JPH03179401A - Surface protective material - Google Patents

Surface protective material

Info

Publication number
JPH03179401A
JPH03179401A JP1319474A JP31947489A JPH03179401A JP H03179401 A JPH03179401 A JP H03179401A JP 1319474 A JP1319474 A JP 1319474A JP 31947489 A JP31947489 A JP 31947489A JP H03179401 A JPH03179401 A JP H03179401A
Authority
JP
Japan
Prior art keywords
group
denotes
surface protective
functional group
integer
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
JP1319474A
Other languages
Japanese (ja)
Inventor
Hidehiko Matsuka
松家 英彦
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.)
Sanyo Chemical Industries Ltd
Original Assignee
Sanyo Chemical Industries 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 Sanyo Chemical Industries Ltd filed Critical Sanyo Chemical Industries Ltd
Priority to JP1319474A priority Critical patent/JPH03179401A/en
Publication of JPH03179401A publication Critical patent/JPH03179401A/en
Pending legal-status Critical Current

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  • Optical Filters (AREA)
  • Liquid Crystal (AREA)
  • Surface Treatment Of Optical Elements (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

PURPOSE:To flatten the picture element patterns of color filters by constituting the surface protective material of a specific org. high polymer contg. styrene and photodimerization type functional group. CONSTITUTION:This surface protective material consists of the org. high polymer which has the unit of the styrene and the unit contg. the functional group of the photodimerization type, is expressed by formula I and has 500 to 10,000 weight average mol. wt. In the formula, R1 and R2 denote a hydrogen atom, methyl group; R3 denotes a monovalent org. group contg. the functional group of the photodimerization type; Ar denotes a phenyl group or naphthyl group; (m) denotes 0, 1 integer; (n) denotes >=1 integer. Thus, the ideally flat surface protective layer is applied on the color filters and further heat resistance, chemical resistance and transparency are obtd.

Description

【発明の詳細な説明】 [産業上の利用分野] 本発明は、液晶表示素子またはCCD (チャージカプ
ルドデバイス)、BBD(パケットブリケートデバイス
)、CID(チャージインジェクションデバイス)等か
らなる固体撮像素子等のカラーフィルターの表面保護材
料に関する6[従来の技術] 従来、液晶表示ζ子や固体撮像素子のカラーフィルター
の製造において、カラーフィルターの表面保護材料とし
て可視光領域に高い光透過性を有する熱硬化型のアクリ
ル樹脂(例えば、オプトマーSS、日本合成ゴム製など
)が知られている(特開昭61−292604号)。
[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a solid-state image sensor consisting of a liquid crystal display element, a CCD (charge coupled device), a BBD (packet coupled device), a CID (charge injection device), etc. 6 [Prior art] Regarding surface protection materials for color filters such as Curable acrylic resins (for example, Optomer SS, manufactured by Japan Synthetic Rubber, etc.) are known (Japanese Patent Application Laid-Open No. 61-292604).

[発明が解決しようとする課題] ところが、最近の液晶表示素子や固体撮像素子の高解像
度化に対応して、カラーフィルター表面の平坦性が要求
されてきており、該熱硬化型アクリル樹脂では、カラー
フィルターの画素パターンを平坦化できないという問題
点があった。
[Problems to be Solved by the Invention] However, in response to the recent increase in resolution of liquid crystal display elements and solid-state image sensors, flatness of the color filter surface has been required, and the thermosetting acrylic resin has There was a problem in that the pixel pattern of the color filter could not be flattened.

[課題を解決するための手段] 本発明者らは、液晶表示素子や固体撮像素子の高解像度
化を可能とする理想的な平坦性を有するカラーフィルタ
ーの表面保護材料について鋭意検討した結果、本発明に
達した。
[Means for Solving the Problems] The present inventors have conducted extensive studies on surface protection materials for color filters that have ideal flatness that enables high resolution of liquid crystal display elements and solid-state image sensors, and have developed the present invention. Achieved invention.

すなはち本発明は、 スチレンまたはスチレン誘導体の単位と側鎖に光二量化
型および/または光重合型の官能基を含有する単位を有
する一般式(1): 明m書の浄書(内容に変更なし) (式中、R+およびR2は、水素原子またはメチル基、
Rsは、光二量化型および/または光重合型の官能基を
含有する一価の有機基、Arは、フェニル基またはナフ
チル基、mは、Oまたは1以上の整数、nは、 1以上
の整数。) で示される重量平均分子量が500〜10000の有機
高分子すらなることを特徴とする表面保護材料である。
In other words, the present invention provides general formula (1) having a unit of styrene or a styrene derivative and a unit containing a photodimerizable and/or photopolymerizable functional group in the side chain: None) (wherein R+ and R2 are a hydrogen atom or a methyl group,
Rs is a monovalent organic group containing a photodimerizable and/or photopolymerizable functional group, Ar is a phenyl group or a naphthyl group, m is O or an integer of 1 or more, and n is an integer of 1 or more. . ) It is a surface protection material characterized by comprising an organic polymer having a weight average molecular weight of 500 to 10,000.

一般式(1)において、Raの光二量化型官能基を含有
する一価の有機基としては、 明#i書の浄書(内容に変更なし) などのケイ皮酸含有基、 一〇〇〇C112ClI2 ococu=ca−co:
cH@−C[120COfJ=fl:H−(H=CH@
などのシンナミリデン酢酸含有基、 −Go−C■=cn@ 、 −coo@an:aトco@ などのスチリルケトン含有基、 などのスチルベン含有基、 明細書の浄書(内容に変更なし) などのα−フェニル含有基、 などのベンゾフェノン含有基などが挙げられる。
In the general formula (1), the monovalent organic group containing a photodimerizable functional group of Ra is a cinnamic acid-containing group such as the engraving of Ming #i (no change in content), 1000C112ClI2 ococu=ca-co:
cH@-C[120COfJ=fl:H-(H=CH@
Cinnamylidene acetic acid-containing groups such as -Go-C■=cn@, styryl ketone-containing groups such as -coo@an:atoco@, stilbene-containing groups such as, engraving of the specification (no change in content), etc. Examples include α-phenyl-containing groups and benzophenone-containing groups such as .

Rsの光重合型官能基を含有する一価の有機基としては
、 −COOCH2CH=CHt、 などのビニル含有基、 一0O0CII*CH20COCR:(R2、−COO
CIhC11*0COC((Ha)C:CH2、CHa
OCOCR=CH2, 0CONHCH2CH20COC■=CH2、明細書の
浄側内容に変更なし) などのアクリル酸またはメタクリル酸含有基などが挙げ
られる。
Monovalent organic groups containing a photopolymerizable functional group of Rs include vinyl-containing groups such as -COOCH2CH=CHt, 10O0CII*CH20COCR: (R2, -COO
CIhC11*0COC((Ha)C:CH2, CHa
Examples include acrylic acid- or methacrylic acid-containing groups such as OCOCR=CH2, 0CONHCH2CH20COC=CH2 (no change to the content of the specification).

R3の好ましいものは、 である。Preferred R3 are: It is.

rrh  nについては、通常mは、O〜90tnは、
1〜50であり、好ましくは、mは、0〜601nは、
 20〜50である。
For rrh n, normally m is O~90tn,
1 to 50, preferably m is 0 to 601n,
It is 20-50.

mとnの比は、通常、O:100〜θO: 10、であ
り、好ましくは、o:ioo〜70:  30である。
The ratio of m and n is usually O:100 to θO:10, preferably o:ioo to 70:30.

nの比率が、10未満であれば、光硬化時の架橋密度が
少なく、耐熱性、耐薬品性が不充分となる。
If the ratio of n is less than 10, the crosslinking density during photocuring will be low, resulting in insufficient heat resistance and chemical resistance.

明細書の浄書(内容に変更なし) 分子量は、通常500〜tooooであり、好ましくは
、2000〜80ooである。重量平均分子量が、50
0未満であれば、光硬化物の耐熱性、耐薬品性が不充分
となる。また、重量平均分子量が10000を越えると
加熱時の有機高分子の溶融レベリング性が不十分となり
、理想的な平坦面が得られにくくなる。
Copying of the specification (no change in content) The molecular weight is usually 500-toooo, preferably 2000-80oo. Weight average molecular weight is 50
If it is less than 0, the heat resistance and chemical resistance of the photocured product will be insufficient. Furthermore, if the weight average molecular weight exceeds 10,000, the melt leveling properties of the organic polymer during heating will be insufficient, making it difficult to obtain an ideal flat surface.

一般式(1)で示される有機高分子の具体例としては、 (有機高分子1)重量平均分子量5000m:n=50
:50 (有機高分子2)重量平均分子量・8000m:  n
=60:  40 (有機高分子3) 重量平均分子!昶oo。
Specific examples of organic polymers represented by general formula (1) include (Organic polymer 1) Weight average molecular weight 5000m: n=50
:50 (Organic polymer 2) Weight average molecular weight・8000m: n
=60: 40 (Organic polymer 3) Weight average molecule!昶oo.

(有機高分子4)重量平均分子量7000m: n=1
0: 90 などが挙げられる。
(Organic polymer 4) Weight average molecular weight 7000m: n=1
Examples include 0:90.

一般式(1)で示される有機高分子の合成法としては、
BFs−E t*o1A I C1*s  T i C
1a、などのルイス酸やH*SOa、HCl0a、CF
参〇00H,p−)ルエンスルホン酸などのプロトン酸
によるカチオン重合法、ブチルリチウム、ナトリウム−
ナフタレン錯体などによるアニオン重合法、ベンゾイル
パーオキサイド、ジクミルノf−オキサイド、アゾビス
イソブチロニトリルなどのラジカル重合法または、高分
子反応法などがある。
As a method for synthesizing the organic polymer represented by general formula (1),
BFs-E t*o1A I C1*s T i C
Lewis acids such as 1a, H*SOa, HCl0a, CF
〇00H, p-) Cationic polymerization method using protic acids such as luenesulfonic acid, butyllithium, sodium-
Examples include an anionic polymerization method using a naphthalene complex, a radical polymerization method using benzoyl peroxide, dicumyl f-oxide, azobisisobutyronitrile, etc., and a polymer reaction method.

本発明の表面保護材料は、一般式(1)で示される有機
高分子を芳香族炭化水素(トルエン、キシレンなど)、
エステル化合物(酢酸エチルセロソルブなど)などに溶
解して使用状態になるiこの場合の固形物濃度はM量基
準で10〜60%である。
The surface protection material of the present invention combines the organic polymer represented by the general formula (1) with aromatic hydrocarbons (toluene, xylene, etc.),
It is dissolved in an ester compound (ethyl cellosolve acetate, etc.) and ready for use. In this case, the solid concentration is 10 to 60% based on the amount of M.

本発明の表面保護材料の使用方法は、RGBの三色のカ
ラーフィルターのパターンを有するガラス基板上に一般
式(1)で示される有機高分子をスピン塗布、スプレー
塗布、ロールコート塗布、デイピング塗布、印刷塗布な
どにより膜厚0.5〜10μmとなるように塗布する。
The method of using the surface protection material of the present invention includes spin coating, spray coating, roll coating, or dipping coating of an organic polymer represented by the general formula (1) on a glass substrate having a pattern of RGB three-color color filters. The coating is applied by printing or the like to a thickness of 0.5 to 10 μm.

続いて、該有機高分子膜を赤外ランプ、ホットプレート
、クリーンオーブンなどにより100〜250℃で加熱
し、溶融流動させ平坦化面を得た後、該有機高分子膜の
耐熱性を向上させるために紫外線ランプまたは、遠紫外
線ランプで硬化させることによりカラーフィルター上に
理想的に平坦な表面保護膜が形成できる。
Subsequently, the organic polymer film is heated at 100 to 250°C using an infrared lamp, hot plate, clean oven, etc. to melt and flow it to obtain a flattened surface, and then improve the heat resistance of the organic polymer film. Therefore, by curing with an ultraviolet lamp or deep ultraviolet lamp, an ideally flat surface protective film can be formed on the color filter.

[実施例] 以下、実施例により本発明を更に具体的に説明するが1
本発明の範囲はこれらの実施例によって限定されるもの
ではない。
[Example] Hereinafter, the present invention will be explained in more detail with reference to Examples.
The scope of the invention is not limited by these examples.

実施例1 有機高分子1を10g、キシレンを40gを混合しこれ
を孔径0.2μmのフィルターで濾過した後、以ドの表
面保護材料用の組成物とした。
Example 1 10 g of Organic Polymer 1 and 40 g of xylene were mixed and filtered through a filter with a pore size of 0.2 μm to prepare a composition for the following surface protection material.

第1図に示すように、3μmの厚さを有するRGBのカ
ラーフィルターパターンを有するガラス基板上に上記表
面保護材料用組成物の溶液を3000回転で全面に回転
塗布した。塗布膜厚は、3μmであった。(第2図) 次に、150°Cで5分間加熱処理を行い(第3図)、
続いて高圧水銀灯により紫外線を1分間照射し硬化を行
った。(第4図) その結果、0.1μm以下に平坦化された表面保護膜層
が得られた。
As shown in FIG. 1, a solution of the above-mentioned surface protection material composition was spin-coated on the entire surface of a glass substrate having an RGB color filter pattern having a thickness of 3 μm at 3000 revolutions. The coating film thickness was 3 μm. (Figure 2) Next, heat treatment was performed at 150°C for 5 minutes (Figure 3).
Subsequently, ultraviolet rays were irradiated for 1 minute using a high-pressure mercury lamp to effect curing. (FIG. 4) As a result, a surface protective film layer flattened to 0.1 μm or less was obtained.

また、この1摸は、可視光(400〜800 n m 
)の透過率が、98.0%以上で良好な透明性を示した
In addition, this one sample uses visible light (400 to 800 nm
) had a transmittance of 98.0% or more, indicating good transparency.

さらに、IT○蒸着の加熱時にグラツク、着色等がなく
、ざらにITOエツチング時や配向膜塗布時に膜の膨潤
や溶解等がなく良好な耐熱性、耐薬品性を示した。
Furthermore, there was no cracking or coloring during heating during IT○ vapor deposition, and there was no swelling or dissolution of the film during ITO etching or alignment film application, showing good heat resistance and chemical resistance.

[発明の効果] 本発明の表面保護材料は、カラーフィルター上に理想的
に平坦性な表面保護層を与え、さらに耐熱性、耐薬品性
また透明性とも良好であった。
[Effects of the Invention] The surface protection material of the present invention provided an ideally flat surface protection layer on a color filter, and also had good heat resistance, chemical resistance, and transparency.

これは、液晶表示素子や固体撮像素子の高解像化に充分
対応できるものである。
This can sufficiently correspond to higher resolution of liquid crystal display elements and solid-state image sensors.

【図面の簡単な説明】[Brief explanation of drawings]

第工〜4図は、本発明の表面保護材料の使用方法の説明
図(断面図)である。 1・・カラーフィルター 2・・ガラス基板 3・・塗布された表面保護材料 4・・加熱によりレベリングした表面保護材料1 ・紫外線硬化した表面保護材料
Figures 1 to 4 are explanatory diagrams (cross-sectional views) of the method of using the surface protection material of the present invention. 1. Color filter 2. Glass substrate 3. Coated surface protection material 4. Surface protection material leveled by heating 1. Surface protection material cured by ultraviolet rays.

Claims (1)

【特許請求の範囲】 1 スチレンまたはスチレン誘導体の単位と側鎖に光二
量化型および/または光重合型の官能基を含有する単位
を有する一般式(1): ▲数式、化学式、表等があります▼(1) (式中、R_1およびR_2は、水素原子またはメチル
基、R_3は、光二量化型および/または光重合型の官
能基を含有する一価の有機基、Arは、フェニル基また
はナフチル基、mは、0または1以上の整数、nは、1
以上の整数、) で示される重量平均分子量が500〜10000の有機
高分子からなることを特徴とする表面保護材料。
[Claims] 1 General formula (1) having a unit of styrene or a styrene derivative and a unit containing a photodimerizable and/or photopolymerizable functional group in the side chain: ▲ Includes mathematical formulas, chemical formulas, tables, etc. ▼(1) (In the formula, R_1 and R_2 are hydrogen atoms or methyl groups, R_3 is a monovalent organic group containing a photodimerizable and/or photopolymerizable functional group, and Ar is a phenyl group or naphthyl group. group, m is an integer of 0 or 1 or more, n is 1
A surface protection material comprising an organic polymer having a weight average molecular weight of 500 to 10,000 represented by the following integer.
JP1319474A 1989-12-08 1989-12-08 Surface protective material Pending JPH03179401A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP1319474A JPH03179401A (en) 1989-12-08 1989-12-08 Surface protective material

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP1319474A JPH03179401A (en) 1989-12-08 1989-12-08 Surface protective material

Publications (1)

Publication Number Publication Date
JPH03179401A true JPH03179401A (en) 1991-08-05

Family

ID=18110604

Family Applications (1)

Application Number Title Priority Date Filing Date
JP1319474A Pending JPH03179401A (en) 1989-12-08 1989-12-08 Surface protective material

Country Status (1)

Country Link
JP (1) JPH03179401A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160037867A (en) 2016-03-22 2016-04-06 주식회사 포스코 HOT DIP Zn ALLOY PLATED STEEL SHEET HAVING EXCELLENT ANTI-CORROSION AND METHOD FOR MANUFACTURING THE STEEL SHEET USING THE SAME

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4915501A (en) * 1972-06-02 1974-02-12

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4915501A (en) * 1972-06-02 1974-02-12

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160037867A (en) 2016-03-22 2016-04-06 주식회사 포스코 HOT DIP Zn ALLOY PLATED STEEL SHEET HAVING EXCELLENT ANTI-CORROSION AND METHOD FOR MANUFACTURING THE STEEL SHEET USING THE SAME

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