JPH01133045A - Resist pattern forming method - Google Patents
Resist pattern forming methodInfo
- Publication number
- JPH01133045A JPH01133045A JP62291350A JP29135087A JPH01133045A JP H01133045 A JPH01133045 A JP H01133045A JP 62291350 A JP62291350 A JP 62291350A JP 29135087 A JP29135087 A JP 29135087A JP H01133045 A JPH01133045 A JP H01133045A
- Authority
- JP
- Japan
- Prior art keywords
- resist
- resist pattern
- resin
- cresol
- exposed
- 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
Links
- 238000000034 method Methods 0.000 title claims description 10
- 239000000463 material Substances 0.000 claims abstract description 8
- 238000007348 radical reaction Methods 0.000 claims abstract description 7
- 239000002683 reaction inhibitor Substances 0.000 claims abstract description 6
- 239000000758 substrate Substances 0.000 claims description 5
- 230000007261 regionalization Effects 0.000 claims 1
- 229920005989 resin Polymers 0.000 abstract description 13
- 239000011347 resin Substances 0.000 abstract description 13
- 229920002120 photoresistant polymer Polymers 0.000 abstract description 7
- 239000003795 chemical substances by application Substances 0.000 abstract description 6
- 238000004132 cross linking Methods 0.000 abstract description 6
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 abstract description 6
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 abstract description 6
- -1 Naphthoquinone diazide sulfate Chemical class 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 229920003986 novolac Polymers 0.000 abstract description 4
- HTQNYBBTZSBWKL-UHFFFAOYSA-N 2,3,4-trihydroxbenzophenone Chemical compound OC1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 HTQNYBBTZSBWKL-UHFFFAOYSA-N 0.000 abstract description 3
- 230000001235 sensitizing effect Effects 0.000 abstract 3
- 229930192627 Naphthoquinone Natural products 0.000 abstract 1
- 230000001939 inductive effect Effects 0.000 abstract 1
- 238000004090 dissolution Methods 0.000 description 7
- 239000003504 photosensitizing agent Substances 0.000 description 6
- 238000007086 side reaction Methods 0.000 description 4
- BKZXZGWHTRCFPX-UHFFFAOYSA-N 2-tert-butyl-6-methylphenol Chemical compound CC1=CC=CC(C(C)(C)C)=C1O BKZXZGWHTRCFPX-UHFFFAOYSA-N 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- QVEIBLDXZNGPHR-UHFFFAOYSA-N naphthalene-1,4-dione;diazide Chemical compound [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1=CC=C2C(=O)C=CC(=O)C2=C1 QVEIBLDXZNGPHR-UHFFFAOYSA-N 0.000 description 2
- KGWYICAEPBCRBL-UHFFFAOYSA-N 1h-indene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)C=CC2=C1 KGWYICAEPBCRBL-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical compound [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000003381 stabilizer Substances 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
- G03F7/022—Quinonediazides
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
この発明は、基板上にポジ型レジスト材料を塗布し、マ
スクを介して露光後、現像によって所定のレジストパタ
ーンを得るレジストパターン形成方法に関するものであ
り、特に、高精度なレジストパターンを得ることのでき
る、レジストパターン形成方法に関するものである。[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a resist pattern forming method in which a positive resist material is applied onto a substrate, exposed through a mask, and then developed to obtain a predetermined resist pattern. In particular, the present invention relates to a resist pattern forming method capable of obtaining a highly accurate resist pattern.
［従来の技術］
従来、半導体デバイス等の製造工程では、基板上にフォ
トレジストを塗布した後、適当な露光用光源を用いて所
定のパターンを転写する。その後、現像により所定のレ
ジストパターンを得る。そして、このレジストパターン
をマスクとして、基板のエツチングが行なわれる。とこ
ろで、通常ポジ型フォトレジストとしては、ナフトキノ
ンジアジドを感光基として有するものが広く使われてい
る。[Prior Art] Conventionally, in the manufacturing process of semiconductor devices, etc., a photoresist is applied onto a substrate, and then a predetermined pattern is transferred onto the photoresist using an appropriate exposure light source. Thereafter, a predetermined resist pattern is obtained by development. Then, the substrate is etched using this resist pattern as a mask. Incidentally, as positive type photoresists, those having naphthoquinone diazide as a photosensitive group are commonly used.
たとえば、感光剤として２，３．４トリヒドロキシベン
ゾフエノンの１．２−ナフトキノンジアジドスルフォン
酸エステルをクレゾールノボラックレジンに添加したフ
ォトレジストでは、露光により、ナフトキノンジアジド
が光反応により、インデンカルボン酸に変化する。そし
−で、露光部分がアルカリ現像液に可溶となる。これに
より、現像時に選択的に露光部を除去し、所定のパター
ンを得ることができる。For example, in a photoresist in which 1,2-naphthoquinone diazide sulfonic acid ester of 2,3.4 trihydroxybenzophenone is added as a photosensitizer to cresol novolac resin, upon exposure, the naphthoquinone diazide undergoes a photoreaction and converts into indene carboxylic acid. Change. The exposed area then becomes soluble in the alkaline developer. Thereby, the exposed portion can be selectively removed during development to obtain a predetermined pattern.
［発明が解決しようとする問題点］
しかしながら、従来のポジ型フォトレジストでは、短波
長紫外線や、Ｘ線、電子ビーム等の露光では、レジスト
中の樹脂や感光剤が副反応を起こし、架橋を起こす。[Problems to be Solved by the Invention] However, in conventional positive photoresists, when exposed to short-wavelength ultraviolet rays, X-rays, electron beams, etc., the resin and photosensitizer in the resist undergo side reactions, resulting in crosslinking. wake up
第２図は、従来法により２５Ｏｎｍ付近の紫外光で露光
されたレジストの、現像液に対する溶解速度を露光エネ
ルギに対してプロットしたものである。図から明らかな
ように、露光量が成る値に達するまでは、溶解速度は増
加するが、露光量がそれ以上になると逆に溶解速度は減
少する。上述のとおり、レジスト中の樹脂や感光剤が副
反応を起こし、架橋を起こすからである。このため、現
像時に露光部のレジストが溶けきれず、残渣として残る
という問題点があった。露光部のレジストが残渣として
残ると、高精度なレジストパターンを得ることができな
い。FIG. 2 is a plot of the dissolution rate in a developer of a resist exposed to ultraviolet light of around 25 Onm by a conventional method versus exposure energy. As is clear from the figure, the dissolution rate increases until the exposure dose reaches a certain value, but when the exposure dose exceeds this value, the dissolution rate decreases. This is because, as described above, the resin and photosensitizer in the resist cause side reactions and crosslinking. For this reason, there was a problem in that the resist in the exposed area was not completely dissolved during development and remained as a residue. If the resist in the exposed area remains as a residue, a highly accurate resist pattern cannot be obtained.
この発明は、上記のような問題点を解決するためになさ
れたもので、露光部のレジストを完全に溶解し、残渣と
して残さないで、高精度なレジストパターンを得ること
のできるレジストパターン形成方法を提供することを目
的とする。This invention was made to solve the above-mentioned problems, and provides a resist pattern forming method that completely dissolves the resist in the exposed area and leaves no residue, thereby obtaining a highly accurate resist pattern. The purpose is to provide
［問題点を解決するための手段］
この発明は、基板上にポジ型レジスト材料を塗布し、マ
スクを介して露光後、現像によって所定のレジストパタ
ーンを得るレジストパターン形成方法に係るものである
。そして、前記問題点を解決するために、上記ポジ型レ
ジスト材料に、ラジカル反応禁止剤を添加して行なうこ
とを特徴とする。[Means for Solving the Problems] The present invention relates to a resist pattern forming method in which a positive resist material is applied onto a substrate, exposed through a mask, and then developed to obtain a predetermined resist pattern. In order to solve the above-mentioned problems, a radical reaction inhibitor is added to the above-mentioned positive resist material.
〔作用コ
この発明によるレジストパターン形成方法では、ラジカ
ル反応禁止剤を含宵したレジスト材料を用いるので、露
光時の副反応である架橋反応が発生しなくなる。[Function] Since the resist pattern forming method according to the present invention uses a resist material containing a radical reaction inhibitor, crosslinking reactions, which are side reactions during exposure, do not occur.
［実施例コ 以下、この発明の一実施例を説明する。[Example code] An embodiment of this invention will be described below.
感光剤として２，３．４−トリヒドロキシベンゾフェノ
ンのナフトキノンジアジド硫酸エステルを用い、樹脂と
してｍ−クレゾール／ｐ−クレゾールのノボラックレジ
ンからなるポジ型フォトレジストを用い、その中に２．
６−ｔ−ブチルクレゾールを添加する。その添加量は数
％〜１０％が好ましい。このレジストを、所定のマスク
を介して、２５Ｏｎｍ付近の紫外光を用いて露光する。Naphthoquinonediazide sulfate of 2,3,4-trihydroxybenzophenone was used as the photosensitizer, and a positive photoresist consisting of m-cresol/p-cresol novolac resin was used as the resin.
Add 6-t-butylcresol. The amount added is preferably from several % to 10%. This resist is exposed to ultraviolet light around 25 Onm through a predetermined mask.
その後、現像により所定のレジストパターンを得る。以
上の方法によりレジストパターンを形成すると、紫外光
露光時に発生する、感光剤または樹脂のラジカルは２．
６−ｔ−ブチルクレゾールに捕捉される。その結果、感
光剤または樹脂は安定化され、架橋反応が起こらない。Thereafter, a predetermined resist pattern is obtained by development. When a resist pattern is formed by the above method, the radicals of the photosensitive agent or resin generated during exposure to ultraviolet light are 2.
Captured by 6-t-butylcresol. As a result, the photosensitizer or resin is stabilized and no crosslinking reaction occurs.
第１図は、本発明における、露光後のレジストの現像液
に対する溶解速度を露光エネルギに対してプロットした
ものである。FIG. 1 is a plot of the dissolution rate of the exposed resist in the developer against the exposure energy in the present invention.
図より明らかなように、露光量が増すに従って、溶解速
度は単調に増加する。したがって、現像の際、露光部の
レジストが残渣として残るということはない。これによ
り、高精度なレジストパターンを得ることができる。As is clear from the figure, as the exposure amount increases, the dissolution rate increases monotonically. Therefore, during development, the resist in the exposed area does not remain as a residue. Thereby, a highly accurate resist pattern can be obtained.
なお、上記実施例では、レジスト感光基として、２、
３．４−トリヒドロキシベンゾフェノンのナフトキノン
ジアジド硫酸エステルを例示したが、他のキノンジアジ
ド系感光剤等でもよい。In addition, in the above example, as the resist photosensitive group, 2,
Although the naphthoquinone diazide sulfate ester of 3.4-trihydroxybenzophenone is exemplified, other quinone diazide photosensitizers may be used.
また、上記実施例ではレジスト樹脂として、ｍ−クレゾ
ール、ｐ−クレゾールのノボラック樹脂を例示したが、
他のフェノール系樹脂等のアルカリ可溶な樹脂であって
もよい。In addition, in the above examples, novolac resins such as m-cresol and p-cresol were exemplified as resist resins, but
Alkali-soluble resins such as other phenolic resins may also be used.
さらに、感光剤が樹脂中に直接に結合されているものを
使用しても、実施例と同様の効果を実現する。Furthermore, even if a resin in which the photosensitive agent is directly bonded to the resin is used, the same effect as in the example can be achieved.
また、上記実施例ではラジカル反応禁旧剤として、２．
６−ｔ−ブチルクレゾールを例示したが、この発明はこ
れに限られるものでなく、ベンゾフェノン系、フェノー
ル系、アリルアミン系等のポリマー安定剤であっても実
施例と同様の効果を実現する。In addition, in the above examples, as a radical reaction inhibiting agent, 2.
Although 6-t-butylcresol is used as an example, the present invention is not limited thereto, and the same effects as in the examples can be achieved even with polymer stabilizers such as benzophenone, phenol, and allylamine.
［発明の効果］
以上説明したとおり、この発明に係るレジストパターン
形成方法によれば、ポジ型レジスト材料に、ラジカル反
応禁止剤を添加して行なうようにしたので、露光時の副
反応である架橋反応が発生するのを防ぐことができる。[Effects of the Invention] As explained above, according to the resist pattern forming method according to the present invention, a radical reaction inhibitor is added to the positive resist material, so crosslinking, which is a side reaction during exposure, is prevented. reactions can be prevented from occurring.
結果として、露光部のレジストは完全に溶解し去り、残
渣として残らなくなり、高精度のレジストパターンを与
える。As a result, the resist in the exposed area is completely dissolved and no residue remains, providing a highly accurate resist pattern.
第１図は本発明を使用した場合の、露光エネルギと感光
後のレジストの溶解速度との関係図、第２図は従来の方
法を採用した場合の、露光エネルギと感光後のレジスト
の溶解速度との関係図である。Figure 1 is a diagram showing the relationship between exposure energy and the dissolution rate of the resist after exposure when using the present invention, and Figure 2 is a diagram showing the relationship between the exposure energy and the rate of dissolution of the resist after exposure when using the conventional method. This is a relationship diagram.
Claims (1)
て露光後、現像によって所定のレジストパターンを得る
レジストパターン形成方法において、前記ポジ型レジス
ト材料に、ラジカル反応禁止剤を添加して行なうことを
特徴とするレジストパターン形成方法。In a resist pattern forming method in which a positive resist material is applied onto a substrate, exposed through a mask, and then developed to obtain a predetermined resist pattern, a radical reaction inhibitor is added to the positive resist material. Characteristic resist pattern formation method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62291350A JPH01133045A (en) | 1987-11-17 | 1987-11-17 | Resist pattern forming method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62291350A JPH01133045A (en) | 1987-11-17 | 1987-11-17 | Resist pattern forming method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01133045A true JPH01133045A (en) | 1989-05-25 |
Family
ID=17767788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62291350A Pending JPH01133045A (en) | 1987-11-17 | 1987-11-17 | Resist pattern forming method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01133045A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5031904A (en) * | 1973-07-26 | 1975-03-28 | ||
| JPS57155534A (en) * | 1981-02-20 | 1982-09-25 | Polychrome Corp | Positively working radiation sensitive composition containing no silver |
| JPS602945A (en) * | 1983-06-21 | 1985-01-09 | Mitsubishi Chem Ind Ltd | Photopolymerizable composition |
-
1987
- 1987-11-17 JP JP62291350A patent/JPH01133045A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5031904A (en) * | 1973-07-26 | 1975-03-28 | ||
| JPS57155534A (en) * | 1981-02-20 | 1982-09-25 | Polychrome Corp | Positively working radiation sensitive composition containing no silver |
| JPS602945A (en) * | 1983-06-21 | 1985-01-09 | Mitsubishi Chem Ind Ltd | Photopolymerizable composition |
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