JPH03200970A - Pattern working method for photosensitive polymide - Google Patents

Pattern working method for photosensitive polymide

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Publication number
JPH03200970A
JPH03200970A JP22626189A JP22626189A JPH03200970A JP H03200970 A JPH03200970 A JP H03200970A JP 22626189 A JP22626189 A JP 22626189A JP 22626189 A JP22626189 A JP 22626189A JP H03200970 A JPH03200970 A JP H03200970A
Authority
JP
Japan
Prior art keywords
photosensitive polyimide
film
polyimide film
photosensitive
development
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
JP22626189A
Other languages
Japanese (ja)
Inventor
Masao Tomikawa
真佐夫 富川
Masuichi Eguchi
益市 江口
Masaya Asano
浅野 昌也
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.)
Toray Industries Inc
Original Assignee
Toray Industries Inc
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 Toray Industries Inc filed Critical Toray Industries Inc
Priority to JP22626189A priority Critical patent/JPH03200970A/en
Publication of JPH03200970A publication Critical patent/JPH03200970A/en
Pending legal-status Critical Current

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  • Photosensitive Polymer And Photoresist Processing (AREA)

Abstract

PURPOSE:To contrive the improvement in developability, the stabilization of developing time, the prevention of cracking, the improvement in resolution, etc., by applying a photosensitive polyimide coating agent on a substrate, then prebaking the coating to form a photosensitive polyimide film, subjecting the film selectively to a 2nd baking treatment after exposing developing the film and then subjecting the film to heating and baking. CONSTITUTION:The photosensitive polyimide coating material is applied on the substrate and is then prebaked to form the photosensitive polyimide film. After the photosensitive polyimide film is subjected to the selective exposing, this photosensitive polyimide film is subjected to the 2nd baking treatment and thereafter, the photosensitive polyimide film is developed and is then heated and baked. The photosensitive polyimide after the exposing is subjected to the rebaking treatment before the development in such a manner. The developability is greatly improved in this way and the generation of the cracking is obviated; in addition, the resolution is simultaneously improved.

Description

【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、感光性ポリイミドのパターン加工方法に関す
るものである。
DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a method for patterning photosensitive polyimide.

[従来の技術] 従来、半導体素子等への感光性ポリイミド系樹脂膜の形
成は次の工程で行われていた。
[Prior Art] Conventionally, the formation of a photosensitive polyimide resin film on a semiconductor element or the like has been performed in the following steps.

(1)  シリコンやセラミック等の基板上に感光性ポ
リイミド樹脂の前駆体の溶液を塗布した後、プリベーク
して感光性ポリイミド皮膜を形成する、■ 次いでこれ
を選択的に露光、すなわち最終的に残すべきポリイミド
膜の部分に光が当るようなフォトマスクを使用し、紫外
線を照射する、(3)現像する、 (4)  加熱焼成する。
(1) After applying a solution of a photosensitive polyimide resin precursor onto a substrate such as silicon or ceramic, prebaking is performed to form a photosensitive polyimide film, ■ This is then selectively exposed to light, that is, it is left as the final layer. Using a photomask that allows light to hit the part of the polyimide film to be treated, irradiate with ultraviolet rays, (3) develop, and (4) heat and bake.

しかしながら、かかる従来技術の場合、プリベーク処理
した感光性ポリイミド皮膜を露光した後、長時間放置し
た場合、現像性が低下し現像に長時間を要するという問
題があるうえ、しばしば得られたポリイミド樹脂膜のパ
ターンにクラックが入るという欠点を有していた。
However, in the case of such conventional technology, if the prebaked photosensitive polyimide film is left to stand for a long time after being exposed, the developability deteriorates and development takes a long time. This had the disadvantage that cracks appeared in the pattern.

このため、従来、感光性ポリイミドをパターン加工する
に際しては、プリベーク、露光、現像を連続して行う必
要があるなど工程管理上の制約があるうえ、これらを連
続的に行えない場合には、−旦塗布した感光性ポリイミ
ド膜を剥離して、再度塗布からやり直す必要があるなど
の問題があった。
For this reason, conventionally, when patterning photosensitive polyimide, there are constraints on process control, such as the need to perform prebaking, exposure, and development in succession, and if these cannot be performed continuously, - There are problems such as the need to peel off the photosensitive polyimide film that has been applied and start over again.

[発明が解決しようとする課題] 本発明者らは、このような従来技術の欠点に鑑み、その
改善策について鋭意検討した結果、露光後の感光性ポリ
イミド皮膜を現像前に再ベーク処理した場合には、現像
性が著しく向上するとともにクラックの発生がな(、し
かも解像度を同時に向上できることを知見し、本発明に
到達したものである。
[Problems to be Solved by the Invention] In view of the shortcomings of the prior art, the present inventors have conducted extensive studies on ways to improve the problem, and as a result, the present inventors have found that when the photosensitive polyimide film after exposure is re-baked before development. The present invention was achieved based on the discovery that the developability was significantly improved and no cracking occurred (and the resolution could be improved at the same time).

したがって、本発明の目的は感光性ポリイミドの現像を
行う際の現像性の向上ないし現像時間の安定化、クラッ
クの防止および解像度の向上等を同時に達成できる感光
性ポリイミドのパターン加工方法を提供することにある
Therefore, an object of the present invention is to provide a pattern processing method for photosensitive polyimide that can simultaneously improve developability, stabilize development time, prevent cracks, and improve resolution when developing photosensitive polyimide. It is in.

[課題を解決するための手段] かかる本発明の目的は、次の構成により達成される。[Means to solve the problem] This object of the present invention is achieved by the following configuration.

(1)次の(A)〜(E)の工程を経て順次パターン加
工することを特徴とする感光性ポリイミドのパターン加
工方法。
(1) A method for patterning photosensitive polyimide, which is characterized by sequentially patterning through the following steps (A) to (E).

(A)基板上に感光性ポリイミドコーティング剤を塗布
後、プリベークを行い、感光性ポリイミド皮膜を形成す
る工程、 (B)該感光性ポリイミド皮膜を選択的に露光する工程
、 (C)該感光性ポリイミド皮膜に第2のベーク処理を行
う工程、 (D)該感光性ポリイミド皮膜を現像する工程、(E)
加熱焼成する工程。
(A) After applying a photosensitive polyimide coating agent on the substrate, prebaking is performed to form a photosensitive polyimide film. (B) A step of selectively exposing the photosensitive polyimide film. (C) The photosensitive polyimide film is selectively exposed to light. (D) performing a second baking treatment on the polyimide film; (D) developing the photosensitive polyimide film; (E)
The process of heating and firing.

本発明において用いられる感光性ポリイミドコーティン
グ剤とはポリイミドまたはポリイミド前駆体に感光基を
導入、あるいは感光性化合物を混合し、紫外線、遠紫外
線、可視光線などの光への感応性を付与したものをいい
、公知の各種の感光性ポリイミドコーティング剤が使用
しうる。ここでポリイミド前駆体とは加熱焼成処理によ
りポリイミドを与えるものである。
The photosensitive polyimide coating agent used in the present invention is one in which a photosensitive group is introduced into polyimide or a polyimide precursor, or a photosensitive compound is mixed therein to impart sensitivity to light such as ultraviolet rays, far ultraviolet rays, and visible light. Various known photosensitive polyimide coating agents can be used. Here, the polyimide precursor is one that provides polyimide through heating and baking treatment.

次に本発明における感光性ポリイミドのパターン加工方
法について具体的に説明する。
Next, the method of patterning photosensitive polyimide in the present invention will be specifically explained.

まず、シリコン基板やセラミック基板のような半導体素
子あるいは半導体装置を実装した基板の表面に感光性ポ
リイミドコーティング剤を塗布した後、プリベークして
感光性ポリイミド皮膜を形成する。プリベーク温度は感
光性ポリイミドの膜厚に応じて適宜選択するのが好まし
いが、通常オープンの場合、50℃〜100℃で15分
から8時間、ホットプレートの場合、80℃〜120℃
の範囲で1分から30分程度行うことができる。
First, a photosensitive polyimide coating agent is applied to the surface of a substrate mounted with a semiconductor element or a semiconductor device, such as a silicon substrate or a ceramic substrate, and then prebaked to form a photosensitive polyimide film. The prebaking temperature is preferably selected appropriately depending on the film thickness of the photosensitive polyimide, but in the case of an open oven, it is usually 50°C to 100°C for 15 minutes to 8 hours, and in the case of a hot plate, it is 80°C to 120°C.
This can be done for about 1 minute to 30 minutes.

このようにしてプリベーク処理された感光性ポリイミド
皮膜は次いで選択的に露光されて所定のパターンに形成
される。露光はコンタクトアライナ−のような密着露光
、あるいはミラープロジェクションアライナ−やステッ
パーのような投影露光など公知の方式で行うことができ
る。
The photosensitive polyimide film prebaked in this way is then selectively exposed to form a predetermined pattern. Exposure can be performed by a known method such as contact exposure using a contact aligner or projection exposure using a mirror projection aligner or a stepper.

次いで所定パターンの施された感光性ポリイミド皮膜に
は、現像前に、第2のベーク処理が施される。第2のベ
ーク処理条件としてはプリベーク条件と同じかあるいは
より弱い条件が好ましく採用される。ここでより弱い条
件とはより弱い熱履歴が感光性ポリイミド皮膜に与えら
れるような条件を意味する。
Next, the photosensitive polyimide film provided with the predetermined pattern is subjected to a second baking treatment before development. As the second baking conditions, conditions that are the same as or weaker than the pre-bake conditions are preferably employed. Here, weaker conditions mean conditions such that a weaker thermal history is imparted to the photosensitive polyimide film.

通常ホットプレートの場合は80℃〜110℃の範囲で
30秒から5分の範囲で選ばれ、オーブンの場合は50
℃〜100℃の範囲で10分から90分の範囲で選択す
るのがパターン加工性の点から好ましい。
Usually, in the case of a hot plate, the temperature is selected in the range of 80°C to 110°C for 30 seconds to 5 minutes, and in the case of an oven, the temperature is set at 50°C.
From the point of view of pattern processability, it is preferable to select the temperature in the range of 10 minutes to 90 minutes in the range of 100 degrees Celsius to 100 degrees Celsius.

本発明における露光後、現像前の第2のベーク処理は、
本発明の目的ないし効果を効果的に達成するためには、
現像前の少なくとも4時間前に行うのが好ましい。
The second bake treatment after exposure and before development in the present invention is as follows:
In order to effectively achieve the objects and effects of the present invention,
Preferably, this is done at least 4 hours before development.

第2のベーク処理の施された感光性ポリイミド皮膜はつ
いで公知の方法により現像される。
The photosensitive polyimide film subjected to the second baking treatment is then developed by a known method.

現像液としては、N−メチル−2−ピロリドンやN、N
−ジメチルアセトアミドのような極性溶媒にメタノール
やエチレングリコールのようなアルコール系の溶剤、ア
セトンやシクロヘキサノンのようなケトン系の溶剤、ベ
ンゼンやキシレンのような芳香族炭化水素系の溶剤を加
えたものが使用でき、現像方式としてははスプレ一方式
、浸漬方式、超音波を加えた現像方式など公知の方法を
使用できる。
As a developer, N-methyl-2-pyrrolidone, N,N
-A polar solvent such as dimethylacetamide with an alcoholic solvent such as methanol or ethylene glycol, a ketone solvent such as acetone or cyclohexanone, or an aromatic hydrocarbon solvent such as benzene or xylene. As a developing method, a known method such as a spray method, a dipping method, or a developing method using ultrasonic waves can be used.

本発明における、感光性ポリイミドのパターン加工方法
は、感光基をジエチルアミノエチルメタクリレートのよ
うな光反応性を有する2重結合をもった3級アミンのよ
うな化合物をポリイミド前駆体に混合することにより感
光性を導入した感光性ポリイミドの場合に特に効果的で
あるが、感光基をエステル結合のような化学結合により
導入した感光性ポリイミドの場合にも効果が期待できる
The method of patterning photosensitive polyimide in the present invention involves mixing a photosensitive group with a compound such as a tertiary amine having a photoreactive double bond such as diethylaminoethyl methacrylate into a polyimide precursor. This method is particularly effective in the case of photosensitive polyimide into which a photosensitive group has been introduced, but it can also be expected to be effective in the case of a photosensitive polyimide into which a photosensitive group has been introduced through a chemical bond such as an ester bond.

所定の現像が終了後、公知の方法、例えば感光性ポリイ
ミド皮膜を200〜400℃の範囲で、連続的または段
階的に昇温しで、加熱焼成することにより所定のパター
ンを有するポリイミド樹脂膜の加工が完了する。
After the predetermined development is completed, a polyimide resin film having a predetermined pattern is formed by heating and baking the photosensitive polyimide film using a known method, e.g., heating the photosensitive polyimide film in a range of 200 to 400°C continuously or stepwise. Processing is completed.

[発明の効果] 本発明の感光性ポリイミドパターンのパターン加工方法
は上述のごとく露光後現像前に第2のべ一り処理を施す
ようにしたので、現像性が著しく向上するとともにクラ
ックの発生がなく、しかも解像度を同時に向上できる利
点がある。
[Effects of the Invention] As described above, in the pattern processing method for photosensitive polyimide patterns of the present invention, the second flattening treatment is performed after exposure and before development, so that the developability is significantly improved and the occurrence of cracks is reduced. However, there is an advantage that the resolution can be improved at the same time.

[実施例] 以下本発明を実施例により具体的に説明する。[Example] The present invention will be specifically explained below using examples.

以下、実施例を挙げて本発明を具体的に説明するが、本
発明はこれらに限定されない。
EXAMPLES Hereinafter, the present invention will be specifically explained with reference to Examples, but the present invention is not limited thereto.

実施例1 ベンゾフェノンテトラカルボン酸310gと4゜4′−
ジアミノジフェニルエーテル200gを2040gのN
−メチルピロリドン中で40℃で反応させて、粘度が1
30ポイズのポリアミド酸のワニスを得た。
Example 1 310 g of benzophenone tetracarboxylic acid and 4°4'-
200g of diaminodiphenyl ether and 2040g of N
- reacted in methylpyrrolidone at 40°C until the viscosity was 1.
A 30 poise polyamic acid varnish was obtained.

このワニスにジメチルアミノエチルメタクリレヘト34
0gとN−メチルピロリドン300 g’iミヒラーケ
トン12gを混合して感光性ポリイミド前駆体のワニス
(A)を得た。
Add 34 dimethylaminoethyl methacrylate to this varnish.
0 g of N-methylpyrrolidone and 12 g of Michler's ketone were mixed to obtain a photosensitive polyimide precursor varnish (A).

このワニス(A)をシリコーンウェハー上にスピンナを
用いて塗布後、100℃のホットプレートで3分間プリ
ベークし、膜厚5μのフィルムを作製した。
This varnish (A) was applied onto a silicone wafer using a spinner, and then prebaked on a hot plate at 100° C. for 3 minutes to produce a film with a thickness of 5 μm.

このものに、キャノン製マスクアライナ−へPLA−5
01を用いて300mjのテストパターンでの露光を行
った。
To this, Canon's mask aligner PLA-5
Exposure was performed using a test pattern of 300 mj using 01.

露光終了後、直ちに、90℃のホットプレートで1分間
処理する第2のベーク処理を行い、次いでN−メチルピ
ロリドンとメタノールが体積比で1=1の現像液中で浸
漬現像を行ったところ、未露光部の溶解時間は1分であ
り、2分の現像後に膜厚が4μで、10μのライン・ア
ンド・スペースが解像されていた。
Immediately after the exposure, a second baking process was performed on a hot plate at 90°C for 1 minute, and then immersion development was performed in a developer containing N-methylpyrrolidone and methanol in a volume ratio of 1=1. The dissolution time of the unexposed area was 1 minute, and after 2 minutes of development, the film thickness was 4 μm, and lines and spaces of 10 μm were resolved.

続いて150℃で30分および300℃で30分順次加
熱焼成処理を行ない良好な所定のパターンを有するポリ
イミド樹脂膜を得た。
Subsequently, heating and baking treatments were performed at 150° C. for 30 minutes and at 300° C. for 30 minutes to obtain a polyimide resin film having a good predetermined pattern.

実施例2 露光後2日間23℃、50%RHの雰囲気下に放置した
後現像を行った以外は実施例1と同じ条件で感光性ポリ
イミドのパターン加工を行った。
Example 2 Pattern processing of photosensitive polyimide was carried out under the same conditions as in Example 1, except that development was performed after being left in an atmosphere of 23° C. and 50% RH for 2 days after exposure.

未露光部の溶解時間は1分で、2分の現像後に膜厚が4
μで、10μのライン・アンド・スペースが解像されて
いた。
The dissolution time of the unexposed area was 1 minute, and the film thickness was 4 minutes after 2 minutes of development.
10μ lines and spaces were resolved.

実施例3 露光後2日間23℃、8o%RHの雰囲気下に放置した
後現像を行った以外は実施例1と同じ条件で感光性ポリ
イミドのパターン加工を行った。
Example 3 Patterning of photosensitive polyimide was carried out under the same conditions as in Example 1, except that development was performed after being left in an atmosphere of 23° C. and 80% RH for 2 days after exposure.

未露光部の溶解時間は1分10秒で、2分の現像後に膜
厚が4μで、15μのライン・アンド・スペースが解像
されていた。
The dissolution time of the unexposed area was 1 minute and 10 seconds, and after 2 minutes of development, the film thickness was 4 μm, and lines and spaces of 15 μm were resolved.

参考例 プリベーク後、すぐに露光し、現像前のベーク処理を行
うことなくただちに現像を行った以外は実施例1と同じ
条件でパターン加工を行ったところ。未露光部の溶解時
間は1分5秒となり、2分の現像後、膜厚が3.5μで
、15〜20μのライン・アンド・スペースに残膜が残
っていた。
Reference Example Pattern processing was carried out under the same conditions as in Example 1, except that after pre-baking, exposure was carried out immediately and development was carried out immediately without baking before development. The dissolution time of the unexposed area was 1 minute and 5 seconds, and after 2 minutes of development, the film thickness was 3.5 μm, and residual film remained in lines and spaces of 15 to 20 μm.

比較例1 露光後6時間、23℃、5o%RHの雰囲気下に放置し
たものについて、現像前に再度プリベークを行なわなか
った以外は実施例1と同じ条件でパターン加工を行った
ところ、未露光部の−溶解時間は2分30秒となり、3
分30秒の現像後、膜厚が3.5μで、50μのライン
・アンド・スペースにも残膜が残っていた。
Comparative Example 1 Pattern processing was carried out under the same conditions as in Example 1, except that pre-baking was not performed again before development on a product that was left in an atmosphere of 23°C and 5o% RH for 6 hours after exposure. The -dissolution time of part is 2 minutes 30 seconds, and 3
After development for minutes and 30 seconds, the film thickness was 3.5 μm, and residual film remained even in the 50 μm line and space.

比較例2 露光後8時間、23℃、80%RHの雰囲気下に放置し
たものについて現像前に第2のベーク処理を行わなかっ
た以外は実施例1と同じ条件で感光性ポリイミドのパタ
ーン加工を行った。露光部の溶解時間は5分以上となり
、7分の現像後に膜厚が2.5μで、50μのライン・
アンド・スペースにも残膜が残っていた。またパターン
のコーナ一部にもクラックが生じていた。
Comparative Example 2 Patterning of photosensitive polyimide was carried out under the same conditions as in Example 1, except that the second bake treatment was not performed before development, after being left in an atmosphere of 23 ° C. and 80% RH for 8 hours after exposure. went. The dissolution time of the exposed area was more than 5 minutes, and after 7 minutes of development, the film thickness was 2.5μ, and a line of 50μ was formed.
There was some residual film left on And Space as well. Cracks also appeared at some corners of the pattern.

Claims (1)

【特許請求の範囲】[Claims] (1)次の(A)〜(E)の工程を経て順次パターン加
工することを特徴とする感光性ポリイミドのパターン加
工方法。 (A)基板上に感光性ポリイミドコーティング剤を塗布
後、プリベークを行い、感光性ポリイミド皮膜を形成す
る工程、 (B)該感光性ポリイミド皮膜を選択的に露光する工程
、 (C)該感光性ポリイミド皮膜に第2のベーク処理を行
う工程、 (D)該感光性ポリイミド皮膜を現像する工程、 (E)加熱焼成する工程。
(1) A method for patterning photosensitive polyimide, which is characterized by sequentially patterning through the following steps (A) to (E). (A) After applying a photosensitive polyimide coating agent on the substrate, prebaking is performed to form a photosensitive polyimide film. (B) A step of selectively exposing the photosensitive polyimide film. (C) The photosensitive polyimide film is selectively exposed to light. (D) A step of developing the photosensitive polyimide film; (E) A step of heating and baking the polyimide film.
JP22626189A 1989-08-30 1989-08-30 Pattern working method for photosensitive polymide Pending JPH03200970A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP22626189A JPH03200970A (en) 1989-08-30 1989-08-30 Pattern working method for photosensitive polymide

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP22626189A JPH03200970A (en) 1989-08-30 1989-08-30 Pattern working method for photosensitive polymide

Publications (1)

Publication Number Publication Date
JPH03200970A true JPH03200970A (en) 1991-09-02

Family

ID=16842431

Family Applications (1)

Application Number Title Priority Date Filing Date
JP22626189A Pending JPH03200970A (en) 1989-08-30 1989-08-30 Pattern working method for photosensitive polymide

Country Status (1)

Country Link
JP (1) JPH03200970A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018038002A1 (en) * 2016-08-25 2018-03-01 富士フイルム株式会社 Process for producing layered product and process for producing electronic device

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018038002A1 (en) * 2016-08-25 2018-03-01 富士フイルム株式会社 Process for producing layered product and process for producing electronic device
JPWO2018038002A1 (en) * 2016-08-25 2019-04-11 富士フイルム株式会社 LAMINATE MANUFACTURING METHOD AND ELECTRONIC DEVICE MANUFACTURING METHOD

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