JPH0713175A - Sealing agent for liquid crystal - Google Patents
Sealing agent for liquid crystalInfo
- Publication number
- JPH0713175A JPH0713175A JP17367593A JP17367593A JPH0713175A JP H0713175 A JPH0713175 A JP H0713175A JP 17367593 A JP17367593 A JP 17367593A JP 17367593 A JP17367593 A JP 17367593A JP H0713175 A JPH0713175 A JP H0713175A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- sealing agent
- acrylate
- agent
- substrates
- 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
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 24
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 22
- 238000007789 sealing Methods 0.000 title abstract description 11
- 239000003822 epoxy resin Substances 0.000 claims abstract description 20
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 20
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 9
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims abstract description 6
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims abstract description 6
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims abstract description 5
- 239000003999 initiator Substances 0.000 claims abstract description 5
- 239000000565 sealant Substances 0.000 claims description 14
- 239000000758 substrate Substances 0.000 abstract description 12
- 238000003860 storage Methods 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 238000010438 heat treatment Methods 0.000 abstract description 3
- 230000007547 defect Effects 0.000 abstract description 2
- 238000001723 curing Methods 0.000 description 9
- 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 5
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 238000013007 heat curing Methods 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 3
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical group 0.000 description 3
- -1 glycidyl ester Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229940119545 isobornyl methacrylate Drugs 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000007519 polyprotic acids Polymers 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 description 1
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Substances FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003086 colorant Substances 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
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical class COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Liquid Crystal (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】この発明は、液晶シール剤に関す
る。This invention relates to a liquid crystal sealant.
【０００２】[0002]
【従来の技術】従来の例えば２枚の電極付き基板間に液
晶を封入した構造の液晶表示パネルは以下のようにして
作成されている。2. Description of the Related Art A conventional liquid crystal display panel having a structure in which liquid crystal is sealed between two substrates with electrodes is manufactured as follows.
【０００３】即ち、一方の電極付き基板にスクリーン印
刷又はディスペンサーによりシール剤を塗布し、ビーズ
状又はロッド状のスペーサー剤を介して他方の電極付き
基板を重ね合わせ、両者を加圧した状態でシール剤を硬
化させ、２枚の電極付き基板間に液晶を封入する。That is, one substrate with electrodes is coated with a sealant by screen printing or a dispenser, the other substrate with electrodes is superposed with a bead-shaped or rod-shaped spacer agent interposed therebetween, and both are sealed under pressure. The agent is cured and liquid crystal is sealed between the two substrates with electrodes.
【０００４】従来、シール剤としては、接着性、耐湿性
に優れた熱硬化型の一液エポキシ樹脂が用いられてい
る。Conventionally, as a sealant, a thermosetting type one-component epoxy resin having excellent adhesiveness and moisture resistance has been used.
【０００５】また、エポキシアクリレートを主成分とし
た光（紫外線）硬化性接着剤を用いることも提案されて
いる（特開平1-243029号公報）。It has also been proposed to use a light (ultraviolet) curable adhesive containing epoxy acrylate as a main component (Japanese Patent Laid-Open No. 1-243029).
【０００６】[0006]
【発明が解決しようとする問題点】しかし、シール剤と
して熱硬化型接着剤を用いると、耐湿性等の信頼性に関
しては優れているが、製造工程において硬化方法が加熱
硬化に約２時間以上という長時間を要するため、作業効
率が阻害される。However, when a thermosetting adhesive is used as the sealant, it is excellent in reliability such as moisture resistance, but in the manufacturing process, the curing method requires about 2 hours or more for heat curing. This requires a long time, which hinders work efficiency.
【０００７】また、予め位置合わせした２枚の基板間に
横方向のずれが生じたり、ギャップのばらつきが生じ
る。Further, a lateral shift occurs between two pre-aligned substrates, and a gap varies.
【０００８】一方、光（紫外線）硬化性樹脂を使用した
場合は硬化が常温、短時間で行えるため、シール剤の硬
化中に２枚の基板間に横方向にずれが生じたり、ギャッ
プのばらつきが生ずることがないが、従来使用されてき
たエポキシアクリレートを主成分とするものは接着力に
おいて十分に満足するものではなく、またポリエーテル
変性ウレタンアクリレートやポリエステル変性ウレタン
アクリレートを主成分とするものは耐湿性等の信頼性試
験において配向性を劣化させる等満足なものではなかっ
た。On the other hand, when a light (ultraviolet) curable resin is used, the curing can be carried out at room temperature in a short time, so that a lateral shift occurs between the two substrates during the curing of the sealant, and a gap variation. However, the epoxy acrylate-based ones that have been used in the past are not sufficiently satisfactory in adhesive strength, and the polyether-based urethane acrylate and polyester-modified urethane acrylates are the main components. In a reliability test such as humidity resistance, the orientation was deteriorated, which was not satisfactory.
【０００９】このため、光（紫外線）硬化官能基と熱硬
化官能基の両方を有するシール剤も提案されているが、
保存安定性が劣悪であったり、或は液晶表示パネルを製
造するに際して紫外線照射後、加熱硬化して液晶を封入
する工程を採用するため、一液エポキシ樹脂と比較して
も生産性が向上するまでには至らなかった。For this reason, a sealing agent having both a light (ultraviolet) curable functional group and a thermosetting functional group has been proposed.
The storage stability is poor, or when manufacturing a liquid crystal display panel, it adopts a process of encapsulating the liquid crystal by heat curing after irradiation with ultraviolet rays, so productivity is improved even when compared with a one-component epoxy resin. It didn't reach.
【００１０】[0010]
【問題点を解決するための手段】以上の問題点を解決す
るため、この発明では(A) イソボルニル（メタ）アクリ
レート、(B) エポキシアクリレート、(C) 光重合開始
剤、(D) 分子内に少なくとも一つ以上の重合可能なグリ
シジル基を有する化合物、(E) 潜在性熱硬化剤を必須成
分として含有する液晶シール剤を提案するものである。
案するものである。[Means for Solving the Problems] In order to solve the above problems, in the present invention, (A) isobornyl (meth) acrylate, (B) epoxy acrylate, (C) photopolymerization initiator, (D) intramolecular A liquid crystal sealant containing at least one compound having a polymerizable glycidyl group and (E) a latent thermosetting agent as an essential component.
It is a plan.
【００１１】この発明のシール剤組成物には前記以外の
成分として接着性を向上させるためのカップリング剤
や、粘度を調製するための無機充填剤や、ギャップを調
製するためのスペーサー剤を配合してもよい。A coupling agent for improving the adhesiveness, an inorganic filler for adjusting the viscosity, and a spacer agent for adjusting the gap are added to the sealant composition of the present invention as components other than the above. You may.
【００１２】また、(A) 項のイソボルニル（メタ）アク
リレートは以下の一般式（１）或は（２）で表される化
合物である。The isobornyl (meth) acrylate of the item (A) is a compound represented by the following general formula (1) or (2).
【００１３】[0013]
【化１】 [Chemical 1]
【００１４】(B) 項のエポキシ（メタ）アクリレートと
はエポキシ樹脂に、このエポキシ樹脂のエポキシ基とほ
ぼ当量の（メタ）アクリル酸を反応させて得られた物
質、或はエポキシ樹脂に、このエポキシ基とほぼ当量の
カルボキシル基を有する（メタ）アクリレートと多塩基
酸との混合物を反応させて得られた物質である。The epoxy (meth) acrylate in the item (B) is a substance obtained by reacting an epoxy resin with (meth) acrylic acid in an amount approximately equivalent to the epoxy groups of the epoxy resin, or an epoxy resin. It is a substance obtained by reacting a mixture of a (meth) acrylate having an epoxy group and an equivalent amount of a carboxyl group with a polybasic acid.
【００１５】このエポキシ（メタ）アクリレートとして
は、例えばビスフェノールＡ型ジグシジルエーテル型、
グリセリンジグリシジルエーテル型、ポリアルキレング
リコールジグリシジルエーテル型、多塩基酸ジグリシジ
ルエステル型、シクロヘキセンオキサイド型などエポキ
シ樹脂と（メタ）アクリル酸、またはカルボキシル基を
有する（メタ）アクリレートとの付加反応物を挙げるこ
とができる。Examples of the epoxy (meth) acrylate include bisphenol A type diglycidyl ether type,
Addition reaction products of epoxy resins such as glycerin diglycidyl ether type, polyalkylene glycol diglycidyl ether type, polybasic acid diglycidyl ester type, cyclohexene oxide type with (meth) acrylic acid or (meth) acrylate having a carboxyl group Can be mentioned.
【００１６】(C) 項の光重合開始剤としては、１−ヒド
ロキシシクロヘキシルフェニルケトン、２，２−ジメト
キシ−２−フェニルアセトフェノン、２−ヒドロキシ−
２−メチル−１−フェニルプロパン−１−オン、ジエト
キシアセトフェノン、２−メチル−１−（４−メチルチ
オフェニル）−２−モルホリノプロパン−１−オン、ベ
ンゾフェノン、ベンゾインイソプロピルエーテル、メチ
ルフェニルグリオキシレート等の紫外線を照射するとラ
ジカルを発生する化合物であればこの発明に使用でき
る。Examples of the photopolymerization initiator of the item (C) include 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy-2-phenylacetophenone and 2-hydroxy-
2-methyl-1-phenylpropan-1-one, diethoxyacetophenone, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one, benzophenone, benzoinisopropyl ether, methylphenylglyoxylate Compounds that generate radicals upon irradiation with ultraviolet rays such as the above can be used in the present invention.
【００１７】(D) 項の分子内に少なくとも一つ以上の重
合可能なグリシジル基を有する化合物としては、一分子
内にグリシジル基を一つ以上持つエポキシ樹脂、及びそ
のグリシジル基の開環重合によって生成するエポキシ樹
脂等を挙げることができるが、この発明においては特に
限定されない。The compound having at least one polymerizable glycidyl group in the molecule of the item (D) includes an epoxy resin having one or more glycidyl groups in one molecule, and ring-opening polymerization of the glycidyl group. Although the epoxy resin etc. which generate | occur | produce can be mentioned, it is not specifically limited in this invention.
【００１８】ここでエポキシ樹脂としては、例えばビス
フェノールＡ型エポキシ樹脂、ビスフェノールＦ型エポ
キシ樹脂、ビスフェノールＡＤ型エポキシ樹脂等やこれ
らを水添加したエポキシ樹脂、ノボラック型エポキシ樹
脂、（モノ）グリシジルエステル型エポキシ樹脂、ウレ
タン変性エポキシ樹脂、メタキシレンジアミンなどをエ
ポキシ化した含窒素エポキシ樹脂、ポリブタジエン或は
ＮＢＲなどを含有するゴム変性エポキシ樹脂を挙げるこ
とができるが、これらに限定されるものでなく、また固
状、液状を問わず使用することができる。Here, as the epoxy resin, for example, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol AD type epoxy resin or the like, or an epoxy resin obtained by adding them in water, novolac type epoxy resin, (mono) glycidyl ester type epoxy resin. Examples thereof include resins, urethane-modified epoxy resins, nitrogen-containing epoxy resins obtained by epoxidizing meta-xylenediamine, and rubber-modified epoxy resins containing polybutadiene, NBR, etc., but are not limited to these, and It can be used in any form, liquid or liquid.
【００１９】また、(E) 項の潜在性熱硬化剤としては、
ジシアンジアミド、二塩基酸ヒドラジド類、イミダゾー
ル類、イミダゾール・エポキシ付加物、三フッ化ホウ素
アミン錯体等一般に使用されている潜在性熱硬化剤を使
用することができる。Further, as the latent heat curing agent of the item (E),
Generally used latent thermosetting agents such as dicyandiamide, dibasic acid hydrazides, imidazoles, imidazole / epoxy adducts, boron trifluoride amine complex can be used.
【００２０】また、この発明に係る液晶シール剤には上
記の成分以外にも必要に応じて種々の添加剤を加えるこ
とができ、例えば接着力向上を目的としてカップリング
剤やビス［（２−ヒドロキシエチル）メタクリレート］
アシッド・フォスフェート等のリン化合物や染料や顔料
等の着色剤や、重合禁止剤、酸化防止剤、レベリング
剤、粘度を調整するための無機充填剤、ギャップを調製
するためのスペーサー剤等を加えることも可能である。In addition to the above-mentioned components, various additives may be added to the liquid crystal sealant according to the present invention as required. For example, a coupling agent or bis [(2- Hydroxyethyl) methacrylate]
Add phosphorus compounds such as acid phosphates, coloring agents such as dyes and pigments, polymerization inhibitors, antioxidants, leveling agents, inorganic fillers for adjusting viscosity, spacer agents for adjusting gaps, etc. It is also possible.
【００２１】更に、この発明によれば液晶表示パネルの
製造に際して２枚の電極付き基板に液晶シール剤を挟ん
で重ね合わせた状態で光（紫外線）を照射してシール剤
を一次硬化させ、次に２枚の電極基板間に液晶を封入し
たのち、等方性加熱処理によってシール剤を完全硬化さ
せることができるため、シール剤の硬化のために長時間
加熱する必要がなく、従来の一液エポキシ樹脂と比較し
て、生産性を向上させることができる。Further, according to the present invention, when manufacturing a liquid crystal display panel, light (ultraviolet rays) is irradiated on the two electrode-attached substrates with the liquid crystal sealant sandwiched therebetween to cause primary curing of the sealant. Since the sealing agent can be completely cured by isotropic heat treatment after enclosing the liquid crystal between the two electrode substrates in 1st, there is no need to heat for a long time to cure the sealing agent. The productivity can be improved as compared with the epoxy resin.
【００２２】[0022]
【実施例】以下、この発明の実施例及び比較例を表１に
示す。実施例１、２は光（紫外線）硬化成分の他に熱硬
化成分であるイソボルニルメタクリレートを配合して、
保存安定性、接着性、配向性等を確認した。EXAMPLES Examples and comparative examples of the present invention are shown in Table 1 below. In Examples 1 and 2, the thermosetting component isobornyl methacrylate was blended in addition to the light (ultraviolet) curing component,
The storage stability, adhesiveness, orientation, etc. were confirmed.
【００２３】比較例１、２はイソボルニルメタクリレー
トの代わりに２−ヒドロキシエチルメタクリレートを配
合して、保存安定性、接着性、配向性等を確認した。In Comparative Examples 1 and 2, 2-hydroxyethyl methacrylate was blended in place of isobornyl methacrylate, and storage stability, adhesiveness, orientation and the like were confirmed.
【００２４】[0024]
【表１】 [Table 1]
【００２５】これによれば、実施例１、２では光（紫外
線）硬化成分と熱硬化成分の配合比を変えているが、モ
ノマー成分としてイソボルニルメタクリレートを用いて
いるので、保存安定性は常温で３ケ月以上の保存が可能
であり、充分に実用のレベルにあり、また硬化後のパネ
ルとしての性能も耐熱性、耐湿性ともに良好な結果が得
られている。According to this, in Examples 1 and 2, the mixing ratio of the light (ultraviolet) curing component and the thermosetting component was changed, but since isobornyl methacrylate was used as the monomer component, the storage stability was It can be stored at room temperature for 3 months or more, is at a practically sufficient level, and has good heat resistance and humidity resistance as a panel after curing.
【００２６】一方、比較例１、２の場合は保存安定性が
極端に悪くなり、また光（紫外線）硬化後、液晶を封入
して等方性処理時に熱硬化させる工程を採った場合には
耐熱時の配向性が悪くなる。On the other hand, in the case of Comparative Examples 1 and 2, the storage stability becomes extremely poor, and when a process of encapsulating liquid crystal after light (ultraviolet) curing and heat curing during the isotropic treatment is adopted. Orientation deteriorates when heat is applied.
【００２７】[0027]
【発明の効果】以上詳述したように、この発明に係る液
晶シール剤はシール剤として本来必要とされる接着性、
耐湿性、耐熱性に優れ、高温高湿動作等においても配向
不良などを起こさないという優れた特性の他に、保存安
定性においても優れた特性を有している。As described above in detail, the liquid crystal sealant according to the present invention has the adhesiveness originally required as a sealant,
It has excellent moisture resistance and heat resistance, and does not cause misalignment during high temperature and high humidity operation, and also has excellent storage stability.
【００２８】また、この発明に係る液晶シール剤によれ
ば、液晶表示パネルの製造に際して紫外線で一次硬化
し、液晶封入後、等方性処理等の熱で完全硬化させるこ
とができるため、従来の一液エポキシ樹脂と比較して、
生産性を向上させることができ、しかも基板間の位置ず
れやギャップ不良をなくすことができるため、高信頼性
の液晶表示パネルを得ることができる。Further, according to the liquid crystal sealant of the present invention, it is possible to perform primary curing with ultraviolet rays in the production of a liquid crystal display panel and completely cure it with heat such as isotropic treatment after encapsulating the liquid crystal. Compared with one-pack epoxy resin,
Since the productivity can be improved and the positional deviation between the substrates and the gap defect can be eliminated, a highly reliable liquid crystal display panel can be obtained.
Claims (1)
ト、(B) エポキシアクリレート、(C) 光重合開始剤、
(D) 分子内に少なくとも一つ以上の重合可能なグリシジ
ル基を有するエポキシ樹脂、(E) 潜在性熱硬化剤を必須
成分として含有することを特徴とする液晶シール剤。1. An (A) isobornyl (meth) acrylate, (B) an epoxy acrylate, (C) a photopolymerization initiator,
(D) An epoxy resin having at least one polymerizable glycidyl group in the molecule, and (E) a latent thermosetting agent as an essential component, which is a liquid crystal sealant.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5173675A JP3024440B2 (en) | 1993-06-22 | 1993-06-22 | Liquid crystal sealant |
| GB9412354A GB2279656B (en) | 1993-06-22 | 1994-06-20 | Sealing compound for liquid crystal |
| TW083105546A TW351729B (en) | 1993-06-22 | 1994-06-20 | Sealing compound for liquid crystal |
| DE4421621A DE4421621A1 (en) | 1993-06-22 | 1994-06-21 | Sealant for liquid crystals |
| KR1019940014228A KR950001363A (en) | 1993-06-22 | 1994-06-22 | Liquid crystal sealing agent |
| US08/441,376 US5596024A (en) | 1993-06-22 | 1995-04-18 | Sealing composition for liquid crystal |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5173675A JP3024440B2 (en) | 1993-06-22 | 1993-06-22 | Liquid crystal sealant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0713175A true JPH0713175A (en) | 1995-01-17 |
| JP3024440B2 JP3024440B2 (en) | 2000-03-21 |
Family
ID=15965019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5173675A Expired - Fee Related JP3024440B2 (en) | 1993-06-22 | 1993-06-22 | Liquid crystal sealant |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3024440B2 (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6037155A (en) * | 1997-02-27 | 2000-03-14 | Nippon Soda Co., Ltd. | Process for preparing α-hydroxy acids using microorganism and novel microorganism |
| JP2006350249A (en) * | 2005-06-20 | 2006-12-28 | Sekisui Chem Co Ltd | Curable resin composition for liquid crystal dropping method, sealing agent for liquid crystal dropping method, vertical conduction material, and liquid crystal display element |
| US7253131B2 (en) | 2001-05-16 | 2007-08-07 | Sekisui Chemical Co., Ltd. | Curing resin composition and sealants and end-sealing materials for displays |
| EP1598897A4 (en) * | 2003-02-20 | 2010-09-01 | Nippon Kayaku Kk | SEALING AGENT FOR PHOTOELECTRIC CONVERSION ELEMENT AND PHOTOELECTRIC CONVERSION ELEMENT USING THE SAME |
| US7829605B2 (en) | 2005-05-31 | 2010-11-09 | Denki Kagaku Kogyo Kabushiki Kaisha | Energy ray-curable resin composition and adhesive using same |
| JP2011141576A (en) * | 2011-04-20 | 2011-07-21 | Sekisui Chem Co Ltd | Curable resin composition for one drop fill, sealant for one drop fill, vertical conduction material, and liquid crystal display element |
| JP6114893B1 (en) * | 2015-10-26 | 2017-04-12 | 積水化学工業株式会社 | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element |
| JP2018536079A (en) * | 2015-10-19 | 2018-12-06 | サエス・ゲッターズ・エッセ・ピ・ア | Curable adhesive composition for flexible substrates |
-
1993
- 1993-06-22 JP JP5173675A patent/JP3024440B2/en not_active Expired - Fee Related
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6037155A (en) * | 1997-02-27 | 2000-03-14 | Nippon Soda Co., Ltd. | Process for preparing α-hydroxy acids using microorganism and novel microorganism |
| US7253131B2 (en) | 2001-05-16 | 2007-08-07 | Sekisui Chemical Co., Ltd. | Curing resin composition and sealants and end-sealing materials for displays |
| EP1598897A4 (en) * | 2003-02-20 | 2010-09-01 | Nippon Kayaku Kk | SEALING AGENT FOR PHOTOELECTRIC CONVERSION ELEMENT AND PHOTOELECTRIC CONVERSION ELEMENT USING THE SAME |
| US7915524B2 (en) | 2003-02-20 | 2011-03-29 | Nippon Kayaku Kabushiki Kaisha | Sealing agent for photoelectric conversion device and photoelectric conversion device using the same |
| US7829605B2 (en) | 2005-05-31 | 2010-11-09 | Denki Kagaku Kogyo Kabushiki Kaisha | Energy ray-curable resin composition and adhesive using same |
| JP2006350249A (en) * | 2005-06-20 | 2006-12-28 | Sekisui Chem Co Ltd | Curable resin composition for liquid crystal dropping method, sealing agent for liquid crystal dropping method, vertical conduction material, and liquid crystal display element |
| JP2011141576A (en) * | 2011-04-20 | 2011-07-21 | Sekisui Chem Co Ltd | Curable resin composition for one drop fill, sealant for one drop fill, vertical conduction material, and liquid crystal display element |
| JP2018536079A (en) * | 2015-10-19 | 2018-12-06 | サエス・ゲッターズ・エッセ・ピ・ア | Curable adhesive composition for flexible substrates |
| JP6114893B1 (en) * | 2015-10-26 | 2017-04-12 | 積水化学工業株式会社 | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element |
| WO2017073548A1 (en) * | 2015-10-26 | 2017-05-04 | 積水化学工業株式会社 | Sealing agent for liquid crystal display elements, vertically conducting material and liquid crystal display element |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3024440B2 (en) | 2000-03-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5596024A (en) | Sealing composition for liquid crystal | |
| JP5008682B2 (en) | Sealant for liquid crystal dropping method containing photo-curing resin and thermosetting resin | |
| JP5522938B2 (en) | Manufacturing method of liquid crystal display panel | |
| KR100238018B1 (en) | Seal materials for liquid crystal display panel and liquid crystal display panel for using therefor | |
| JP4531566B2 (en) | Liquid crystal sealant composition and method for producing liquid crystal display panel using the same | |
| KR20130125788A (en) | Compound suitable for photopolymerization initiator, photopolymerization initiator, and photocurable resin composition | |
| WO2005052021A1 (en) | One-pack-type resin composition curable with combination of light and heat and use of the same | |
| JPWO2003073158A1 (en) | Manufacturing method of liquid crystal display cell and sealing agent for liquid crystal display cell | |
| JP2010020286A (en) | Sealing agent for liquid crystal dropping technology and method of manufacturing liquid crystal display | |
| JP2008179796A (en) | Compound having (meth) acryloyl group and glycidyl group, and polymerizable composition containing the compound | |
| EP0646632A1 (en) | A method of manufacturing a liquid crystal display and a composition for use in the method | |
| JP6014325B2 (en) | Sealant for organic electroluminescence display element | |
| JPH0713175A (en) | Sealing agent for liquid crystal | |
| JPH0713173A (en) | Sealing agent for liquid crystal | |
| JP3863253B2 (en) | Liquid crystal display element and manufacturing method thereof | |
| KR101227206B1 (en) | Curable composition | |
| JPS6151024A (en) | Photocurable sealing resin composition | |
| JPWO2009075273A1 (en) | Manufacturing method of liquid crystal display device | |
| JP3856746B2 (en) | Sealant composition for liquid crystal display device | |
| KR20190103351A (en) | Radiation curable sealant compositions | |
| KR101599068B1 (en) | Sealing agent for liquid crystal dropping method and manufacturing method of liquid crystal display device | |
| JP2007003911A (en) | Sealant for liquid crystal dropping method, vertical conduction material, and liquid crystal display element | |
| JPS6176521A (en) | Photo-setting resin composition for sealing | |
| JP2021113944A (en) | Sealant for liquid crystal dropping method | |
| JPS61213217A (en) | Photosetting resin composition for sealing |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |