JPH0253778B2 - - Google Patents

Info

Publication number
JPH0253778B2
JPH0253778B2 JP58140907A JP14090783A JPH0253778B2 JP H0253778 B2 JPH0253778 B2 JP H0253778B2 JP 58140907 A JP58140907 A JP 58140907A JP 14090783 A JP14090783 A JP 14090783A JP H0253778 B2 JPH0253778 B2 JP H0253778B2
Authority
JP
Japan
Prior art keywords
weight
photosensitive
developer
present
polyvinyl formal
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.)
Expired - Lifetime
Application number
JP58140907A
Other languages
Japanese (ja)
Other versions
JPS59187340A (en
Inventor
Takeo Morya
Toshio Yamagata
Masako Ogura
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.)
Kimoto Co Ltd
Original Assignee
Kimoto 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 Kimoto Co Ltd filed Critical Kimoto Co Ltd
Priority to JP14090783A priority Critical patent/JPS59187340A/en
Publication of JPS59187340A publication Critical patent/JPS59187340A/en
Publication of JPH0253778B2 publication Critical patent/JPH0253778B2/ja
Granted legal-status Critical Current

Links

Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/022Quinonediazides
    • G03F7/023Macromolecular quinonediazides; Macromolecular additives, e.g. binders
    • G03F7/0233Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides

Landscapes

  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)

Description

【発明の詳細な説明】 [産業上の利用分野] 本発明はポリビニルホルマールと、オルソキノ
ンジアジド系化合物とを含有する感光性組成物に
関するものであり、さらに詳細には感光被膜が強
靭で水系現像液で現像可能な感光性組成物に関す
るものである。
Detailed Description of the Invention [Industrial Field of Application] The present invention relates to a photosensitive composition containing polyvinyl formal and an orthoquinone diazide compound, and more particularly to a photosensitive composition that has a strong photosensitive coating and is compatible with an aqueous developer. The present invention relates to a photosensitive composition that can be developed with.

[従来の技術及び発明が解決しようとする課題] 従来より高分子化合物とオルソキノンジアジド
系化合物とを含有する感光性組成物が知られてお
り、例えばフエノール樹脂と、1、2−ナフトキ
ノン−ジアジド(2)−4−スルホン酸のノボラツク
エステルの組合せがある。これらはフオトレジス
ト、フオトレリーフなどの用途に利用されてい
る。しかしながら、これらの組合せではアルカリ
水溶液で現像可能であるが、感光皮膜が脆く、き
ずがつきやすいなど機械的強度が不十分である。
[Prior Art and Problems to be Solved by the Invention] Photosensitive compositions containing a polymer compound and an orthoquinone diazide compound have been known, for example, a phenol resin and a 1,2-naphthoquinone diazide ( 2) There is a combination of novolac esters of -4-sulfonic acid. These are used for applications such as photoresist and photorelief. However, although these combinations can be developed with an alkaline aqueous solution, the photosensitive film is brittle and easily scratched, resulting in insufficient mechanical strength.

[発明の目的] 本発明の目的は、これらの問題点を解消し、感
光皮膜が強靭でしかも水系現液で現像可能な感光
性組成物を提供することにある。
[Object of the Invention] An object of the present invention is to solve these problems and provide a photosensitive composition which has a tough photosensitive film and can be developed with an aqueous developer.

[課題を解決するための手段] 本発明者は、前記の問題点を解決すべく鋭意研
究を進めた結果、ポリビニルホルマール、オルソ
キノンジアジド系化合物とを含有する感光性組成
物を使用するときは前記目的を達成し得ることを
発見した。本発明はかかる知見に基づいてなされ
たものである。
[Means for Solving the Problems] As a result of intensive research to solve the above-mentioned problems, the present inventors have found that when using a photosensitive composition containing polyvinyl formal and orthoquinonediazide-based compounds, the above-mentioned I discovered that I could achieve my goal. The present invention has been made based on this knowledge.

本発明において使用する高分子化合物としての
ポリビニルホルマールは有機溶剤に可溶であれば
使用可能であるが、その分子量が少なすぎると皮
膜強度が低下し、又、分子量が大きすぎると感光
液が高粘度になり、その調整が困難になるため好
ましくない。ホルマール化度については低くすぎ
ると耐水性が悪くなり、高すぎると水系現像液で
の現像性が低下する。以下の理由によりポリビニ
ルホルマールは、平均分子量9000から150000でホ
ルマール化度が20から80mol%のものが好まし
い。
Polyvinyl formal as a polymer compound used in the present invention can be used as long as it is soluble in an organic solvent, but if its molecular weight is too small, the film strength will decrease, and if its molecular weight is too large, the photosensitive solution will become too high. This is not preferable because it becomes viscous and difficult to adjust. If the degree of formalization is too low, water resistance will deteriorate, and if it is too high, developability with an aqueous developer will decrease. For the following reasons, the polyvinyl formal preferably has an average molecular weight of 9,000 to 150,000 and a degree of formalization of 20 to 80 mol%.

又、本発明において使用するオルソキノンジア
ジド系化合物としては、2−ジアゾ−1−ナフト
ール−5(4′−メチルフエニルスルホネート)、2
−ジアゾ−1−ナフトール−5−フエノキシスル
ホネート、1、2−ナフトキノン−ジアジド(2)−
4−スルホン酸のノボラツクエステル、2、2′−
ジヒドロキシ−ジフエニル−ビス−(ナフトキノ
ン−1、2−ジアジド−5−スルホン酸エステ
ル)、2、3、4−トリオキシベンザフエノン−
ビス−(ナフトキノン−1、2−ジアジド−5−
スルホン酸エステル)等をあげることができる。
In addition, the orthoquinonediazide compounds used in the present invention include 2-diazo-1-naphthol-5(4'-methylphenylsulfonate), 2-diazo-1-naphthol-5(4'-methylphenylsulfonate),
-Diazo-1-naphthol-5-phenoxysulfonate, 1,2-naphthoquinone-diazide (2)-
Novolac ester of 4-sulfonic acid, 2,2'-
Dihydroxy-diphenyl-bis-(naphthoquinone-1,2-diazide-5-sulfonic acid ester), 2,3,4-trioxybenzaphenone-
Bis-(naphthoquinone-1,2-diazide-5-
sulfonic acid esters), etc.

これらオルソキノンジアジド系化合物の、高分
子化合物に対する添加量は、重量で通常5から50
%、好適な添加量は10から30%である。
The amount of these orthoquinone diazide compounds added to the polymer compound is usually 5 to 50% by weight.
%, the preferred addition amount is 10 to 30%.

さらに、必要に応じ、染料、顔料等を添加して
も差支えない。又、使用目的に応じ、現像性、耐
触性等の改善の必要が有れば、ポリビニルホルマ
ールと相溶性のあるフエノール樹脂、スチレン−
マレイン酸共重合樹脂、アルキツド樹脂、エポキ
シ樹脂等をポリビニルホルマールに対して等量ま
で添加しても良い。
Furthermore, if necessary, dyes, pigments, etc. may be added. Depending on the purpose of use, if there is a need to improve developability, contact resistance, etc., phenolic resins and styrene resins that are compatible with polyvinyl formal may be used.
Maleic acid copolymer resin, alkyd resin, epoxy resin, etc. may be added in an equal amount to polyvinyl formal.

本発明の感光性組成物は、一般的には有機溶剤
に溶解し、基材に塗布して使用する。有機溶剤の
具体例としては、アセトン、メチルエチルケト
ン、シクロヘキサノン、メチルアルコール、エチ
ルアルコール、プロピルアルコール、トルエン、
キシレン、酢酸エチル、酢酸ブチル、エチレング
リコールモノメチルエーテル、エチレングリコー
ルモノエチルエーテル、ジメチルホルムアミド
等、又はこれら有機溶剤の混合物をあげることが
できる。
The photosensitive composition of the present invention is generally used by dissolving it in an organic solvent and applying it to a substrate. Specific examples of organic solvents include acetone, methyl ethyl ketone, cyclohexanone, methyl alcohol, ethyl alcohol, propyl alcohol, toluene,
Examples include xylene, ethyl acetate, butyl acetate, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, dimethylformamide, and mixtures of these organic solvents.

本発明の感光性組成物の現像液としては、芳香
族カルボン酸、芳香族スルホン酸、フエノール
類、又はアルキル硫酸のアルカリ金属塩化合物
と、アルカリ金属の水酸化合物及びあるいは炭酸
塩との水溶液を使用することができる。これらの
化合物の具体例を示せば、芳香族カルボン酸とし
てはP−クロル安息香酸、サリチル酸、アントラ
ニル酸等、芳香族スルホン酸としては1−ナフト
ール−4−スルホン酸等、フエノール類としては
P−ヒドロキシ安息香酸エチル、ペンタクロルフ
エノール等、アルキル硫酸としてはラウリル硫酸
等のナトリウム、カリウム等のアルカリ金属塩化
合物をあげることができる。また、これらのアル
カリ金属の水酸化物あるいは炭酸塩の具体例を示
せば、前者としては、水酸化ナトリウム、水酸化
カリウム、後者としては炭酸ナトリウム、炭酸カ
リウムがある。
As the developer for the photosensitive composition of the present invention, an aqueous solution of an alkali metal salt compound of aromatic carboxylic acid, aromatic sulfonic acid, phenols, or alkyl sulfuric acid, and an alkali metal hydroxide compound and/or carbonate is used. can be used. Specific examples of these compounds include aromatic carboxylic acids such as P-chlorobenzoic acid, salicylic acid, and anthranilic acid, aromatic sulfonic acids such as 1-naphthol-4-sulfonic acid, and phenols such as P- Examples of the alkyl sulfuric acid include ethyl hydroxybenzoate, pentachlorophenol, etc., and alkali metal salt compounds such as sodium and potassium such as lauryl sulfate. Further, specific examples of the hydroxides or carbonates of these alkali metals include sodium hydroxide and potassium hydroxide as the former, and sodium carbonate and potassium carbonate as the latter.

現像液の現像性、安定性等からみて、最も好ま
しい現像液としては、P−クロル安息香酸ナトリ
ウム、サリチル酸ナトリウムの単独または混合物
と、水酸化ナトリウム、水酸化カリウムの単独ま
たは混合物との水溶液をあげることができる。現
像液の濃度としては通常4から40重量%の水溶液
として使用することができるが、現像性を改善す
る目的で、メチルアルコール、エチルアルコー
ル、イソプロピルアルコール、ベンジルアルコー
ル等の有機溶剤をこれら現像液に対し重量で1か
ら40%添加することもできる。
In view of the developability, stability, etc. of the developer, the most preferable developer is an aqueous solution of sodium P-chlorobenzoate, sodium salicylate, alone or in a mixture, and sodium hydroxide, potassium hydroxide, alone or in a mixture. be able to. The concentration of the developer can usually be used as an aqueous solution of 4 to 40% by weight, but for the purpose of improving developability, organic solvents such as methyl alcohol, ethyl alcohol, isopropyl alcohol, benzyl alcohol, etc. are added to these developers. It is also possible to add 1 to 40% by weight.

[実施例] 厚さ100μのポリエチレンテレフタレートフイ
ルム上に下記の組成の感光液を塗布乾燥し、3μ
の着色した感光層をもつ感光性フイルムを得た。
[Example] A photosensitive liquid with the following composition was applied onto a polyethylene terephthalate film with a thickness of 100μ and dried.
A photosensitive film having a colored photosensitive layer was obtained.

ポリビニルホルマール(チツソ(株)社製 商品名
ビニリツクF) 10重量部 2−ジアゾ−1−ナフトール−5(4′−メチル
フエニルスルホネート) 3重量部 青色有機染料 1重量部 1、2−ジクロルエタン 86重量部 この感光性フイルムをポジ原稿と密着させ、超
高圧水銀灯2kwで1mの距離より、60秒露光した
後、以下の現像液で処理することにより、明色の
鮮明なポジ画像を得た。
Polyvinyl formal (manufactured by Chitsuso Co., Ltd., trade name Vinyric F) 10 parts by weight 2-diazo-1-naphthol-5 (4'-methylphenylsulfonate) 3 parts by weight Blue organic dye 1 part by weight 1,2-dichloroethane 86 Weight: This photosensitive film was placed in close contact with a positive original, exposed for 60 seconds from a distance of 1 meter using a 2kw ultra-high pressure mercury lamp, and then treated with the following developer to obtain a clear, bright positive image.

現像液 P−クロル安息芳香酸ナトリウム 20重量部 水酸化ナトリウム 1重量部 水 79重量部 [発明の効果] 本発明の感光性組成物によれば、皮膜が強靭で
レリーフがシヤープな良好な画像が得られ、又有
機溶剤を使用しないので作業性も良い。
Developer solution P - Sodium chlorobenzoate 20 parts by weight Sodium hydroxide 1 part by weight Water 79 parts by weight [Effect of the invention] According to the photosensitive composition of the present invention, a good image with a strong film and sharp relief can be produced. Moreover, since no organic solvent is used, the workability is also good.

Claims (1)

【特許請求の範囲】[Claims] 1 高分子化合物とオルソキノンジアジドとを含
有する感光性組成物において、前記高分子化合物
としてポリビニールホルマールを主成分として用
いたことを特徴とする被膜形成性の感光性組成
物。
1. A film-forming photosensitive composition containing a polymer compound and orthoquinonediazide, characterized in that polyvinyl formal is used as the main component as the polymer compound.
JP14090783A 1983-08-01 1983-08-01 Photosensitive composition Granted JPS59187340A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP14090783A JPS59187340A (en) 1983-08-01 1983-08-01 Photosensitive composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP14090783A JPS59187340A (en) 1983-08-01 1983-08-01 Photosensitive composition

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
JP56156961A Division JPS5858546A (en) 1981-10-02 1981-10-02 Photosensitive mask material for photoengraving

Related Child Applications (1)

Application Number Title Priority Date Filing Date
JP1060496A Division JPH0680462B2 (en) 1989-03-13 1989-03-13 Photosensitive film and developing method thereof

Publications (2)

Publication Number Publication Date
JPS59187340A JPS59187340A (en) 1984-10-24
JPH0253778B2 true JPH0253778B2 (en) 1990-11-19

Family

ID=15279579

Family Applications (1)

Application Number Title Priority Date Filing Date
JP14090783A Granted JPS59187340A (en) 1983-08-01 1983-08-01 Photosensitive composition

Country Status (1)

Country Link
JP (1) JPS59187340A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2808457B2 (en) * 1989-06-17 1998-10-08 コニカ株式会社 A photosensitive lithographic printing plate that does not require dampening water
JP2849623B2 (en) * 1989-08-15 1999-01-20 コニカ株式会社 Image forming method
JP2849624B2 (en) * 1989-08-15 1999-01-20 コニカ株式会社 Image forming method

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5011022A (en) * 1973-05-29 1975-02-04
JPS5096304A (en) * 1973-12-27 1975-07-31
JPS5463818A (en) * 1977-09-22 1979-05-23 Hoechst Ag Photosensitive copying composition
JPS556397A (en) * 1978-06-26 1980-01-17 Hoechst Ag Photosensitive mixture
JPS55129341A (en) * 1979-03-29 1980-10-07 Daicel Chem Ind Ltd Photosensitive covering composition
JPS56126836A (en) * 1980-03-11 1981-10-05 Ricoh Co Ltd Photosensitive lithographic original plate
JPS5858546A (en) * 1981-10-02 1983-04-07 Kimoto & Co Ltd Photosensitive mask material for photoengraving

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5011022A (en) * 1973-05-29 1975-02-04
JPS5096304A (en) * 1973-12-27 1975-07-31
JPS5463818A (en) * 1977-09-22 1979-05-23 Hoechst Ag Photosensitive copying composition
JPS556397A (en) * 1978-06-26 1980-01-17 Hoechst Ag Photosensitive mixture
JPS55129341A (en) * 1979-03-29 1980-10-07 Daicel Chem Ind Ltd Photosensitive covering composition
JPS56126836A (en) * 1980-03-11 1981-10-05 Ricoh Co Ltd Photosensitive lithographic original plate
JPS5858546A (en) * 1981-10-02 1983-04-07 Kimoto & Co Ltd Photosensitive mask material for photoengraving

Also Published As

Publication number Publication date
JPS59187340A (en) 1984-10-24

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