、および （Ｃ）光照射によりカチオン重合開始能を 有する化合物 を含有する封着用光硬化性樹脂組成物。 ２、（Ａ）成分がダイマー酸変性エポキシ樹脂、ポリエ
ステル変性エポキシ樹脂またはそれらの混合物である第
１項記載の封着用光硬化性樹脂組成物。 ３、（Ｂ）成分が脂環式エポキシ化合物、芳香族エポキ
シ化合物またはそれらの混合物である第１項記載の封着
用光硬化性樹脂組成物。 ４、（Ａ）成分と（Ｂ）成分の合計量が１００重量部で
あって、その中で（Ａ）成分が１０〜９０重量部、（Ｂ
）成分が９０〜１０重量部であり、かつ（Ｃ）成分が（
Ａ）成分と（Ｂ）成分の合計量１００重量部に対し、０
．０１〜１０重量部である第１項記載の封着用光硬化性
樹脂組成物。[Claims] 1. (A) a resin having an ester bond in its main chain and at least one glycidyl ether group at the end of the molecule, (B) an epoxy compound other than component (A), and (C ) A photocurable resin composition for sealing containing a compound capable of initiating cationic polymerization upon irradiation with light. 2. The photocurable resin composition for sealing according to item 1, wherein component (A) is a dimer acid-modified epoxy resin, a polyester-modified epoxy resin, or a mixture thereof. 3. The photocurable resin composition for sealing according to item 1, wherein component (B) is an alicyclic epoxy compound, an aromatic epoxy compound, or a mixture thereof. 4. The total amount of component (A) and component (B) is 100 parts by weight, of which component (A) is 10 to 90 parts by weight, (B)
) component is 90 to 10 parts by weight, and component (C) is (
0 to 100 parts by weight of the total amount of component A) and component (B)
．． 2. The photocurable resin composition for sealing according to item 1, wherein the amount is 01 to 10 parts by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62086284A JPH0819215B2 (en) | 1987-04-07 | 1987-04-07 | Photocurable resin composition for sealing |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62086284A JPH0819215B2 (en) | 1987-04-07 | 1987-04-07 | Photocurable resin composition for sealing |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63251422A true JPS63251422A (en) | 1988-10-18 |
| JPH0819215B2 JPH0819215B2 (en) | 1996-02-28 |
Family
ID=13882531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62086284A Expired - Fee Related JPH0819215B2 (en) | 1987-04-07 | 1987-04-07 | Photocurable resin composition for sealing |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0819215B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0394231A (en) * | 1989-06-26 | 1991-04-19 | Matsushita Electric Ind Co Ltd | Color liquid crystal panel |
| JPH0543866A (en) * | 1991-08-20 | 1993-02-23 | Sony Chem Corp | Adhesive for liquid crystal sealing material |
| JP2001221998A (en) * | 1991-08-01 | 2001-08-17 | Seiko Epson Corp | Liquid crystal display element and electronic instrument |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56120726A (en) * | 1980-02-27 | 1981-09-22 | Toshiba Chem Corp | Epoxy resin composition having improved adhesiveness and cracking resistance |
| JPS61213217A (en) * | 1985-03-19 | 1986-09-22 | Nippon Soda Co Ltd | Photosetting resin composition for sealing |
| JPS61231022A (en) * | 1985-04-04 | 1986-10-15 | Nippon Soda Co Ltd | Photocurable sealing composition |
-
1987
- 1987-04-07 JP JP62086284A patent/JPH0819215B2/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56120726A (en) * | 1980-02-27 | 1981-09-22 | Toshiba Chem Corp | Epoxy resin composition having improved adhesiveness and cracking resistance |
| JPS61213217A (en) * | 1985-03-19 | 1986-09-22 | Nippon Soda Co Ltd | Photosetting resin composition for sealing |
| JPS61231022A (en) * | 1985-04-04 | 1986-10-15 | Nippon Soda Co Ltd | Photocurable sealing composition |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0394231A (en) * | 1989-06-26 | 1991-04-19 | Matsushita Electric Ind Co Ltd | Color liquid crystal panel |
| JP2001221998A (en) * | 1991-08-01 | 2001-08-17 | Seiko Epson Corp | Liquid crystal display element and electronic instrument |
| JPH0543866A (en) * | 1991-08-20 | 1993-02-23 | Sony Chem Corp | Adhesive for liquid crystal sealing material |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0819215B2 (en) | 1996-02-28 |
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| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |