JPH0568692B2 - - Google Patents
Info
- Publication number
- JPH0568692B2 JPH0568692B2 JP59182587A JP18258784A JPH0568692B2 JP H0568692 B2 JPH0568692 B2 JP H0568692B2 JP 59182587 A JP59182587 A JP 59182587A JP 18258784 A JP18258784 A JP 18258784A JP H0568692 B2 JPH0568692 B2 JP H0568692B2
- Authority
- JP
- Japan
- Prior art keywords
- resist
- pattern
- forming
- acid ester
- resist 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 229920003986 novolac Polymers 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- -1 aromatic sulfonic acid ester Chemical class 0.000 claims description 5
- 229920002120 photoresistant polymer Polymers 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 2
- 230000001678 irradiating effect Effects 0.000 claims 1
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 8
- 230000018109 developmental process Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 229940117955 isoamyl acetate Drugs 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000059 patterning Methods 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 150000003459 sulfonic acid esters Chemical class 0.000 description 2
- WODGMMJHSAKKNF-UHFFFAOYSA-N 2-methylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(C)=CC=C21 WODGMMJHSAKKNF-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 238000001312 dry etching Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000010897 surface acoustic wave method Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Description
【発明の詳細な説明】
（産業上の利用分野）
この発明は半導体装置等の製造に際してのレジ
ストパターンの形成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 forming a resist pattern during the manufacture of semiconductor devices and the like.
（従来の技術）
一般に半導体装置等の製造に際し、基板上に金
属層あるいは絶縁物層等の被着層のパターンを形
成する方法としては、エツチングによる方法及び
リフトオフを用いる方法がある。(Prior Art) In general, when manufacturing semiconductor devices, etc., methods of forming a pattern of an adhered layer such as a metal layer or an insulating layer on a substrate include a method using etching and a method using lift-off.
前記のリフトオフを用いる方法は、作業が簡便
であり、又エツチングの困難な金属でも容易に加
工でき、更に、特にドライエツチングに際して問
題になる基板へのダメージが発生しない優れた利
点がある。 The above-mentioned method using lift-off has the advantage that it is easy to work, can easily process metals that are difficult to etch, and does not cause damage to the substrate, which is a problem especially during dry etching.
しかしながらこのようなリフトオフに際してマ
スクとしてレジストを用いる場合には、該レジス
ト膜の断面形状、溶解性等に関し厳しい条件が要
求される。 However, when a resist is used as a mask during such lift-off, strict conditions are required regarding the cross-sectional shape, solubility, etc. of the resist film.
即ちリフトオフにより容易に被着層がパターニ
ングされ得るためには、該レジスト膜上に被着さ
れた被着層がレジストの溶解と共に容易に除去し
得ることが必要であること、及びこのためにはパ
ターン形成されたレジスト膜の断面形状が所謂オ
ーバーハング形状となつていることが強く要求さ
れる。 That is, in order for the deposited layer to be easily patterned by lift-off, it is necessary that the deposited layer deposited on the resist film can be easily removed as the resist is dissolved; It is strongly required that the cross-sectional shape of the patterned resist film has a so-called overhang shape.
かかるオーバーハング形状を得るために現在レ
ジストを多層化するか、又はポジ型フオトレジス
ト、例えばAZ−1350J（shipley社製フオトレジス
トの商品名）を用いクロロベンゼン処理を行うな
どの手段がとられている。 In order to obtain such an overhang shape, current methods include multilayering the resist, or using a positive photoresist such as AZ-1350J (trade name of a photoresist manufactured by Shipley) and performing chlorobenzene treatment. .
（発明が解決しようとする問題点）
しかし他方、これらの処理手段はその作業が煩
雑であり、又スループツト性に劣り、更にそのパ
ターン再現性が必ずしも良好とは云いがたい問題
があつた。そして今後、半導体デバイス等に対し
てはその集積度が益々高まり、したがつてサブミ
クロンのパターンが必要となるため該レジストに
対しては著しい高解像性が要求される機運にあ
る。(Problems to be Solved by the Invention) However, on the other hand, these processing means have problems in that their operations are complicated, their throughput is poor, and their pattern reproducibility is not necessarily good. In the future, the degree of integration of semiconductor devices and the like will continue to increase, and as a result, submicron patterns will become necessary, so there is an opportunity for resists to have extremely high resolution.
更に上記リフトオフプロセスの作業性を向上さ
せるためには、現像のみでレジスト膜断面にオー
バーハング形状を形成することが要求されるが、
かかる現像で用いる現像液はアルカリ水溶液に比
べて安定でかつ取扱いやすい有機溶剤を用いるこ
とが有利である。 Furthermore, in order to improve the workability of the lift-off process, it is required to form an overhang shape on the cross section of the resist film only by development.
As the developer used in such development, it is advantageous to use an organic solvent which is more stable and easier to handle than an alkaline aqueous solution.
結局高感度でありかつサブミクロンを解像でき
る高解像性を有し、上述の如き有機溶剤で現像が
行われしかも該現像後のレジスト断面がオーバー
ハング形状を有し、得られたレジストパターンが
他の有機溶剤で容易に除去し得る如きレジストパ
ターンの形成方法の開発が強く望まれているのが
実情である。 After all, it has high sensitivity and high resolution capable of resolving submicrons, and is developed with the above-mentioned organic solvent, and the cross section of the resist after said development has an overhang shape, resulting in a resist pattern. The reality is that there is a strong desire to develop a method for forming resist patterns that can be easily removed using other organic solvents.
（問題点を解決するための手段）
本発明は、基板上に、ノボラツク樹脂のベンゼ
ン、アルキルベンゼン、ナフタリン、アルキルナ
フタリンの群から選ばれたスルホン酸エステルの
皮膜を形成し、この皮膜に短波長の紫外線を選択
的に照射して露光し、有機溶剤を用いて現像する
ことを特徴とする高感度でかつサブミクロンの解
像力を有し、しかも現像のみでオーバーハングを
形成できるネガレジストのパターン形成方法であ
る。(Means for Solving the Problems) The present invention forms a film of a sulfonic acid ester selected from the group of novolac resins benzene, alkylbenzene, naphthalene, and alkylnaphthalene on a substrate, and this film is coated with a short wavelength light. A negative resist pattern forming method that has high sensitivity and submicron resolution, and is capable of forming overhangs only by development, which is characterized by selectively exposing to ultraviolet rays and developing using an organic solvent. It is.
（発明の作用）
この発明は特に後記実施例によつても明らかな
如く、上記のノボラツク樹脂のベンゼン又はナフ
タリン等のスルホン酸エステルをレジスト材料と
して用い遠紫外線により露光し、有機溶剤で現像
することによつて高感度でかつサブミクロンのレ
ジストパターンを形成し得るものであり、しかも
該レジストの断面は上記リフトオフに適したオー
バーハング形状を呈することになる。これに対し
比較例のノボラツク樹脂のみのレジストでは具体
的に50秒の露光を行つてもパターニングが得られ
ないのである。即ち上記ベンゼンスルホン酸エス
テル及びナフタリンスルホン酸エステル等のレジ
ストがエステル化されていることにより上記のネ
ガレジストパターンが形成できるのである。又、
本発明の上述のレジストは、現像時に酢酸イソア
ミル等の有機溶媒による露光部が膨潤しないた
め、レジストパターンの膨潤がほとんど起こらな
いこと等により、上記オーバーハング形状が良好
に保持されるのである。そして又波長200〜280n
ｍでのこれらの本発明のレジストは光吸収が大で
あり、該オーバーハングにより光が底部まで通過
せず本発明の作用を奏するものと考えられる。(Function of the Invention) As is particularly clear from the Examples described below, the present invention is based on the method of using a sulfonic acid ester such as benzene or naphthalene of the above-mentioned novolac resin as a resist material, exposing it to deep ultraviolet rays, and developing it with an organic solvent. By this method, it is possible to form a submicron resist pattern with high sensitivity, and the cross section of the resist exhibits an overhang shape suitable for the above-mentioned lift-off. On the other hand, with the resist made only of novolak resin in the comparative example, patterning could not be obtained even if exposure was carried out for 50 seconds. That is, the above-mentioned negative resist pattern can be formed by esterifying the resist such as the above-mentioned benzenesulfonic acid ester and naphthalene sulfonic acid ester. or,
In the above-mentioned resist of the present invention, the exposed area is not swollen by an organic solvent such as isoamyl acetate during development, so the resist pattern hardly swells, and the overhang shape is well maintained. And also wavelength 200~280n
It is thought that these resists of the present invention at m have a large light absorption, and the overhang prevents light from passing through to the bottom, thereby achieving the effect of the present invention.
（実施例） 以下実施例により本発明を具体的に説明する。(Example) The present invention will be specifically explained below using Examples.
実施例 １
レジスト材料としてノボラツク樹脂の１−ナフ
タリンスルホン酸エステル（NR−１）を用い
た。このNR−１をメチルセロソルブアセテート
に溶解した溶液をフイルターで濾過し、シリコン
基板上に0.5μｍの厚さで塗布レジスト膜を形成し
た。Example 1 A novolak resin 1-naphthalenesulfonic acid ester (NR-1) was used as a resist material. A solution of NR-1 dissolved in methyl cellosolve acetate was filtered to form a coated resist film with a thickness of 0.5 μm on a silicon substrate.
次にこの基板を80℃で30分間熱処理し、500W、
Xe−Hgランプによる主として200〜280nｍ（コ
ルドミラーにより280nｍより長波長光はカツト）
の遠紫外線でマスク密着介在下で20秒間露光を行
つた。そして酢酸イソアミル５対シクロヘキサン
２（体積比）溶液を用い、23℃の温度で15秒間現
像し、パターニングを行つたところ0.75μｍのラ
インアンドスペースのネガパターンが解像されて
いることが確認された。 Next, this board was heat treated at 80℃ for 30 minutes, and
Mainly 200-280nm by Xe-Hg lamp (longer wavelength light than 280nm is cut by cord mirror)
Exposure was performed for 20 seconds with deep ultraviolet rays under close contact with a mask. Then, when patterning was performed using a solution of 5 parts isoamyl acetate and 2 parts cyclohexane (volume ratio) at 23°C for 15 seconds, it was confirmed that a 0.75 μm line-and-space negative pattern had been resolved. .
更に得られたレジストパターンの断面形状を走
査型電子顕微鏡（以下SEMと略す）で観察した
ところ、明らかに基板上のレジスト層の断面がオ
ーバーハングとなつていることが認められた。 Furthermore, when the cross-sectional shape of the obtained resist pattern was observed using a scanning electron microscope (hereinafter abbreviated as SEM), it was clearly observed that the cross-section of the resist layer on the substrate had an overhang.
実施例 ２
実施例１で形成したレジストパターン上に常法
の真空蒸着法により0.5μｍ厚さのAlを蒸着した。
然る後アセトン溶液中に浸漬させたところ、リフ
トオフが完全に行なわれ0.75μｍのラインアンド
スペースのAlパターンが得られた。Example 2 Al was deposited to a thickness of 0.5 μm on the resist pattern formed in Example 1 by a conventional vacuum deposition method.
When it was then immersed in an acetone solution, lift-off was completed and a 0.75 μm line-and-space Al pattern was obtained.
実施例 ３
レジスト材料としてノボラツク樹脂のＰ−トル
エンスルホン酸エステル（NR−２）を用い、露
光後に100℃で３分ベークを行つた外は実施例１
と略同様に行つた。次いでｎ−プロピルアセテー
ト１対シクロヘキサン２（同）の溶液を用い23℃
で20秒現像しパターニングを行つたところ、
0.75μｍのラインアンドスペースのネガパターン
が解像されたことが確認された。同様にして
SEMにてレジストの断面形状を観察したところ
明らかなオーバーハング形状が認められた。Example 3 Example 1 except that P-toluenesulfonic acid ester (NR-2) of novolak resin was used as the resist material and baking was performed at 100°C for 3 minutes after exposure.
I went about the same way. Next, a solution of 1 part n-propyl acetate and 2 parts cyclohexane (same) was used at 23°C.
After developing for 20 seconds and patterning,
It was confirmed that a 0.75 μm line and space negative pattern was resolved. in the same way
When the cross-sectional shape of the resist was observed using SEM, a clear overhang shape was observed.
実施例 ４
レジスト材料としてノボラツク樹脂の２−メチ
ルナフタリン−１−スルホン酸エステル（NR−
３）を用いた外は実施例１と同様に行つた。露光
後、酢酸イソアミル５対シクロヘキサン２（同）
の混合溶液にて23℃で10秒間現像を行つたとこ
ろ、0.5μｍのラインアンドスペースのネガパター
ンが解像された。得られたレジストパターンを同
様にSEM観察したところその断面は良好なオー
バーハングとなつていることが認められた。Example 4 Novolac resin 2-methylnaphthalene-1-sulfonic acid ester (NR-
The same procedure as in Example 1 was carried out except that 3) was used. After exposure, 5 parts isoamyl acetate to 2 parts cyclohexane (same)
When development was carried out for 10 seconds at 23°C with a mixed solution of 0.5 μm line and space negative pattern was resolved. When the obtained resist pattern was similarly observed by SEM, it was found that the cross section had a good overhang.
比較例
ノボラツク樹脂のみをレジスト材料として用い
た他は実施例１と同様に行つた。然る後上記Xe
−Hgランプにて50秒間露光を行い、酢酸イソア
ミル１対シクロヘキサン２（同）の溶液にて23℃
で20秒間現像を行つたところレジストのパターン
は形成し得なかつた。Comparative Example The same procedure as in Example 1 was carried out except that only novolak resin was used as the resist material. After that, the above Xe
- Exposure for 50 seconds with a Hg lamp, and use a solution of 1 part isoamyl acetate and 2 parts cyclohexane (same) at 23°C.
When the resist was developed for 20 seconds, no resist pattern could be formed.
（発明の効果）
以上の説明から明らかなように、本発明によれ
ば、特に上述のリフトオフによるパターン形成が
高精度でかつ著しく容易に実施できるなどの効果
を示し、特に高集積化された半導体装置、表面弾
性波素子、磁気バブル素子及び光応用部品の製造
に利用して好適でありその工業的利用価値は極め
て高い。(Effects of the Invention) As is clear from the above description, according to the present invention, the above-mentioned lift-off pattern formation can be carried out with high precision and extremely easily, and particularly in highly integrated semiconductors. It is suitable for use in manufacturing devices, surface acoustic wave devices, magnetic bubble devices, and optical application parts, and its industrial utility value is extremely high.
Claims (1)
キルベンゼン、ナフタリン又はアルキルナフタリ
ンの群から選ばれた芳香族スルホン酸エステルか
らなるレジスト皮膜を形成する工程、及びこのレ
ジスト皮膜に遠紫外線を選択的に照射して露光
し、未露光部を有機溶剤にて溶出する工程を含む
ことを特徴とするネガ型レジストのパターン形成
方法。1. A step of forming a resist film on a substrate, consisting of an aromatic sulfonic acid ester selected from the group of novolak resin benzene, alkylbenzene, naphthalene, or alkylnaphthalene, and selectively irradiating this resist film with deep ultraviolet rays. A method for forming a negative resist pattern, comprising the steps of exposing to light and eluting unexposed areas with an organic solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59182587A JPS6161152A (en) | 1984-09-03 | 1984-09-03 | Formation of pattern of negative type resist |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59182587A JPS6161152A (en) | 1984-09-03 | 1984-09-03 | Formation of pattern of negative type resist |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6161152A JPS6161152A (en) | 1986-03-28 |
| JPH0568692B2 true JPH0568692B2 (en) | 1993-09-29 |
Family
ID=16120891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59182587A Granted JPS6161152A (en) | 1984-09-03 | 1984-09-03 | Formation of pattern of negative type resist |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6161152A (en) |
-
1984
- 1984-09-03 JP JP59182587A patent/JPS6161152A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6161152A (en) | 1986-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |