JP2582578B2 - Photosensitive resin composition - Google Patents
Photosensitive resin compositionInfo
- Publication number
- JP2582578B2 JP2582578B2 JP62173945A JP17394587A JP2582578B2 JP 2582578 B2 JP2582578 B2 JP 2582578B2 JP 62173945 A JP62173945 A JP 62173945A JP 17394587 A JP17394587 A JP 17394587A JP 2582578 B2 JP2582578 B2 JP 2582578B2
- Authority
- JP
- Japan
- Prior art keywords
- resin composition
- solution
- photosensitive resin
- photosensitive
- positive
- 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
Links
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
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- 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 本発明は感光性樹脂組成物に関し、更に詳しくは、感
光性印刷版（以下PS版と称す）及び集積回路作製用のフ
ォトレジストとして用いることのできる新規なポジ型感
光性樹脂組成物に関する。Description: TECHNICAL FIELD The present invention relates to a photosensitive resin composition, and more particularly, it can be used as a photosensitive printing plate (hereinafter, referred to as a PS plate) and a photoresist for producing an integrated circuit. The present invention relates to a novel positive photosensitive resin composition.
従来の技術 現在、ポジ型PS版、及びポジ型フォトレジストに用い
られている感光性樹脂組成物はそのほとんどが、ｏ−キ
ノンジアジド系化合物と、ノボラック型フェノール樹脂
とを混合あるいは縮合させたものである。2. Description of the Related Art Currently, most of the photosensitive resin compositions used for positive PS plates and positive photoresists are obtained by mixing or condensing an o-quinonediazide compound with a novolak phenol resin. is there.
ｏ−キノンジアジド系化合物は、紫外線照射により分
解しN2ガスを放出しかつ遊離のカルボン酸を生成する。
この性質を利用して、感光性樹脂上にポジフェルムを密
着し、紫外光で露光後、弱アルカリ水溶液で現像する
と、露光部分が溶出して除去され、未露光部は除去され
ずに残り、ポジ画像を形成する。しかしながらｏ−キノ
ンジアジド系化合物は、露光前、ポジフィルムと感光層
との密着が完全であっても光照射時に発生する窒素ガス
の影響で、一時的に密着が不均一になりボケが発生す
る。このボケによる版の損失をなくすため、PS版の表面
を粗面化する方法が報告されている（特公昭57−6582
号）。o- quinonediazide compound decomposes upon UV irradiation to release N 2 gas and to produce a free carboxylic acid.
Utilizing this property, a positive ferm is adhered onto a photosensitive resin, exposed to ultraviolet light, and then developed with a weak alkaline aqueous solution. When exposed with a weakly alkaline aqueous solution, the exposed portion is eluted and removed, and the unexposed portion remains without being removed. Form an image. However, even if the adhesion between the positive film and the photosensitive layer is complete before exposure, the o-quinonediazide-based compound temporarily becomes non-uniform due to the influence of nitrogen gas generated during light irradiation, causing blurring. In order to eliminate the loss of the plate due to the blur, a method of roughening the surface of the PS plate has been reported (Japanese Patent Publication No. 57-6852
issue).
また、微細加工用フォトレジストとして用いる場合、
ステッパーによる露光では、ポジマスクと露光層は密着
していないにもかかわらず、高照度短時間露光を行うた
め一時的に窒素ガスが多く発生し、ピンホールを形成す
る場合があり、基板エッチングの際に問題となることが
ある。さらに露光前に基板との密着性向上のため、120
℃以上でプリベークする必要がある場合、ｏ−キノンジ
アジド系化合物は熱で容易に分解し、樹脂と橋かけ結合
を形成することがある。When used as a photoresist for fine processing,
In the exposure using a stepper, even though the positive mask and the exposure layer are not in close contact with each other, a large amount of nitrogen gas is temporarily generated due to high-illuminance short-time exposure, and pinholes may be formed. Can be a problem. In addition, before exposure, 120
When it is necessary to pre-bake at a temperature of not less than ° C., the o-quinonediazide compound may be easily decomposed by heat and form a crosslinking bond with the resin.
発明が解決しようとする問題点 熱的負荷に対して敏感でなく、N2ガス等の無用なガス
の発生を伴うことのないようなポジ型感光性樹脂組成物
が望まれている。Problems to be Solved by the Invention There is a demand for a positive photosensitive resin composition which is not sensitive to a thermal load and does not involve generation of useless gas such as N 2 gas.
問題点を解決するための手段 本発明者等は、前記したような問題点を解決べく鋭意
研究を重ねた結果本発明に至ったものである。すなわち
本発明は一般式（Ｉ）及び／又は（II） （式中式（Ｉ）及び（II）においてＲはアルキル基を表
す。） で示されるアントラセン化合物とアルカリ可溶性高分子
化合物とからなるポジ型感光性樹脂組成物を提供する。Means for Solving the Problems The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have arrived at the present invention. That is, the present invention relates to the compound represented by the general formula (I) and / or (II) (Wherein, in the formulas (I) and (II), R represents an alkyl group). A positive photosensitive resin composition comprising an anthracene compound represented by the formula: and an alkali-soluble polymer compound.
式（Ｉ）及び／又は（II）で示される化合物をアルカ
リ可溶性高分子化合物に混合させたものは露光前、弱ア
ルカリ現像液に対する溶解速度は著しく減少し、露光後
その速度は著しく増大する。さらに露光時にはガスの発
生もなく、ボケ、ピンホールのないすぐれたポジ型画像
を与える。When the compound represented by the formula (I) and / or (II) is mixed with an alkali-soluble polymer compound, the dissolution rate in a weak alkali developing solution is significantly reduced before exposure, and the rate is significantly increased after exposure. Furthermore, no gas is generated at the time of exposure, and an excellent positive image without blur and pinholes is provided.
本発明による樹脂組成物中の式（Ｉ）及び（II）の光
反応機構は不明であるが、500nm以下の波長の光照射に
より、ニトロベンジル基が活性化され、エステル結合が
切断し、遊離のスルホン酸を生成するのでポジ型感光性
樹脂の溶解性を高めるものと考えられる。The photoreaction mechanism of the formulas (I) and (II) in the resin composition according to the present invention is unknown, but irradiation with light having a wavelength of 500 nm or less activates the nitrobenzyl group, cuts the ester bond and releases the nitrobenzyl group. It is considered that the sulfonic acid of the formula (1) is generated to enhance the solubility of the positive photosensitive resin.
本発明に用いられる式（Ｉ）及び（II）の感光性有機
化合物は以下のようにして合成される。即ちまずアント
ラキノンスルホン酸化合物を、水酸化ナトリウムあるい
は水酸化カリウムなどのアルカリ水溶液中、亜鉛、ある
いはハイドロサルファイトなどの還元剤を用いて70〜85
℃の温度で１〜２時間反応させ還元しロイコ体としたの
ち、50〜70℃の温度でこの反応液にジメチル硫酸、ジエ
チル硫酸、ジイソプロピル硫酸などの低級ジアルキル硫
酸、あるいはメチルトシレート、エチルトシレート、プ
ロピルトシレートなどのアルキルベンゼンスルホネート
などのアルキル化剤を滴下し、9,10−位をアルコキシ化
する。次に9,10−ジアルコキシ−アントラセンスルホン
酸をベンゼン、トルエンキシレンなどの芳香族炭化水素
あるいは、クロロホルム、塩化メチレン、四塩化炭素な
どの塩素系溶媒、あるいはテトラヒドロフラン、ジオキ
サンなどのエーテル系溶媒に分散させ、五塩化りんある
いは塩化チオニルなどの塩素化剤で30〜60℃で塩素化
し、9,10−ジアルコキシアントラセンスルホニルクロラ
イドとする。次に9,10−ジアルコキシアントラセンスル
ホニルクロライドおよびニトロベンジルアルコールをア
セトン、メチルエチルケトンなどのケトン系溶媒、ベン
ゼン、トルエン、キシレンなどの芳香族系炭化水素、テ
トラヒドロフラン、ジオキサン、ジエチルエーテルなど
のエーテル系溶媒に溶解させ、０℃〜10℃の温度で、水
酸化ナトリウム、水酸化カリウムなどのアルカリ水溶
液、あるいはトリエチルアミン、ピリジンなどのアミン
類を触媒として１〜６時間両者を反応させることによっ
て9,10−ジアルコキシアントラセンスルホン酸ニトロベ
ンジルエステルを得ることができる。例えば9,10−ジメ
トキシアントラセン−２−スルホン酸ｐ−ニトロベンジ
ルは、次の合成工程で得られる。The photosensitive organic compounds of the formulas (I) and (II) used in the present invention are synthesized as follows. That is, first, an anthraquinone sulfonic acid compound, in an aqueous alkaline solution such as sodium hydroxide or potassium hydroxide, zinc, or 70 to 85 using a reducing agent such as hydrosulfite.
At a temperature of 50 ° C. for 1 to 2 hours to form a leuco body. At a temperature of 50 to 70 ° C., the reaction mixture is mixed with a lower dialkyl sulfate such as dimethyl sulfate, diethyl sulfate, diisopropyl sulfate, or methyl tosylate or ethyl tosylate. An alkylating agent such as an alkylbenzenesulfonate such as acrylate or propyl tosylate is added dropwise, and the 9,10-position is alkoxylated. Next, 9,10-dialkoxy-anthracenesulfonic acid is dispersed in an aromatic hydrocarbon such as benzene and toluene xylene, or a chlorinated solvent such as chloroform, methylene chloride and carbon tetrachloride, or an ether-based solvent such as tetrahydrofuran and dioxane. Then, it is chlorinated with a chlorinating agent such as phosphorus pentachloride or thionyl chloride at 30 to 60 ° C. to obtain 9,10-dialkoxyanthracene sulfonyl chloride. Next, 9,10-dialkoxyanthracene sulfonyl chloride and nitrobenzyl alcohol are added to ketone solvents such as acetone and methyl ethyl ketone, aromatic hydrocarbons such as benzene, toluene and xylene, and ether solvents such as tetrahydrofuran, dioxane and diethyl ether. The mixture is dissolved at a temperature of 0 ° C. to 10 ° C. for 1 to 6 hours by using an aqueous alkaline solution such as sodium hydroxide or potassium hydroxide or an amine such as triethylamine or pyridine as a catalyst to react the 9,10-diamine. Alkoxyanthracene sulfonic acid nitrobenzyl ester can be obtained. For example, p-nitrobenzyl 9,10-dimethoxyanthracene-2-sulfonate is obtained in the following synthesis step.
本発明においてポジ型感光性有機化合物として用いら
れる式（Ｉ）又は（II）で示される化合物の具体例とし
ては次のようなものが挙げられるが、本発明はこれらに
限定されるものではない。 Specific examples of the compound represented by the formula (I) or (II) used as the positive photosensitive organic compound in the present invention include the following, but the present invention is not limited thereto. .
本発明に用いられるアルカリ可溶性高分子化合物とし
ては、フェノールノボラック樹脂、クレゾールノボラッ
ク樹脂、ポリビニルフェノール、メタクリル酸メチル−
メタクリル酸共重合体、スチレン−アクリル酸共重合
体、ポリビニルパラヒドロキシベンザールなどがある
が、これら以外のアルカリ可溶性高分子化合物で、本発
明に用いられる感光性有機化合物と相溶性のあるものは
使用することができる。 As the alkali-soluble polymer compound used in the present invention, phenol novolak resin, cresol novolak resin, polyvinyl phenol, methyl methacrylate-
There are methacrylic acid copolymer, styrene-acrylic acid copolymer, polyvinyl parahydroxybenzal, and the like, but other alkali-soluble polymer compounds that are compatible with the photosensitive organic compound used in the present invention. Can be used.
本発明の感光性樹脂組成物において、一般式（Ｉ）及
び／又は（II）の感光性有機化合物は、アルカリ可溶性
高分子に対して５重量パーセント〜50重量パーセント、
より好ましくは10重量パーセント〜30重量パーセント添
加される。又必要であれば少量のｏ−キノンジアジド系
化合物を混合しても良い。In the photosensitive resin composition of the present invention, the photosensitive organic compound represented by the general formula (I) and / or (II) is used in an amount of 5% by weight to 50% by weight based on the alkali-soluble polymer;
More preferably, 10 to 30 weight percent is added. If necessary, a small amount of an o-quinonediazide compound may be mixed.
本発明の感光性樹脂組成物は、通常適当な有機溶媒に
溶かして使用される。この有機溶媒としては、アセト
ン、メチルエチルケトン、シクロヘキサノンなどのケト
ン類、メチルセロソロブ、エチルセロソロブ、エチルセ
ロソロブアセテートなどのセロソロブ類、クロロホル
ム、四塩化炭素などの塩素化溶剤、酢酸エチル、酢酸ブ
チルなどのエステル系溶媒、ジメチルホルムアミドなど
のアミン類及びこれらの混合溶媒が用いられる。The photosensitive resin composition of the present invention is usually used by dissolving it in a suitable organic solvent. Examples of the organic solvent include ketones such as acetone, methyl ethyl ketone and cyclohexanone, cellosolobs such as methyl cellosolob, ethyl cellosolob, ethyl cellosolob acetate, chlorinated solvents such as chloroform and carbon tetrachloride, and esters such as ethyl acetate and butyl acetate. Solvents, amines such as dimethylformamide, and mixed solvents thereof are used.
本発明の感光性樹脂組成物は、さらに用途に応じて、
可塑剤、光変色剤、染料及び塗布性を良くするための添
加剤などが配合されて、通常前記したような溶媒に溶解
した上で印刷用アルミ板、プリント配線用銅板、フォト
エッチング用各種金属板及びシリコンウエハーなどの半
導体材料、あるいはフォトイメージング用のガラスフィ
ルム及びガラス板などに塗布される。The photosensitive resin composition of the present invention further depends on the application,
Plasticizers, photochromic agents, dyes, additives for improving coating properties, etc. are blended, and usually dissolved in the above-mentioned solvent, and then printed on aluminum plates, printed wiring copper plates, and various metals for photoetching. It is applied to a semiconductor material such as a plate and a silicon wafer, or a glass film and a glass plate for photo imaging.
本発明の感光性組成物の現像液としては、メタケイ酸
ナトリウム、りん酸ナトリウム、水酸化ナトリウム、水
酸化カリウム、炭酸ナトリウムなどの無機アルカリ水溶
液、あるいはテトラメチルアンモニウムハイドロキサイ
ド、トリエチルアミンなどの有機アミン水溶液が用いら
れる。As the developer of the photosensitive composition of the present invention, sodium metasilicate, sodium phosphate, sodium hydroxide, potassium hydroxide, an aqueous solution of an inorganic alkali such as sodium carbonate, or an organic amine such as tetramethylammonium hydroxide or triethylamine An aqueous solution is used.
実施例 実施例によって本発明を更に具体的に説明するが本発
明は以下の実施例に限定されるものではない。Examples The present invention will be described more specifically by way of examples, but the present invention is not limited to the following examples.
参考例（合成例） 500mlの４つ口フラスコにアントラキノン−２−スル
ホン酸ナトリウム15.51gと亜鉛末5g及びエタノール20ml
を加え撹拌し分散させた。この液に20％水酸化ナトリウ
ム水溶液を100g添加したあと、温度をあげ、１時間還流
させた。反応液は暗赤色に溶解した。次にこの反応液に
ジメチル硫酸を徐々に60ml滴下した。冷却後、析出物を
取し、ハイドロサルファイト水溶液で洗浄し未反応の
アントラキノン−２−スルホン酸ナトリウムを除いた。
次に生成物を大量の熱水に溶解し、過して亜鉛を取り
除いたあと、水を留去し10gの9,10−ジメトキシアント
ラセン−２−スルホン酸ナトリウムを得た。Reference Example (Synthesis Example) In a 500 ml four-necked flask, 15.51 g of sodium anthraquinone-2-sulfonate, 5 g of zinc powder and 20 ml of ethanol
Was added and stirred and dispersed. After 100 g of a 20% aqueous sodium hydroxide solution was added to this solution, the temperature was raised and the mixture was refluxed for 1 hour. The reaction was dissolved in dark red. Next, 60 ml of dimethyl sulfate was gradually added dropwise to the reaction solution. After cooling, the precipitate was collected and washed with an aqueous hydrosulfite solution to remove unreacted sodium anthraquinone-2-sulfonate.
Next, the product was dissolved in a large amount of hot water, and zinc was removed by passing the solution. The water was distilled off to obtain 10 g of sodium 9,10-dimethoxyanthracene-2-sulfonate.
9,10−ジメトキシアントラセン−２−スルホン酸ナト
リウム10gをベンゼン40mlに分散させ、徐々に５塩化り
ん12gを加えた。30分室温で撹拌したあと、過を行い
液を冷水で洗浄し、ベンゼン溶液を分離、塩化カルシ
ウムで乾燥させた。過後ベンゼンを留去することによ
り9gの9,10−ジメトキシアントラセン−２−スルホニル
クロライドを得た。10 g of sodium 9,10-dimethoxyanthracene-2-sulfonate was dispersed in 40 ml of benzene, and 12 g of phosphorus pentachloride was gradually added. After stirring at room temperature for 30 minutes, the mixture was filtered and the solution was washed with cold water, and the benzene solution was separated and dried with calcium chloride. After that, benzene was distilled off to obtain 9 g of 9,10-dimethoxyanthracene-2-sulfonyl chloride.
200mgの４つ口フラスコに13.5gの9,10−ジメトキシア
ントラセン−２−スルホニルクロライド、6.14gのｐ−
ニトロベンジルアルコール及びテトラヒドロフラン40ml
を加え、５℃以下で30％水酸化ナトリウム水溶液を6g徐
々に滴下した。10℃以下で３時間撹拌後、水100mlを加
え、25〜30℃で30分撹拌後、析出物を取、水、メタノ
ールの順に洗浄し、15gの9,10−ジメトキシアントラセ
ン−２−スルホン酸ｐ−ニトロベンジルエステルを得
た。In a 200 mg four-necked flask, 13.5 g of 9,10-dimethoxyanthracene-2-sulfonyl chloride, 6.14 g of p-
Nitrobenzyl alcohol and tetrahydrofuran 40 ml
And 6 g of a 30% aqueous sodium hydroxide solution was gradually added dropwise at 5 ° C. or lower. After stirring at 10 ° C or less for 3 hours, 100 ml of water was added, and the mixture was stirred at 25 to 30 ° C for 30 minutes. The precipitate was washed with water and methanol in that order, and 15 g of 9,10-dimethoxyanthracene-2-sulfonic acid was added. The p-nitrobenzyl ester was obtained.
（クロロホルム中でのλmax400nm） 実施例１ クロロホルム200gにクレゾールノボラック樹脂40gと
前記合成例でえた9,10−ジメトキシアントラセン−２−
スルホン酸ｐ−ニトロベンジル12g、オイルブルー＃603
（検版用色素）0.02gとからなる樹脂組成物を溶かして
過し感光液とした。これを砂目立てした平版用アルミ
板に膜厚2.0μｍになるように塗布、乾燥してPS版を作
成した。このPS版にポジフィルムを密着して、450W超高
圧水銀灯を用いて距離60cmより30秒露光し、次に４％メ
タケイ酸ナトリウム水溶液で現像、水洗しインキングし
たところ非画線部に汚れのない強固なポジ画像が得られ
た。露光時にはガスの発生もなくボケのない良好なPS版
を得ることができた。(Λmax 400 nm in chloroform) Example 1 40 g of cresol novolak resin in 200 g of chloroform and 9,10-dimethoxyanthracene-2- obtained in the above synthesis example.
12 g of p-nitrobenzyl sulfonate, oil blue # 603
(Dye for plate inspection) A resin composition comprising 0.02 g was dissolved and passed to obtain a photosensitive solution. This was applied to a grained lithographic aluminum plate so as to have a thickness of 2.0 μm and dried to prepare a PS plate. A positive film was adhered to this PS plate, exposed to light from a distance of 60 cm for 30 seconds using a 450 W ultra-high pressure mercury lamp, and then developed with a 4% aqueous solution of sodium metasilicate, washed with water and inked. No strong positive image was obtained. At the time of exposure, a good PS plate without gas generation was obtained without blur.
実施例２ シクロヘキサノン500gにフェノールノボラック樹脂15
0gと9,10−ジエトキシアントラセン−２−スルホン酸ｐ
−ニトロベンジル15gとからなる樹脂組成物を溶かし
過して感光液とした。この感光液をシリコンウエハー上
に回転塗布した。このウエハーを100℃の熱風乾燥機で2
0分間ベークし1.0μｍの膜厚を得た。ポジマスクを通し
て高圧水銀灯で15秒露光し、2.4％テトラメチルアンモ
ニウムハイドロキサイド水溶液で現像後、水洗し、120
℃で10分間ポストベークを行ったところ、サイドエッチ
のない解像度のすぐれたポジ型レジスト膜がえられた。Example 2 Phenol novolak resin 15 in 500 g of cyclohexanone
0 g and 9,10-diethoxyanthracene-2-sulfonic acid p
A resin composition comprising 15 g of nitrobenzyl was dissolved and passed to obtain a photosensitive solution. This photosensitive solution was spin-coated on a silicon wafer. This wafer is dried in a hot air dryer at 100 ° C for 2 hours.
Baking was performed for 0 minutes to obtain a film thickness of 1.0 μm. Exposure with a high pressure mercury lamp for 15 seconds through a positive mask, development with a 2.4% aqueous solution of tetramethylammonium hydroxide, washing with water,
After post-baking at 10 ° C for 10 minutes, a positive resist film having excellent resolution without side etching was obtained.
実施例３ エチルセロソロブアセテート200gにポリビニルフェノ
ール40gと9,10−ジエトキシアントラセン−２−スルホ
ン酸ｏ−ニトロベンジル5gとからなる樹脂組成物を溶か
し、過して感光液とした。この感光液を真空蒸着した
アルミニウム基板上に回転塗布し、80℃の熱風乾燥機で
20分間乾燥した。ポジマスクを通して超高圧水銀灯で60
秒露光し、0.1mol/の水酸化ナトリウム水溶液で現像
し、水洗した。次にポストベークなしにリン酸−硝酸の
混合エッチング液で腐食したところアルミニウム基板
は、サイドエッチのない、しかもレジスト膜は全くおか
されないすぐれたポジ画像が得られた。Example 3 A resin composition composed of 40 g of polyvinylphenol and 5 g of o-nitrobenzyl 9,10-diethoxyanthracene-2-sulfonate was dissolved in 200 g of ethyl cellosolov acetate, and the mixture was passed to obtain a photosensitive solution. This photosensitive liquid is spin-coated on a vacuum-deposited aluminum substrate, and dried with a hot air dryer at 80 ° C.
Dry for 20 minutes. 60 with a high pressure mercury lamp through a positive mask
Exposure for 2 seconds, development with a 0.1 mol / sodium hydroxide aqueous solution, and washing with water. Next, when the aluminum substrate was corroded with a mixed etching solution of phosphoric acid and nitric acid without post-baking, an excellent positive image was obtained on the aluminum substrate without side etching and without damaging the resist film at all.
実施例４ クロロホルム200gにクレゾールノボラック樹脂40gと
9,10−ジエトキシアントラセン−2,6−ジスルホン酸ビ
ス（６−ニトロベンジル）5gとからなる樹脂組成物を溶
かし過して感光液とした。この感光液をガラス板に膜
厚0.8μｍとなるように回転塗布した。これをポジマス
クを通して超高圧水銀灯で露光し、2.5％炭酸ナトリウ
ム水溶液でスプレー現像後、水洗したところ、きれの良
いポジ型のレジスト像が得られた。Example 4 200 g of chloroform and 40 g of cresol novolak resin
A resin composition comprising 5 g of bis (6-nitrobenzyl) 9,10-diethoxyanthracene-2,6-disulfonic acid was dissolved and filtered to obtain a photosensitive solution. This photosensitive solution was spin-coated on a glass plate to a thickness of 0.8 μm. This was exposed to an ultra-high pressure mercury lamp through a positive mask, spray-developed with a 2.5% aqueous solution of sodium carbonate, and washed with water. As a result, a clear positive resist image was obtained.
発明の効果 熱に対する安定性にすぐれ、光照射によるガス発生が
なく、エッチング液に対する耐性にすぐれたアルカリ現
像可能なポジ型感光性樹脂組成物が得られた。Effect of the Invention A positive photosensitive resin composition which is excellent in heat stability, has no gas generation due to light irradiation, and has excellent resistance to an etching solution, and which can be alkali-developed is obtained.
Claims (1)
で示されるアントラセン化合物とアルカリ可溶性高分子
化合物とからなるポジ型感光性樹脂組成物(1) The following formula (I) and / or (II) (In the formulas (I) and (II), R represents an alkyl group)
Positive photosensitive resin composition comprising an anthracene compound represented by formula (I) and an alkali-soluble polymer compound
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62173945A JP2582578B2 (en) | 1987-07-14 | 1987-07-14 | Photosensitive resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62173945A JP2582578B2 (en) | 1987-07-14 | 1987-07-14 | Photosensitive resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6418143A JPS6418143A (en) | 1989-01-20 |
| JP2582578B2 true JP2582578B2 (en) | 1997-02-19 |
Family
ID=15969978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62173945A Expired - Lifetime JP2582578B2 (en) | 1987-07-14 | 1987-07-14 | Photosensitive resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2582578B2 (en) |
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Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS613141A (en) * | 1984-06-15 | 1986-01-09 | Toshiba Corp | Photosensitive composition |
-
1987
- 1987-07-14 JP JP62173945A patent/JP2582578B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6418143A (en) | 1989-01-20 |
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