JPS62133425A - Composition of sealing material for liquid crystal cell - Google Patents

Composition of sealing material for liquid crystal cell

Info

Publication number
JPS62133425A
JPS62133425A JP27333385A JP27333385A JPS62133425A JP S62133425 A JPS62133425 A JP S62133425A JP 27333385 A JP27333385 A JP 27333385A JP 27333385 A JP27333385 A JP 27333385A JP S62133425 A JPS62133425 A JP S62133425A
Authority
JP
Japan
Prior art keywords
epoxy resin
liquid crystal
sealing material
compd
liquid epoxy
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
JP27333385A
Other languages
Japanese (ja)
Inventor
Setsuo Suzuki
節夫 鈴木
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 JP27333385A priority Critical patent/JPS62133425A/en
Publication of JPS62133425A publication Critical patent/JPS62133425A/en
Pending legal-status Critical Current

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  • Liquid Crystal (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Epoxy Resins (AREA)

Abstract

PURPOSE:To satisfy completely several conditions required for screen-printing a sealing material on a substrate surface, and for heat-curing after lamination by constituting a compsn. of the sealing material for a liquid crystal cell of liquid epoxy resin contg. phosphoric ester groups in the skeletal structure of the epoxy resin, usual liquid epoxy resin, a polythiol compd., a curing accelerator, and an inorg. filler. CONSTITUTION:The compsn. consists of a liquid epoxy resin, liquid epoxy compd. contg. phosphoric ester, a polythiol compd., a curing accelerator, and an inorg. filler. The epoxy resin in the sealing material compsn. is necessary to be a mixture of a liquid epoxy resin contg. phosphoric ester group in combination with a liquid epoxy resin. The phosphoric ester group contained in the epoxy resin contributes to increase adhesive strength of the sealing material to an ITO electrode, so the stability of the adhesive property of the sealing layer is improved remarkably. Any polythiol compd. contg. >=2 -SH groups having sufficient compatibility to epoxy resin may be useful. When this compd. is used for a curing agent, satisfactory light resistance is realized due to the oxidation preventing effect of the -SH group. Furthermore, low temp. curing property, and flexibility are improved characteristically.

Description

【発明の詳細な説明】 〔産業上の利用分野〕 本発明は表示体に用いられる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り、更に詳しく
はその組成物が液状工lキシ樹脂、燐酸エステル含有エ
ノキシ液状物、ヒ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係るものである。
DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a sealant composition used in the production of liquid crystal cells used in display bodies, and more specifically, the present invention relates to a sealant composition that is used in the production of liquid crystal cells used in display bodies, and more specifically, the composition is composed of a liquid synthetic resin, The present invention relates to a sealant composition comprising a phosphoric acid ester-containing enoxy liquid, a hiritiol compound, a curing accelerator, and an inorganic filler.

〔従来技術) 従来液晶セルは対向するvl極を有する2枚の配向膜付
き基板によシ形成されるキャビティ(キャビティ厚5〜
10μm)の4周は液晶注入孔′に残こしてシールし、
該キャビティ内に液晶分封入し、次いで封入口を紫外線
硬化樹脂で封じて得られるのが一般的であシ、配向膜付
き[極基板としてはガラス若しくはプラスチックフィル
ムが用いられている。
[Prior art] A conventional liquid crystal cell has a cavity (cavity thickness 5 to
10 μm) was left in the liquid crystal injection hole and sealed.
It is generally obtained by enclosing the liquid crystal in the cavity, and then sealing the enclosing port with an ultraviolet curing resin, with an alignment film attached (a glass or plastic film is used as the polar substrate).

一方近年に到液晶セルの薄型化が、液晶表示体の軽薄化
、大型化に伴なう視野角の増大という動向から、強く望
まれ、ガラス基板厚み減少化、又はプラスチックフィル
ム基板の採用という動きが急である。
On the other hand, in recent years, there has been a strong desire to make liquid crystal cells thinner due to the trend of increasing viewing angles due to lighter and thinner liquid crystal displays and larger sizes, and there is a trend toward reducing the thickness of glass substrates or adopting plastic film substrates. is sudden.

この様な状況においてシール層に係る要求も様相を異に
して来ており、これに対する対応が強く望まれる様にな
りつつある。
Under these circumstances, the requirements regarding the sealing layer have changed in appearance, and there is a strong desire to respond to these requirements.

即ち、具体的には、以下のことが要求されてきている。That is, specifically, the following has been required.

1液晶セルの大型化に伴ないセル面積に占めるシール層
の面積の割合が極端に小さくなシ基板と一ル層が形成さ
れなければならない。
As liquid crystal cells become larger, it is necessary to form a substrate and a layer in which the ratio of the area of the seal layer to the cell area is extremely small.

2、基板厚みの減少、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等からシ
ール層、に適度の可撓性を付与する必要がある。
2. Due to the reduction in substrate thickness and the adoption of plastic film substrates, it is necessary to provide the sealing layer with 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イツトライフを有し
低温速硬化可能なシール剤が必要である。
3. From the viewpoint of mass production and workability, there is a need for a sealant that has a long shelf life and can be cured quickly at low temperatures.

4、キャビティ形成後液晶を封入する為液晶に関して不
活性なシール剤であることが必須である。
4. Since the liquid crystal is sealed after the cavity is formed, it is essential that the sealant be inactive with respect to the liquid crystal.

5、透過型液晶表示体が主流となる丸めシール剤はバッ
クライトに耐える高度の耐光性、耐熱性が要求される。
5. Rounding sealants, which are mainly used for transmissive liquid crystal displays, are required to have high light resistance and heat resistance to withstand backlight.

6、液晶セル面積の有効利用のため狭い線巾のシール層
であることが必要となシ、シャープな直線性を有するシ
ール層であること。
6. In order to effectively utilize the area of the liquid crystal cell, the seal layer must have a narrow line width, and the seal layer must have sharp linearity.

これらの可酷な要求に対して従来用いられて来た工Iキ
シ〜イリアミン、エイキシ〜ぜリアミド系のシール剤で
は満足することが出来なかった。
These severe requirements could not be met with the conventionally used sealants based on polyamides and polyamides.

〔発明の目的〕[Purpose of the invention]

本願発明者らはこれらの#&要要求温満足ることの出来
るシール剤を得んとして鋭意研究を行ない、ポリチオー
ル−エポキシ樹脂系の組成物の優れていることを見い出
し先に出願した。然しなから170g面が親水性表面の
ため通常のエピキシ系では密着性という点で若干難点が
ある為鋭意この点についての改良検討を行ない、燐酸エ
ステル基を含有するニーキシ樹脂の併用が優れた改良効
果の有ることを見い出し本願発明に到達した。
The inventors of the present application conducted extensive research in an effort to obtain a sealant that could satisfy these # and required temperature requirements, and after discovering the superiority of a polythiol-epoxy resin composition, filed an application. However, since the 170g surface is a hydrophilic surface, there are some difficulties in terms of adhesion with normal epixy systems, so we conducted intensive studies to improve this point, and found that the combination of nixy resin containing phosphate ester groups was an excellent improvement. We have found that this is effective and have arrived at the present invention.

し発明の構成〕 本発明によるシール剤組成物中のエゼキシ樹111は液
状エイキシ樹脂と燐酸エステルを含有する液状エポキシ
樹脂の併用が必須である。
Structure of the Invention] The epoxy resin 111 in the sealant composition according to the present invention must be a combination of a liquid epoxy resin and a liquid epoxy resin containing a phosphoric acid ester.

即ちエダキシ側脂中に含有される燐酸エステル基は強度
のITO電極との密着性に寄与するためシール!−の密
着安定性が著しるしく向上する。一方燐酸基含有エボキ
シ樹脂のみでは粘度が増大し印刷性に劣るという欠点が
生じてしまう。
In other words, the phosphoric acid ester group contained in the edoxy side fat contributes to strong adhesion with the ITO electrode, making it a seal! - The adhesion stability is significantly improved. On the other hand, using only a phosphoric acid group-containing epoxy resin has the disadvantage of increased viscosity and poor printability.

また本発明においてタリチオール化合物としてはエンげ
キシ樹脂と相溶性の良好な2個以上の一5H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
物全周いると−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1(、、x4キシ基1 molに対して
一8H基1 motの配合1刊合が一般的である。即ち
2,2′−ジメチルメルカプトジエチルエーテル、イン
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)インシアヌレート、等である。
In addition, in the present invention, any compound containing two or more 15H groups that has good compatibility with the engeki resin can be used as the talythiol compound, and if the compound is present all around the compound as a curing agent, the -SH group can be oxidized. Good light resistance can be obtained due to the prevention ability, and characteristics such as low-temperature curability and flexibility are also exhibited. Specifically, the following compounds are used alone or in combination, and the general formula is 1 mole of 18H group to 1 mol of x4xy group. That is, 2,2'- Dimethyl mercapto diethyl ether, intererythritol β-thioglycolate, glycerin β
-thioglucorate, sorbitol β-thioglycolate, trishydroxyethyl (βthiogelcol) isocyanurate, trishydroxyethyl (mercaptopropyl)in cyanurate, and the like.

次いで本願発明で用いられる硬化促進Mとしては酸無水
物系ニーキシ樹脂の硬化に際して用いられる促進剤はす
べて使用出来るが特に2エチル−4−メチルイミダゾー
ル等のイミダゾール系化合物(以下2E4klZという
> 2.4,6 )す(ジメチルアミンメチル)フェノ
ール(以下’rAPという)等のアミン化合物が好まし
い。
Next, as the curing accelerator M used in the present invention, all accelerators used in curing acid anhydride-based Nixy resin can be used, but in particular, imidazole-based compounds such as 2-ethyl-4-methylimidazole (hereinafter referred to as 2E4klZ>2.4 , 6) Amine compounds such as (dimethylamine methyl) phenol (hereinafter referred to as 'rAP) are preferred.

また2液(工J?キシ側脂およびぼりテール)混合後の
イツトライフと硬化速度の向上との両立化のため上記化
合物の塩が潜伏性促進剤として好ましく、特に2E4M
Zとトリフェニルフォスファイトの塩、およびTAPと
カルボキシル基を有するエチレン性2ffi結合を有す
る化合物の塩が好ましい。
In addition, salts of the above compounds are preferred as latent accelerators, especially 2E4M, in order to improve the hardness and curing speed after mixing the two liquids (KJ-Kishi side fat and streamtail).
Salts of Z and triphenylphosphite and TAP and salts of compounds having an ethylenic 2ffi bond with a carboxyl group are preferred.

これら促進AQは厘温で安定なため安定なイットラ7が
あるにも係らず80℃以上の温度で急激に解離し速硬化
性を示す。
These accelerated AQs are stable at ambient temperatures, and therefore rapidly dissociate at temperatures of 80° C. or higher, exhibiting rapid curing properties, despite the presence of stable Ittra 7.

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シ、特にチタン白の添加は印
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。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金得るに際してのバックライト光に
酎する極度の耐光性が発現するという点からも好ましい
Further, from the viewpoint of printability and prevention of bleeding during printing, the addition of an inorganic filler is essential, and the addition of titanium white is particularly preferable from the standpoint that linearity during printing can be checked. Further, since titanium white has ultraviolet light absorbing properties, it is preferable from the viewpoint that it exhibits extreme light resistance to backlight light when producing gold for transmission type liquid crystal devices, etc.

〔発明の効果〕〔Effect of the invention〕

得られた配合組成物は基板面上にスクリーン印刷され次
いで貼シ合せ後加熱硬化せしめられる前記諸要件を完全
にクリヤーする優れた硬化シール層を形成することが出
来る優れた組成物である。
The resulting blended composition is an excellent composition that can form an excellent cured sealing layer that completely satisfies the above-mentioned requirements when it is screen printed on the substrate surface and then heat-cured after lamination.

以下に実施例を示す。Examples are shown below.

実施例1 溶融押し出し法により得られた非旋光性ポリエーテルサ
ルフォノフィルム上にスノZツタ法によシインジウム〜
錫酸化薄膜を形成した、(シート抵抗380Ω/口)次
いで該薄膜を通常のエツチング法を用いて電極および端
正部から成る回路を形成した後回路面上をイミド系樹脂
によシ配向膜処理を施こした。
Example 1 Cyindium was deposited on a non-optically active polyether sulfono film obtained by a melt extrusion method by the Snow Z-vine method.
A tin oxide thin film was formed (sheet resistance: 380 Ω/unit). Next, a circuit consisting of electrodes and edge parts was formed using the thin film using a normal etching method. After that, an alignment film treatment was performed on the circuit surface using an imide resin. I did it.

次いで該Iul路板上板上本インクロールで混練された
以下の配合の主剤・硬化剤全配合した配合物をスクリー
ン印刷により液晶注入口を残こして印刷した。印刷中は
0.5 ttrtnであり印刷厚みは20μmであった
Next, a mixture of the main ingredient and curing agent having the following composition, which had been kneaded with an ink roll on the Iul road board upper plate, was printed by screen printing, leaving the liquid crystal injection port. During printing, the printing speed was 0.5 ttrtn, and the printing thickness was 20 μm.

主剤配合組成 硬化剤配合組成 主剤/硬化剤配合比= 100 / 95次いで上部回
路板(PES / ITO回路板)を10μmのギャッ
プ剤を介して重ね合せ押圧して120’C2hrs 加
熱硬化させた。
Base component composition Hardener composition Main component/curing agent blend ratio = 100/95 Next, the upper circuit board (PES/ITO circuit board) was pressed together with a gap agent of 10 μm interposed therebetween and heat-cured for 120'C2hrs.

硬化物のシール巾は1冒であシミ極間厚みは6〜7μm
であった。
The seal width of the cured product is 1 inch, and the thickness between the stains is 6 to 7 μm.
Met.

次いで真空下で上記貼せ物のキャビティ内に注入口から
液晶を注入し、注入口金Uv硬化樹脂で封じた。得られ
た液晶セルは強固に完全にシールされておシ、可撓性を
有する上に耐湿熱信頼性に優れた表示体として有用な液
晶セルであった。
Next, liquid crystal was injected into the cavity of the pasted product from the injection port under vacuum, and the injection port was sealed with UV curing resin. The obtained liquid crystal cell was strongly and completely sealed, had flexibility, and was useful as a display body with excellent moisture and heat resistance reliability.

Claims (3)

【特許請求の範囲】[Claims] (1)対向したインジウム−錫酸化物薄膜電極を具備す
る2枚の配向膜付き基板の4周をシールして一定のキャ
ビティを形成して、該キャビティ内に液晶セルを封入す
る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燐酸エステル基が含まれてい
る液状エポキシ樹脂、通常の液状エポキシ樹脂、ポリチ
オール系化合物、硬化促進剤、無機充填剤、から成るこ
とを特徴とする液晶セル用シール剤
(1) Manufacturing a liquid crystal cell by sealing the four peripheries of two substrates with alignment films equipped with opposing indium-tin oxide thin film electrodes to form a certain cavity, and enclosing the liquid crystal cell within the cavity. It is a sealing agent used in Features of sealant for liquid crystal cells
(2)硬化促進剤が2エチル−4メチルイミダゾールと
トリフェニルフォスファイトの組合せである特許請求の
範囲第1項記載の液晶セル用シール剤組成物
(2) The sealant composition for a liquid crystal cell according to claim 1, wherein the curing accelerator is a combination of 2-ethyl-4-methylimidazole and triphenylphosphite.
(3)硬化促進剤が2,4,6トリ(デイメチルアミノ
メチル)フェノールと分子内にエチレン性2重結合を有
し且つ−COOH基を有している化合物との塩である特
許請求の範囲第1項記載の液晶セル用シール剤組成物
(3) A patent claim in which the curing accelerator is a salt of 2,4,6 tri(dimethylaminomethyl)phenol and a compound having an ethylenic double bond and a -COOH group in the molecule. Sealant composition for liquid crystal cells according to scope 1
JP27333385A 1985-12-06 1985-12-06 Composition of sealing material for liquid crystal cell Pending JPS62133425A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP27333385A JPS62133425A (en) 1985-12-06 1985-12-06 Composition of sealing material for liquid crystal cell

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP27333385A JPS62133425A (en) 1985-12-06 1985-12-06 Composition of sealing material for liquid crystal cell

Publications (1)

Publication Number Publication Date
JPS62133425A true JPS62133425A (en) 1987-06-16

Family

ID=17526424

Family Applications (1)

Application Number Title Priority Date Filing Date
JP27333385A Pending JPS62133425A (en) 1985-12-06 1985-12-06 Composition of sealing material for liquid crystal cell

Country Status (1)

Country Link
JP (1) JPS62133425A (en)

Cited By (4)

* 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
WO2000017702A2 (en) 1998-09-21 2000-03-30 Gentex Corporation Improved seal for electrochromic devices
US6913798B2 (en) * 2000-06-21 2005-07-05 Mitsui Chemicals, Inc. Sealing material for plastic liquid crystal display cells including two-component epoxy resin composition
EP1666526A1 (en) * 2003-07-24 2006-06-07 Nitto Denko Corporation Inorganic powder-containing resin composition, film-forming material layer, transfer sheet, method for producing substrate with dielectric layer, and substrate with dielectric layer

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5690802A (en) * 1979-12-25 1981-07-23 Ube Ind Ltd Photocurable composition
JPS5758125A (en) * 1980-09-26 1982-04-07 Canon Inc Electrooptic device and its sealing method
JPS5868019A (en) * 1981-10-19 1983-04-22 Matsushita Electric Ind Co Ltd Cell for liquid crystal display element
JPS59232117A (en) * 1983-06-15 1984-12-26 Toray Chiokoole Kk Curing of epoxy resin

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5690802A (en) * 1979-12-25 1981-07-23 Ube Ind Ltd Photocurable composition
JPS5758125A (en) * 1980-09-26 1982-04-07 Canon Inc Electrooptic device and its sealing method
JPS5868019A (en) * 1981-10-19 1983-04-22 Matsushita Electric Ind Co Ltd Cell for liquid crystal display element
JPS59232117A (en) * 1983-06-15 1984-12-26 Toray Chiokoole Kk Curing of epoxy resin

Cited By (10)

* 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
WO2000017702A2 (en) 1998-09-21 2000-03-30 Gentex Corporation Improved seal for electrochromic devices
WO2000017702A3 (en) * 1998-09-21 2000-09-21 Gentex Corp Improved seal for electrochromic devices
US6157480A (en) * 1998-09-21 2000-12-05 Gentex Corporation Seal for electrochromic devices
US6195193B1 (en) 1998-09-21 2001-02-27 Gentex Corporation Seal for electrochromic devices
US6913798B2 (en) * 2000-06-21 2005-07-05 Mitsui Chemicals, Inc. Sealing material for plastic liquid crystal display cells including two-component epoxy resin composition
US7541075B2 (en) 2000-06-21 2009-06-02 Mitsui Chemicals, Inc. Sealant material for plastic liquid crystal display cells including one component epoxy resin composition
EP1666526A1 (en) * 2003-07-24 2006-06-07 Nitto Denko Corporation Inorganic powder-containing resin composition, film-forming material layer, transfer sheet, method for producing substrate with dielectric layer, and substrate with dielectric layer
EP1666526A4 (en) * 2003-07-24 2006-12-06 Nitto Denko Corp Inorganic powder-containing resin composition, film-forming material layer, transfer sheet, method for producing substrate with dielectric layer, and substrate with dielectric layer
US7585907B2 (en) 2003-07-24 2009-09-08 Nitto Denko Corporation Inorganic powder-containing resin composition, a film-forming material layer, a transfer sheet, method of producing a substrate having a dielectric layer formed thereon, and a substrate having a dielectric layer formed thereon

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