JPS6310131A - Sealing composition for liquid crystal cell - Google Patents

Sealing composition for liquid crystal cell

Info

Publication number
JPS6310131A
JPS6310131A JP15412386A JP15412386A JPS6310131A JP S6310131 A JPS6310131 A JP S6310131A JP 15412386 A JP15412386 A JP 15412386A JP 15412386 A JP15412386 A JP 15412386A JP S6310131 A JPS6310131 A JP S6310131A
Authority
JP
Japan
Prior art keywords
epoxy resin
compd
liquid crystal
phosphate group
polythiol
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.)
Pending
Application number
JP15412386A
Other languages
Japanese (ja)
Inventor
Ichiro Matsui
松居 一郎
Koji Morishita
森下 浩二
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Bakelite Co Ltd
Original Assignee
Sumitomo Bakelite Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sumitomo Bakelite Co Ltd filed Critical Sumitomo Bakelite Co Ltd
Priority to JP15412386A priority Critical patent/JPS6310131A/en
Publication of JPS6310131A publication Critical patent/JPS6310131A/en
Pending legal-status Critical Current

Links

Abstract

PURPOSE:To obtain the improved adhesion stability against an undercoating layer etc., by incorporating a liquid epoxy resin contg. a phosphate group in the skeleton of the epoxy resin, a polythiol compd., 1-benzyl-2-methylimidazole as a hardening accelator and titanium oxide, etc., to the titled composition. CONSTITUTION:The titled composition comprises the liquid epoxy resin contg. the phosphate group in the epoxy resin skeleton, the polythiol compd., 1-benzyl-2- methylimidazole as the hardening accelerator, and titanium oxide and or silica. As the phosphate group contributes to the adhesion property against an ITO film, the adhesion stability against the sealing layer is remarkably increased by incorporating the liquid epoxy resin contg. the phosphate group to the titled composition. The polythiol compd. is exemplified by all compd. contg. >=2 -SH groups which has good compatibility against the epoxy resin. If the polythiol compd. is used to the hardener, as the -SH group contd. in said compd. has an antioxidability, the titled composition having good lightfastness, low temperature hardenability and flexibility is obtd.

Description

【発明の詳細な説明】 (産業上の利用分野) 本発明は液晶表示素子に用いられ液晶セル製造に際して
用いられるシール剤組成物に関するものである。更に詳
しくはその組成がリン酸エステル含有エポキシ液状物、
液状エポキシ樹脂・、ポリチオール系化合物、硬化促進
剤、無機充填剤から成るシール剤組成物に関するもので
ある。
DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a sealant composition used in liquid crystal display elements and used in manufacturing liquid crystal cells. More specifically, its composition is a phosphoric acid ester-containing epoxy liquid,
The present invention relates to a sealant composition comprising a liquid epoxy resin, a polythiol compound, a curing accelerator, and an inorganic filler.

(従来技術) 従来、液晶表示素子に用いられる液晶セルの透明導電基
板としては、ガラス上に酸化スズや酸化インジウム等を
蒸着やスパッタリングにより形成したものが用いられて
きた。しかしガラス基牟反は割れやすいという欠点を有
しているため、薄型化、軽量化、大面積化など近年液晶
表示素子に要求される特徴を十分に満たすことは難かし
かった。
(Prior Art) Conventionally, as a transparent conductive substrate of a liquid crystal cell used in a liquid crystal display element, a substrate in which tin oxide, indium oxide, or the like is formed on glass by vapor deposition or sputtering has been used. However, since glass substrates have the disadvantage of being easily broken, it has been difficult to fully satisfy the characteristics required of liquid crystal display elements in recent years, such as being thinner, lighter, and larger in area.

そこで、ガラス基板の代りに透明性を有する高分子フィ
ルム上に透明導電膜を形成したものを液晶表示素子の基
板として採用することが検討されてきている。
Therefore, instead of a glass substrate, consideration has been given to using a transparent conductive film formed on a transparent polymer film as a substrate for a liquid crystal display element.

この様な状況においてシール剤組成物に係る要求もガラ
ス基板を用いる場合とは様相を異にしてきており、具体
的には以下のことが要求されている。
Under such circumstances, the requirements regarding the sealant composition are also different from those when using a glass substrate, and specifically, the following are required.

(1)  プラスチックフィルム基板、透明導電膜、透
明導電膜の密着性を向上させるために設けられた下地層
等との密着性に優れていること。
(1) It has excellent adhesion to the plastic film substrate, the transparent conductive film, and the base layer provided to improve the adhesion of the transparent conductive film.

(2)プラスチックフィルム基板の採用のため、製造工
程、液晶セルの使用環境の変化などから、硬化物層が適
度の可撓性を有すること。
(2) Due to the adoption of a plastic film substrate, the cured material layer must have appropriate flexibility due to changes in the manufacturing process and the environment in which the liquid crystal cell is used.

(3)量産化および作業性の観点から適当な長さのポッ
トライフを有し、また低温速硬化可能であること。
(3) It should have an appropriate pot life from the standpoint of mass production and workability, and be capable of rapid curing at low temperatures.

(4)スクリーン印刷性に優れていること。(4) Excellent screen printability.

(5)耐液晶性に優れていること。(5) Excellent liquid crystal resistance.

(6)水蒸気、酸素等が液晶中に浸入することを防止で
きるものである。
(6) It can prevent water vapor, oxygen, etc. from entering the liquid crystal.

(7)液晶の作動に関して電流値増大の原因になるイオ
ン性不純物を含まない硬化物層であること。
(7) The cured layer does not contain ionic impurities that cause an increase in current value regarding the operation of the liquid crystal.

これらの要求に対して従来用いられてきたエポキシ−ポ
リアミン、エポシキ〜ポリアミド系のシール剤では満足
な結果は得られていなかった。
To meet these demands, the epoxy-polyamine and epoxy-polyamide sealants that have been used conventionally have not provided satisfactory results.

(発明の目的) 本発明は、これらの諸要求を満足するため、リン酸エス
テル基を含むエポキシ樹脂と通常のエポキシ樹脂を併用
した結果、優れたシール剤を得、更にこの知見に基づき
種々研究を進めて本発明を完成するに至ったものである
(Objective of the Invention) In order to satisfy these various requirements, the present invention uses an epoxy resin containing a phosphate ester group in combination with a normal epoxy resin to obtain an excellent sealant, and furthermore, based on this knowledge, various researches have been carried out. By proceeding with this process, we have completed the present invention.

(発明の構成) 本発明は、液晶セル製造に用いられるシール剤であって
その組成がエポキシ樹脂骨格中にリン酸エステル基が含
まれている液状エポキシ樹脂、ポリチオール系化合物、
硬化促進剤として1ベンジル−2メチルイミダゾール、
並びに酸化チタンおよび/またはシリカから成ることを
特徴とする液晶セル用シール剤組成物に関するものであ
る。通常の液晶セルにおいて、シール面は、用いる基板
あるいは透明導電膜の密着性を向上するために設けられ
た層、および透明導電膜(以下ITo膜と略記する)で
あるが、IT○膜面が親水性表面のため、リン酸エステ
ル基のないエポキシ系では密着性という点で若干問題が
あった。リン酸エステル基はITO膜との密着性に寄与
するため、リン酸エステルを含有する液状エポキシ樹脂
を使用することにより、シール層の密着安定性が著しく
向上する。更にリン酸エステル基のない他の液状のエポ
キシ樹脂を併用してもよい。
(Structure of the Invention) The present invention is a sealant used for manufacturing liquid crystal cells, the composition of which is a liquid epoxy resin containing a phosphoric acid ester group in the epoxy resin skeleton, a polythiol compound,
1-benzyl-2-methylimidazole as a curing accelerator;
The present invention also relates to a sealant composition for liquid crystal cells characterized by comprising titanium oxide and/or silica. In a normal liquid crystal cell, the sealing surface is a layer provided to improve the adhesion of the substrate or transparent conductive film used, and a transparent conductive film (hereinafter abbreviated as ITo film). Due to its hydrophilic surface, epoxy systems without phosphate groups had some problems in terms of adhesion. Since the phosphate ester group contributes to the adhesion with the ITO film, the use of a liquid epoxy resin containing a phosphate ester significantly improves the adhesion stability of the sealing layer. Furthermore, other liquid epoxy resins without phosphate groups may be used in combination.

また本発明においてポリチオール化合物としてはエキポ
ジ樹脂と相溶性の良好な2個以上の−SH基を含有する
化合物はすべて使用可能であり、硬化剤として該化合物
を用いると−SH基の酸化防止能に寄因して良好な耐光
性が得られ、更に低温硬化性、可撓性といった特徴が発
現する。具体的には以下の如き化合物が単独もしくは併
用して用いられ、エポキシ基1molに対して一3H基
1molの配合割合が一般的である。即ち2.2′−ジ
メチルメルカプトジエチルエーテル、ペンタエリスリト
ールβ−チオグリコレート、グリセリンβ−チオグルコ
レート、ソルビトールβ−チオグリコレート、トリスヒ
ドロキシエチル(βチオゲルコール)イソシアヌレート
、トリスヒドロキシエチル(メルカプトプロピル)イソ
シアヌレート、等である。
In addition, as the polythiol compound in the present invention, any compound containing two or more -SH groups that has good compatibility with the epoxy resin can be used, and when this compound is used as a curing agent, the antioxidant ability of the -SH group can be used. As a result, good light resistance is obtained, and characteristics such as low temperature curability and flexibility are exhibited. Specifically, the following compounds are used alone or in combination, and the compounding ratio is generally 1 mol of -3H group to 1 mol of epoxy group. Namely 2.2'-dimethylmercaptodiethyl ether, pentaerythritol β-thioglycolate, glycerin β-thioglucolate, sorbitol β-thioglycolate, trishydroxyethyl (β-thiogelcol) isocyanurate, trishydroxyethyl (mercaptopropyl) isocyanurate, etc.

次に本発明で用いられる硬化促進剤は酸無水物系エポキ
シ樹脂の硬化に際して用いられる促進剤はすべて使用で
きるが、イミダゾール系化合物、特に1ベンジル−2メ
チルイミダゾール(以後IB2MZと略記する)が好ま
しい。シール剤のポットライフと速硬化性は相反する特
性であるが182MZを使用することにより、適当な長
さのポットライフを保持しつつ、低温速硬化性も実現で
きる。また硬化時のシール内気泡の発生や、樹脂のにじ
み出しも起らなかった。
Next, as the curing accelerator used in the present invention, any accelerator used in curing acid anhydride-based epoxy resins can be used, but imidazole-based compounds, particularly 1-benzyl-2-methylimidazole (hereinafter abbreviated as IB2MZ) are preferred. . The pot life and fast curing properties of a sealant are contradictory characteristics, but by using 182MZ, it is possible to maintain an appropriate pot life while achieving low temperature fast curing properties. Furthermore, no air bubbles were generated within the seal during curing, and no resin oozed out.

また印刷性、印刷時のにじみ防止という観点から無機フ
ィラーの配合は不可欠であり、特にチタン白および/ま
たはシリカの添加は印刷時の直線性のチェックが出来る
という点で特に好ましい。
In addition, from the viewpoint of printability and prevention of bleeding during printing, it is essential to incorporate an inorganic filler, and addition of titanium white and/or silica is particularly preferable from the standpoint of being able to check linearity during printing.

またチタン白は紫外光吸収性を有しているために透過型
液晶デバイス等を得るに際してのバンクライト光に耐す
る極度の耐光性が発現するという点からも好ましい。
Furthermore, since titanium white has ultraviolet light absorbing properties, it is also preferable from the viewpoint that it exhibits extreme light resistance against bank light light when producing transmission type liquid crystal devices and the like.

(発明の効果) 得られたシール剤組成物は、前記諸要件を完全にクリヤ
ーする優れた硬化カール層を形成することができ好まし
い。
(Effects of the Invention) The obtained sealant composition is preferred because it can form an excellent cured curl layer that completely satisfies the above requirements.

(実施例) 溶融押し出し法により製膜したポリエーテルサルフォン
(以下PESと略記する)フィルムにアンダーコート処
理を施し、高周波マグネトロンスバッタリング装置を用
いて約300人の厚さにITO膜を形成し、透明導電基
板を作成した。該透明導電膜を6N−H(1!でエツチ
ングし、ITO膜のパターニングを行った。次に、イミ
ド系樹脂により配向膜を形成し、ラビング法により配向
処理を行った。
(Example) A polyether sulfone (hereinafter abbreviated as PES) film produced by melt extrusion was subjected to undercoat treatment, and an ITO film with a thickness of about 300 mm was formed using a high-frequency magnetron battering device. Then, a transparent conductive substrate was created. The transparent conductive film was etched with 6N-H (1!) to pattern the ITO film. Next, an alignment film was formed from an imide resin, and alignment treatment was performed by a rubbing method.

一方、以下の配合に従い、シール剤の主剤および硬化剤
を3本インクロールを用い混練して得た。
On the other hand, a sealant main ingredient and a curing agent were kneaded using three ink rolls according to the following formulation.

主剤配合組成 硬化剤配合組成 上記、主剤および硬化剤を100 : 95の割合で配
合しスクリーン印刷により、印刷中0.5mm 、印刷
厚み20μmとなるように、上部フィルム基板に塗布し
た。これを、10μm径のギャップ剤(ポリマービーズ
)を散布した下部基板と重ね合せ押圧して120℃、2
Hrs加熱硬化させた。硬化物のシール巾は1■であり
電掻間厚みは8〜9μmであった。
Main ingredient blend composition Hardener blend composition The above-mentioned base ingredient and hardener were blended in a ratio of 100:95 and applied to the upper film substrate by screen printing so that the printing thickness was 0.5 mm and the printing thickness was 20 μm. This was stacked and pressed with a lower substrate on which gap agent (polymer beads) with a diameter of 10 μm was sprinkled, and heated at 120°C for 2 hours.
Cured by heating for hours. The seal width of the cured product was 1 .mu.m, and the thickness between the electrodes was 8 to 9 .mu.m.

得られたセルのキャビティ内に真空注入法により液晶を
注入し、注入口をUV硬化樹脂で封止した。得られた液
晶セルは強固に完全にシールされており、可撓性を有す
る上に耐湿熱信頬性に優れた表示体として有用な液晶セ
ルであった。
Liquid crystal was injected into the cavity of the obtained cell by a vacuum injection method, and the injection port was sealed with a UV curing resin. The obtained liquid crystal cell was firmly and completely sealed, and was useful as a display body having flexibility and excellent humidity and heat resistance.

Claims (1)

【特許請求の範囲】[Claims] 液晶セルの製造に用いられるシール剤であって、その組
成がエポキシ樹脂骨格中にリン酸エステル基が含まれて
いる液状エポキシ樹脂、ポリチオール系化合物、硬化促
進剤として1ベンジル−2メチルイミダゾール、並びに
酸化チタンおよび/またはシリカから成ることを特徴と
する液晶セル用シール剤組成物。
A sealing agent used in the manufacture of liquid crystal cells, the composition of which is a liquid epoxy resin containing a phosphoric acid ester group in the epoxy resin skeleton, a polythiol compound, 1-benzyl-2-methylimidazole as a curing accelerator, and A sealant composition for a liquid crystal cell characterized by comprising titanium oxide and/or silica.
JP15412386A 1986-07-02 1986-07-02 Sealing composition for liquid crystal cell Pending JPS6310131A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP15412386A JPS6310131A (en) 1986-07-02 1986-07-02 Sealing composition for liquid crystal cell

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP15412386A JPS6310131A (en) 1986-07-02 1986-07-02 Sealing composition for liquid crystal cell

Publications (1)

Publication Number Publication Date
JPS6310131A true JPS6310131A (en) 1988-01-16

Family

ID=15577419

Family Applications (1)

Application Number Title Priority Date Filing Date
JP15412386A Pending JPS6310131A (en) 1986-07-02 1986-07-02 Sealing composition for liquid crystal cell

Country Status (1)

Country Link
JP (1) JPS6310131A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03189623A (en) * 1989-12-20 1991-08-19 Sumitomo Bakelite Co Ltd Sealing medium composition for liquid crystal cell
JPH07234411A (en) * 1994-02-21 1995-09-05 Casio Comput Co Ltd Liquid crystal display device and its production
US6153719A (en) * 1998-02-04 2000-11-28 Lord Corporation Thiol-cured epoxy composition
WO2008001695A1 (en) * 2006-06-26 2008-01-03 Panasonic Corporation Heat curable resin composition, and mounting method and reparing process for circuit board using the heat curable composition
JP2014173007A (en) * 2013-03-08 2014-09-22 Sekisui Chem Co Ltd Epoxy adhesive and lens-provided printed wiring board
WO2015025505A1 (en) * 2013-08-23 2015-02-26 株式会社Adeka One-part curable resin composition
JP2017226808A (en) * 2016-06-24 2017-12-28 株式会社Adeka One-liquid type curable resin composition and cured product thereof
CN109054711A (en) * 2018-08-10 2018-12-21 深圳飞世尔新材料股份有限公司 A kind of flexible screen frame envelope frame Wear Characteristics of Epoxy Adhesive mixture and preparation method thereof

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03189623A (en) * 1989-12-20 1991-08-19 Sumitomo Bakelite Co Ltd Sealing medium composition for liquid crystal cell
JPH07234411A (en) * 1994-02-21 1995-09-05 Casio Comput Co Ltd Liquid crystal display device and its production
US6153719A (en) * 1998-02-04 2000-11-28 Lord Corporation Thiol-cured epoxy composition
WO2008001695A1 (en) * 2006-06-26 2008-01-03 Panasonic Corporation Heat curable resin composition, and mounting method and reparing process for circuit board using the heat curable composition
JP5232645B2 (en) * 2006-06-26 2013-07-10 パナソニック株式会社 Thermosetting resin composition and circuit board mounting method and repair process using the same
JP2014173007A (en) * 2013-03-08 2014-09-22 Sekisui Chem Co Ltd Epoxy adhesive and lens-provided printed wiring board
WO2015025505A1 (en) * 2013-08-23 2015-02-26 株式会社Adeka One-part curable resin composition
CN105473633A (en) * 2013-08-23 2016-04-06 Adeka株式会社 One-part curable resin composition
JPWO2015025505A1 (en) * 2013-08-23 2017-03-02 株式会社Adeka One-part curable resin composition
CN105473633B (en) * 2013-08-23 2018-08-24 Adeka株式会社 One liquid type curable resin composition
US10144799B2 (en) 2013-08-23 2018-12-04 Adeka Corporation One-component curable resin composition
JP2017226808A (en) * 2016-06-24 2017-12-28 株式会社Adeka One-liquid type curable resin composition and cured product thereof
CN109054711A (en) * 2018-08-10 2018-12-21 深圳飞世尔新材料股份有限公司 A kind of flexible screen frame envelope frame Wear Characteristics of Epoxy Adhesive mixture and preparation method thereof

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