JP2000081701A5 - - Google Patents
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- JP2000081701A5 JP2000081701A5 JP1998249468A JP24946898A JP2000081701A5 JP 2000081701 A5 JP2000081701 A5 JP 2000081701A5 JP 1998249468 A JP1998249468 A JP 1998249468A JP 24946898 A JP24946898 A JP 24946898A JP 2000081701 A5 JP2000081701 A5 JP 2000081701A5
- Authority
- JP
- Japan
- Prior art keywords
- radiation
- protective film
- resin composition
- sensitive resin
- forming
- 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.)
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- 230000001681 protective Effects 0.000 claims description 15
- 239000011342 resin composition Substances 0.000 claims description 11
- 239000011248 coating agent Substances 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 230000001678 irradiating Effects 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000003505 polymerization initiator Substances 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000003700 epoxy group Chemical group 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- CNJRPYFBORAQAU-UHFFFAOYSA-N 1-Ethoxy-2-(2-Methoxyethoxy)Ethane Chemical compound CCOCCOCCOC CNJRPYFBORAQAU-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N Glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
Description
【０００１】
【発明の属する技術分野】
本発明は、液晶表示装置用のカラーフィルター保護膜として好適な感放射線性樹脂組成物保護膜およびその形成方法に関する。特にギャップ制御用柱状スペーサーを有する保護膜を形成するのに好適な感放射線性樹脂組成物保護膜およびその形成方法に関する。
[0001]
[Technical field to which the invention belongs]
The present invention relates to a radiation-sensitive resin composition protective film suitable as a color filter protective film for a liquid crystal display device and a method for forming the same. In particular, the present invention relates to a radiation-sensitive resin composition protective film suitable for forming a protective film having a columnar spacer for gap control, and a method for forming the protective film.
【０００７】
【発明が解決しようとする課題】
それ故、本発明の目的は、ラビングにより表示不良が生じないようラビング耐性が高く、さらに、熱により形状が変化しないよう耐熱寸法安定性が高くそして、液晶パネルにかかる外部圧力により形状が変化しないよう圧縮強度が高い、ギャップ制御用柱状スペーサーを有する保護膜を形成するのに好適な感放射線性樹脂組成物を提供することにある。
本発明の他の目的は、本発明の感放射線性樹脂組成物から保護膜を形成する方法および形成された保護膜を提供することにある。
本発明の他の目的および利点は以下の説明から明らかになろう。
0007
[Problems to be Solved by the Invention]
Therefore, an object of the present invention is that the rubbing resistance is high so that display defects do not occur due to rubbing, the heat-resistant dimensional stability is high so that the shape does not change due to heat, and the shape does not change due to external pressure applied to the liquid crystal panel. It is an object of the present invention to provide a radiation-sensitive resin composition suitable for forming a protective film having a columnar spacer for controlling a gap, which has a high compressive strength.
Another object of the present invention is to provide a method for forming a protective film from the radiation-sensitive resin composition of the present invention and the formed protective film.
Other objects and advantages of the present invention will become apparent from the following description.
本発明によれば、本発明の上記目的および利点は、第２に、
以下の工程を以下に記載順で実施することを特徴とする保護膜の形成方法によって達成される。
（１）本発明の感放射線性樹脂組成物の塗膜を基板上に形成する工程、
（２）該塗膜に所定のマスクを介して放射線を照射する工程、
（３）現像工程、
（４）該現像後の膜の全面に放射線を照射する工程、および
（５）加熱工程。
本発明によれば、本発明の上記目的および利点は、第３に、
本発明の感放射線性樹脂組成物から形成された保護膜によって達成される。
以下、本発明のカラーフィルター保護膜用感放射線性樹脂組成物について詳述する。
本発明のカラーフィルター保護膜用感放射線性樹脂組成物は、上記のとおり、共重合体［Ａ］、重合性化合物［Ｂ］および重合開始剤［Ｃ］からなることを特徴とする。
According to the present invention, the above object and advantage of the present invention are secondly:
It is achieved by a method for forming a protective film, which comprises carrying out the following steps in the order described below.
(1) A step of forming a coating film of the radiation-sensitive resin composition of the present invention on a substrate,
(2) A step of irradiating the coating film with radiation through a predetermined mask.
(3) Development process,
(4) A step of irradiating the entire surface of the developed film with radiation, and
(5) Heating step.
According to the present invention, the above object and advantage of the present invention are, thirdly,
This is achieved by a protective film formed from the radiation-sensitive resin composition of the present invention.
Hereinafter, the radiation-sensitive resin composition for a color filter protective film of the present invention will be described in detail.
As described above, the radiation-sensitive resin composition for a color filter protective film of the present invention is characterized by comprising a copolymer [A], a polymerizable compound [B], and a polymerization initiator [C].
合成例１
冷却管、撹拌機を備えたフラスコに、２,２’−アゾビス（２,４−ジメチルバレロニトリル）７重量部およびジエチレングリコールメチルエチルエーテル２００重量部を仕込んだ。引き続きスチレン２５重量部、メタクリル酸１０重量部、メタクリル酸ジシクロペンタニル２０重量部およびメタクリル酸グリシジル４５重量部を仕込み窒素置換した後、ゆるやかに攪拌を始めた。溶液の温度を７０℃に上昇させ、この温度を５時間保持し共重合体［Ａ−１］を含む重合体溶液を得た。得られた重合体溶液の固形分濃度は３３.０重量％であり、重合体の重量平均分子量は、２４,０００であった（重量平均分子量はＧＰＣ（ゲルパーミエイションクロマトグラフィー） ＨＬＣ−８０２０（東ソー（株）製）を用いて測定したポリスチレン換算分子量である）。
Synthesis example 1
A flask equipped with a cooling tube and a stirrer was charged with 7 parts by weight of 2,2'-azobis (2,4-dimethylvaleronitrile) and 200 parts by weight of diethylene glycol methyl ethyl ether. Subsequently, 25 parts by weight of styrene, 10 parts by weight of methacrylic acid, 20 parts by weight of dicyclopentanyl methacrylate and 45 parts by weight of glycidyl methacrylate were charged and replaced with nitrogen, and then gentle stirring was started. The temperature of the solution was raised to 70 ° C., and this temperature was maintained for 5 hours to obtain a polymer solution containing the copolymer [A-1]. The solid content concentration of the obtained polymer solution was 33.0% by weight, and the weight average molecular weight of the polymer was 24,000 (the weight average molecular weight was GPC (gel permeation chromatography) HLC-8020. (Polystyrene-equivalent molecular weight measured using Tosoh Corporation).
Claims (3)
（ａ２）エポキシ基含有不飽和化合物、および
（ａ３）前記（ａ１）および（ａ２）以外のオレフィン系不飽和化合物、
の共重合体、
［Ｂ］エチレン性不飽和結合を有する重合性化合物、並びに
［Ｃ］感放射線重合開始剤
を含有することを特徴とするカラーフィルター保護膜用感放射線性樹脂組成物。[A] (a1) unsaturated carboxylic acid and / or unsaturated carboxylic acid anhydride,
(A2) an epoxy group-containing unsaturated compound, and (a3) an olefinically unsaturated compound other than (a1) and (a2),
A copolymer of
[B] A radiation-sensitive resin composition for a color filter protective film, comprising a polymerizable compound having an ethylenically unsaturated bond, and [C] a radiation-sensitive polymerization initiator.
（１）請求項１に記載の感放射線性樹脂組成物の塗膜を基板上に形成する工程、(1) The process of forming the coating film of the radiation sensitive resin composition of Claim 1 on a board | substrate,
（２）該塗膜に所定のマスクを介して放射線を照射する工程、(2) A step of irradiating the coating film with radiation through a predetermined mask;
（３）現像工程、(3) Development process,
（４）該現像後の膜の全面に放射線を照射する工程、および(4) a step of irradiating the entire surface of the developed film with radiation, and
（５）加熱工程。(5) Heating step.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24946898A JP2000081701A (en) | 1998-09-03 | 1998-09-03 | Radiation sensitive resin composition for protective coat of color filter |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24946898A JP2000081701A (en) | 1998-09-03 | 1998-09-03 | Radiation sensitive resin composition for protective coat of color filter |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2000081701A JP2000081701A (en) | 2000-03-21 |
| JP2000081701A5 true JP2000081701A5 (en) | 2005-06-30 |
Family
ID=17193416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24946898A Pending JP2000081701A (en) | 1998-09-03 | 1998-09-03 | Radiation sensitive resin composition for protective coat of color filter |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2000081701A (en) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001222107A (en) * | 2000-02-10 | 2001-08-17 | Dainippon Printing Co Ltd | Photosensitive resin composition for forming pattern, and color filter |
| JP2002303976A (en) * | 2001-04-04 | 2002-10-18 | Jsr Corp | Radiation sensitive composition, spacer and color liquid crystal display |
| KR101084384B1 (en) * | 2004-05-06 | 2011-11-18 | 제이에스알 가부시끼가이샤 | Radiation-sensitive resin composition, spacer, and method of forming the same |
| JP4531511B2 (en) * | 2004-09-30 | 2010-08-25 | 大日本印刷株式会社 | Manufacturing method of color filter |
| JP4736679B2 (en) * | 2005-09-29 | 2011-07-27 | 大日本印刷株式会社 | Cured film for liquid crystal display |
| JP4650630B2 (en) * | 2005-10-07 | 2011-03-16 | Ｊｓｒ株式会社 | Radiation sensitive resin composition for spacer, spacer, and formation method thereof |
| JP4774908B2 (en) * | 2005-10-20 | 2011-09-21 | 凸版印刷株式会社 | Color filter for liquid crystal display device and liquid crystal display device |
| JP4899414B2 (en) * | 2005-10-25 | 2012-03-21 | 凸版印刷株式会社 | Manufacturing method of color filter for liquid crystal display device |
| JP4818839B2 (en) * | 2006-07-19 | 2011-11-16 | 株式会社 日立ディスプレイズ | Liquid crystal display device and manufacturing method thereof |
| JP4978128B2 (en) * | 2006-09-22 | 2012-07-18 | 大日本印刷株式会社 | Photocurable resin composition |
| US20110123929A1 (en) | 2007-01-23 | 2011-05-26 | Fujifilm Corporation | Oxime compound, photosensitive composition, color filter, production method for the color filter, and liquid crystal display element |
| EP2144900B1 (en) | 2007-05-11 | 2015-03-18 | Basf Se | Oxime ester photoinitiators |
| EP2144876B1 (en) | 2007-05-11 | 2012-09-12 | Basf Se | Oxime ester photoinitiators |
| CN102361896B (en) | 2009-03-23 | 2015-10-07 | 巴斯夫欧洲公司 | Photo-corrosion-resisting agent composition |
| US9051397B2 (en) | 2010-10-05 | 2015-06-09 | Basf Se | Oxime ester |
| KR101831912B1 (en) | 2010-10-05 | 2018-02-26 | 바스프 에스이 | Oxime ester derivatives of benzocarbazole compounds and their use as photoinitiators in photopolymerizable compositions |
| WO2012101245A1 (en) | 2011-01-28 | 2012-08-02 | Basf Se | Polymerizable composition comprising an oxime sulfonate as thermal curing agent |
| JP5992930B2 (en) | 2011-02-23 | 2016-09-14 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Sulfonium sulfate and its manufacture and use |
| EP2788325B1 (en) | 2011-12-07 | 2016-08-10 | Basf Se | Oxime ester photoinitiators |
| US9631048B2 (en) | 2012-04-19 | 2017-04-25 | Basf Se | Sulfonium compounds, their preparation and use |
| JP6095771B2 (en) | 2012-05-09 | 2017-03-15 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Oxime ester photoinitiator |
| US10234761B2 (en) | 2013-07-08 | 2019-03-19 | Basf Se | Oxime ester photoinitiators |
| EP3044208B1 (en) | 2013-09-10 | 2021-12-22 | Basf Se | Oxime ester photoinitiators |
| KR20170048422A (en) | 2014-08-29 | 2017-05-08 | 바스프 에스이 | Oxime sulfonate derivatives |
| US9994538B2 (en) | 2015-02-02 | 2018-06-12 | Basf Se | Latent acids and their use |
| US20220121113A1 (en) | 2019-01-23 | 2022-04-21 | Basf Se | Oxime ester photoinitiators having a special aroyl chromophore |
| JP2023517304A (en) | 2020-03-04 | 2023-04-25 | ベーアーエスエフ・エスエー | oxime ester photoinitiator |
-
1998
- 1998-09-03 JP JP24946898A patent/JP2000081701A/en active Pending
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