JPS6037547A - Rubber-base photoresist composition - Google Patents
Rubber-base photoresist compositionInfo
- Publication number
- JPS6037547A JPS6037547A JP14699983A JP14699983A JPS6037547A JP S6037547 A JPS6037547 A JP S6037547A JP 14699983 A JP14699983 A JP 14699983A JP 14699983 A JP14699983 A JP 14699983A JP S6037547 A JPS6037547 A JP S6037547A
- Authority
- JP
- Japan
- Prior art keywords
- rubber
- glycidyl ether
- composition
- photoresist composition
- film
- 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.)
- Granted
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
- G03F7/085—Photosensitive compositions characterised by adhesion-promoting non-macromolecular additives
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
Abstract
Description
【発明の詳細な説明】 〔発明の技術分野〕 本発明は、ゴム系フォトレジスト組成物に関する。[Detailed description of the invention] [Technical field of invention] The present invention relates to rubber-based photoresist compositions.
一般に、環化ｙＪＩｌｊイソグレンを主体としたゴム系
フォトレジスト組成物は、フェノールノボラック系のボ
ッ型フォトレジスト組成物に比較して１機械的強度が高
くこれを塗布する基板に対する接着性が良好であること
が知られている。In general, rubber-based photoresist compositions based on cyclized yJIlj isogrene have higher mechanical strength and better adhesion to the substrate to which they are applied, compared to phenol novolac-based bottom-type photoresist compositions. It is known.
しかしながら、ゴム系フォトレノスト組成物を塗布する
半導体基板や半導体基板上に形成された二酸化ケイ累膜
中に、燐や砒素等の高濃度不純物が含まれている場合に
は、ゴム系フォトレジスト組成物であっても接着力は不
十分である。However, if the semiconductor substrate to which the rubber-based photoresist composition is applied or the silicon dioxide film formed on the semiconductor substrate contains high concentration impurities such as phosphorus or arsenic, the rubber-based photoresist composition may However, the adhesive force is insufficient.
これは、現像時にレジスト組成物と半導体基板等の界面
への現像液の浸透によシレジスト組成物からなる薄膜（
以下レジスト膜と記す。）の膨潤が起シ易く１部分的に
レジストパメーンが剥離するためである。特に、ディッ
プ現像に比べてスプレー現像の場合には、高圧力で迅速
に現像を行うためにレジスト膜の剥れが顕著となシ、量
産ラインの自動化に適さない問題がある。This is a thin film (
Hereinafter, it will be referred to as a resist film. ) is likely to swell, resulting in partial peeling of the resist membrane. In particular, in the case of spray development compared to dip development, there is a problem in that the peeling of the resist film is noticeable due to rapid development under high pressure, making it unsuitable for automation in mass production lines.
このような問題を解消するために、レゾスト膜を形成す
る下地面を予めヘキサメチルジシラザンにて改質してお
く方法（米国特許
３５４９３６８）、写真蝕刻工程の直前に高温熱処理を
施す方法（応物第４３巻第４号。In order to solve these problems, there is a method in which the underlying surface on which the resist film is formed is modified in advance with hexamethyldisilazane (U.S. Pat. No. 3,549,368), a method in which high-temperature heat treatment is performed immediately before the photolithographic process (reactive material Volume 43, No. 4.
１９７４．３３０ｐ）、或は、ゴム系フォトレジストと
して天然ゴムを用いる方法等が採用されている。しかし
ながら、ヘキサメチルジシラザンにて表面改質を行うも
のでは、 １ｔａｖｔ度隣や砒素を含んだ基板の場合に
は１表面改質速度が遅く、依然量産に適さない。また、
写真蝕刻工程の直前に高温熱処理を旅すものでは、６０
０〜８００ ℃、の高温熱処理を必要とするため、処理
時間が長くなると共に、高温熱処理のために工程が複雑
になる。また、天然ゴムからなるゴム系フォトレジスト
を使用するものでは５天然ゴムのため解像度が低下する
と共に、レジストロット間での性状の安定性が悪い。1974.330p), or a method using natural rubber as a rubber-based photoresist. However, in the case of surface modification using hexamethyldisilazane, the surface modification rate is slow in the case of substrates with 1 tavt degree or arsenic, and is still unsuitable for mass production. Also,
For those that undergo high-temperature heat treatment just before the photo-etching process, 60
Since high-temperature heat treatment of 0 to 800° C. is required, the treatment time becomes long and the process becomes complicated due to the high-temperature heat treatment. Furthermore, in those using a rubber-based photoresist made of natural rubber, the resolution is lowered due to the presence of natural rubber, and the stability of properties between resist lots is poor.
本発明は、接着性の向上を図ったゴム系フォトレジスト
組成物を提供することをその目的とするものである。An object of the present invention is to provide a rubber-based photoresist composition with improved adhesive properties.
本発明は、ゴム系フォトレジスト中にグリシジルエーテ
ル系化合物を含有したことにより。The present invention is achieved by containing a glycidyl ether compound in a rubber photoresist.
接着性の向上を図ったゴム系フォトレジスト組成物であ
る。This is a rubber-based photoresist composition with improved adhesive properties.
ここで、グリシジルエーテル系化合物としては、アリル
グリシジルエーテル、グリシジルメチルエーテル、ロー
ブナルグリシツルエーテル。Here, the glycidyl ether compounds include allyl glycidyl ether, glycidyl methyl ether, and lobinal glycidyl ether.
グリシジルフェニルエーテル等を使用するのが望ましい
。グリシジルエーテル系化合物の添加量は、多いほど接
着性を同上できるが、ゴム系フォトレジスト中に環化ポ
リイソプレン等の円形体樹脂に対して３〜１０重量％の
範囲で設定するのが望ましい。また、接着性を向上させ
る上で、グリシジルエーテル系化合物としてアリルグリ
シジルエーテルを用いるのが特に好ましい。It is preferable to use glycidyl phenyl ether or the like. The greater the amount of the glycidyl ether compound added, the better the adhesion as described above, but it is preferably set in the range of 3 to 10% by weight based on the circular resin such as cyclized polyisoprene in the rubber photoresist. Further, in order to improve adhesiveness, it is particularly preferable to use allyl glycidyl ether as the glycidyl ether compound.
以下１本発明の実施例について説明する。 An embodiment of the present invention will be described below.
実施例１
市販のゴム系フォトレジスト市販品ＡＪＣ，環化ポリイ
ソゾレンに対して５重量％のアリルグリシツルエーテル
を添加し、よく混合してゴム系フォトレジスト組成物（
実施例１）を得る。Example 1 Commercially available rubber-based photoresist 5% by weight of allyl glycytyl ether was added to the commercially available product AJC, cyclized polyisozolene, and mixed well to form a rubber-based photoresist composition (
Example 1) is obtained.
このフォトレゾスト組成物を半導体基板上の高濃度の燐
を含んだ二酸化ケイ素膜上に厚さ１μｍ塗布し、８０℃
、で１０分間プリベークした後。This photoresist composition was applied to a thickness of 1 μm on a silicon dioxide film containing high concentration of phosphorus on a semiconductor substrate, and then heated at 80°C.
, after pre-baking for 10 minutes.
１０秒間露光処理を施した。次に、これにキシレンとｎ
−へブタンの混合液からなる現像液で２０秒間スプレー
現像を施し、酢酸ｎ−ブチルでリンスした。二酸化ケイ
素膜上には、膨潤。Exposure treatment was performed for 10 seconds. Next, add xylene and n
- Spray development was performed for 20 seconds with a developer consisting of a mixture of hebutane and rinsed with n-butyl acetate. The silicon dioxide film swells.
プリップ等の起きていない極めて良好なレジストパター
ンが形成されていることを確認した。It was confirmed that an extremely good resist pattern was formed without any occurrence of prep or the like.
また、高濃度の燐を不純物拡散した半導体基板に、写真
蝕刻工程の直前に硫酸／過酸化水素の混合液で表面の親
水性処理を施した後に、実施例１のゴム系フォトレジス
ト組成物を塗布してレジスト膜を形成し、剥れ発生数及
び剥れ発生率（へ）を調べたところ下記表に示す結果を
得た。Further, the rubber-based photoresist composition of Example 1 was applied to a semiconductor substrate on which a high concentration of phosphorus was diffused as an impurity, after the surface was subjected to hydrophilic treatment with a mixed solution of sulfuric acid/hydrogen peroxide immediately before the photolithography process. A resist film was formed by coating, and the number of occurrences of peeling and the rate of peeling (f) were examined, and the results shown in the table below were obtained.
また、コゝム系フォトレジスト組成物中のアリルグリシ
ジルエーテルの含有量を０〜１０重量％の範囲で変化さ
せ、その際のレジスト膜の剥れ発生率％を調べたところ
１図に示す結果を得た。In addition, the content of allyl glycidyl ether in the comb-based photoresist composition was varied in the range of 0 to 10% by weight, and the peeling rate of the resist film was investigated. The results are shown in Figure 1. I got it.
実施例２
実施例１のゴム系フォトレジスト組成物のアリルグリシ
ジルエーテルに代えてｎ−ブチルグリシジルエーテルを
用いたゴム系フォトレゾスト組成物（実施例２）を使用
して、実施例１と同様の条件で二酸化ケイ素股上にレジ
スト膜を形成した。このレノスト膜も実施例１と同様に
膨潤 ｆリップ等の発生がなく、また現像例れのない良
好なものであることを確認した。また。Example 2 The same conditions as in Example 1 were carried out using a rubber-based photoresist composition (Example 2) in which n-butyl glycidyl ether was used in place of allyl glycidyl ether in the rubber-based photoresist composition of Example 1. A resist film was formed on the silicon dioxide layer. Similar to Example 1, this Rennost film was also confirmed to be of good quality, with no swelling, f-rip, etc., and no development problems. Also.
実施例１と同様の剥れ試験を行ったところ、下記表に併
記した結果を得た。When the same peeling test as in Example 1 was conducted, the results are shown in the table below.
実施例３
実施例２と同様に実施例１のゴム系フォトレジスト組成
物のアリルグリシジルエーテルに代えてグリシジルフェ
ニルエーテルを用いたゴム系フォトレゾスト組成物を使
用して二酸化ケイ素膜上にレゾスト膜を形成した。この
レジスト膜も実施例１と同様に膨潤、グリップ等の発生
がなく、また、現像例れのない良好なものであることを
確認した。また、実施例１と同様の剥れ試験を行ったと
ころ、下記表に併記した結果を得た。Example 3 Similarly to Example 2, a rubber-based photoresist composition using glycidyl phenyl ether instead of allyl glycidyl ether in the rubber-based photoresist composition of Example 1 was used to form a resist film on a silicon dioxide film. did. Similar to Example 1, this resist film was also confirmed to be of good quality without swelling, grip, etc., and with no problems in development. Further, when a peeling test similar to that in Example 1 was conducted, the results are also shown in the table below.
実施例４
実施例２．３と同様にしてグリシゾルメチルエーテルを
アリルグリシジルエーテルの代シに使用シたゴム系フォ
トレゾスト″ａ成物で形成したレジスト膜について同様
に調べたところ、膨潤、グリップ等の発生がなく、また
現像料れのない良好なものであることが判った。更に、
実施例１と同様の剥れ試験を行ったところ、下記表に併
記した結果を得た。Example 4 Similarly to Example 2.3, a resist film formed from a rubber-based photoresist "a" composition in which glycisol methyl ether was used as a substitute for allyl glycidyl ether was examined in the same manner, and swelling, grip, etc. It was found that the product was good, with no occurrence of oxidation, and no developer loss.
When the same peeling test as in Example 1 was conducted, the results are shown in the table below.
実施例５
実ｍ例１のゴム系フォトレジスト組成物を構成する支販
品Ａに代えて支販品Ｂを使用し、他は実施例１と全く同
様にしてアリルグリシジルエーテルを添加してゴム系フ
ォトレジスト組成物’？ｍ、このゴム系フォトレジスト
組成物を用いて実施例１と同様の条件で二酸化ケイ素膜
上にレジスト膜を形成した。形成されたレジスト膜は、
膨潤、プリップ等の発生がなく、まだ現像料れのない良
好なものであることを確認した。Example 5 Example 1 The rubber-based photoresist composition of Example 1 was prepared using commercially available product B instead of commercially available product A, and in the same manner as in Example 1, allyl glycidyl ether was added to form a rubber. '?-based photoresist compositions'? m. Using this rubber-based photoresist composition, a resist film was formed on a silicon dioxide film under the same conditions as in Example 1. The formed resist film is
It was confirmed that the product was in good condition with no swelling, prep, etc., and no developer loss.
表から明らかな如く１本発明のゴム系フォトレジスト組
成物は、極めて優れた接右性を有していることが判る。As is clear from the table, the rubber-based photoresist composition of the present invention has extremely excellent dextral properties.
就中、添加剤としてアリルグリシツルエーテルを用いた
ゴム系フォトレジスト組成物の場合にこの効果が顕著に
現われていることが判る。In particular, it can be seen that this effect is remarkable in the case of rubber-based photoresist compositions using allyl glycytyl ether as an additive.
以上説明した如く１本発明に係るゴム系フォトレジスト
組成物によれば、極めて潰れた接着性を有するものであ
る。As explained above, the rubber-based photoresist composition according to the present invention has extremely poor adhesion.
図は、レジスト膜の剥れ発生率と添加剤含有量との関係
を示す特性図である。
出願人代理人 弁理士 鈴 江 武 彦５１０
ＡカＰ／含祷＃ （Ｗｔ ’／、）The figure is a characteristic diagram showing the relationship between the peeling rate of the resist film and the additive content. Applicant's agent Patent attorney Takehiko Suzue 510 AkaP/Intimation # (Wt'/,)
Claims (1)
を含有してなることを特徴とするゴム系フォトレジスト
組成物。A rubber-based photoresist composition comprising a glycysol ether compound in the rubber-based photoresist.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14699983A JPS6037547A (en) | 1983-08-11 | 1983-08-11 | Rubber-base photoresist composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14699983A JPS6037547A (en) | 1983-08-11 | 1983-08-11 | Rubber-base photoresist composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6037547A true JPS6037547A (en) | 1985-02-26 |
| JPH0434740B2 JPH0434740B2 (en) | 1992-06-08 |
Family
ID=15420294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14699983A Granted JPS6037547A (en) | 1983-08-11 | 1983-08-11 | Rubber-base photoresist composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6037547A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63236029A (en) * | 1987-03-25 | 1988-09-30 | Fuji Photo Film Co Ltd | Photosoluble composition |
| JPH01161001A (en) * | 1987-10-16 | 1989-06-23 | Hoechst Ag | Photopolymerizable mixture |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6788524B2 (en) * | 2017-02-28 | 2020-11-25 | ダイコク電機株式会社 | Game equipment and playground system |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4920292A (en) * | 1972-06-16 | 1974-02-22 | ||
| JPS54113867A (en) * | 1978-02-27 | 1979-09-05 | Hitachi Ltd | Method of producing resistanceeequipped printed circuit board |
| JPS5523155A (en) * | 1978-08-08 | 1980-02-19 | Mitsubishi Rayon Co Ltd | Rubber-reinforced resin composition |
-
1983
- 1983-08-11 JP JP14699983A patent/JPS6037547A/en active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4920292A (en) * | 1972-06-16 | 1974-02-22 | ||
| JPS54113867A (en) * | 1978-02-27 | 1979-09-05 | Hitachi Ltd | Method of producing resistanceeequipped printed circuit board |
| JPS5523155A (en) * | 1978-08-08 | 1980-02-19 | Mitsubishi Rayon Co Ltd | Rubber-reinforced resin composition |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63236029A (en) * | 1987-03-25 | 1988-09-30 | Fuji Photo Film Co Ltd | Photosoluble composition |
| JPH01161001A (en) * | 1987-10-16 | 1989-06-23 | Hoechst Ag | Photopolymerizable mixture |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0434740B2 (en) | 1992-06-08 |
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