JPS6377053A - Pattern forming material - Google Patents
Pattern forming materialInfo
- Publication number
- JPS6377053A JPS6377053A JP22090086A JP22090086A JPS6377053A JP S6377053 A JPS6377053 A JP S6377053A JP 22090086 A JP22090086 A JP 22090086A JP 22090086 A JP22090086 A JP 22090086A JP S6377053 A JPS6377053 A JP S6377053A
- Authority
- JP
- Japan
- Prior art keywords
- resolution
- copolymer
- resist
- forming material
- trimethylsilylmethyl methacrylate
- 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
- 239000000463 material Substances 0.000 title claims abstract description 10
- 229920001577 copolymer Polymers 0.000 claims abstract description 9
- VGOXVARSERTCRY-UHFFFAOYSA-N trimethylsilylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC[Si](C)(C)C VGOXVARSERTCRY-UHFFFAOYSA-N 0.000 claims abstract description 7
- UAIFZYSPVVBOPN-UHFFFAOYSA-N trimethyl(prop-1-en-2-yloxy)silane Chemical compound CC(=C)O[Si](C)(C)C UAIFZYSPVVBOPN-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 7
- 239000001301 oxygen Substances 0.000 abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 abstract description 7
- 230000035945 sensitivity Effects 0.000 abstract description 7
- 230000002542 deteriorative effect Effects 0.000 abstract description 3
- 239000000470 constituent Substances 0.000 abstract 2
- YKPHTSHERCDMCL-UHFFFAOYSA-N trimethyl(prop-1-enoxy)silane Chemical compound CC=CO[Si](C)(C)C YKPHTSHERCDMCL-UHFFFAOYSA-N 0.000 abstract 2
- -1 poly(trimethylsilylmethyl methacrylate) Polymers 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 5
- 239000000178 monomer Substances 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
- G03F7/0758—Macromolecular compounds containing Si-O, Si-C or Si-N bonds with silicon- containing groups in the side chains
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、パターン形成材料に関し、更に詳しくは電子
線用二層構造レジストにおいて、上層レジストへの適用
が可能であり、成膜時の膜割れを解決することのできる
成Ｈ々性のよいパターン形成材料に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a pattern forming material, and more specifically, in a two-layer structure resist for electron beams, it can be applied to the upper layer resist and The present invention relates to a pattern forming material with good growth properties that can solve cracks.
近年、ＬＳＩの高密度化に呼応して、微細パターンの作
製に二層構造レジストを適用しようとする動きがある。In recent years, in response to the increase in the density of LSIs, there has been a movement to apply a two-layer resist to the production of fine patterns.
このレジストは上層および下層レジストから構成され、
通常下層レジストの膜厚は１〜３μｍ程度、上層レジス
トの膜厚は０．１〜０．５μｍ程度である。二層構造レ
ジストの特性は上層レジストの特性により大きく左右さ
れるのであるけれども、二層レジストは高感度、高解像
性、高耐酸素プラズマ性であるのが好ましい。This resist consists of an upper layer and a lower layer resist,
Usually, the thickness of the lower resist layer is about 1 to 3 μm, and the thickness of the upper resist layer is about 0.1 to 0.5 μm. Although the properties of the two-layer resist are largely influenced by the properties of the upper resist, the two-layer resist preferably has high sensitivity, high resolution, and high oxygen plasma resistance.
ポジ型二層構造レジスト用上層レジストとして、ポリ
（トリメチルシリルメチルメタクリレート）が有用であ
ることは、従来から知られていた。しかし、ポリ （ト
リメチルシリルメチルメタクリレート）からなるレジス
トは、上記３特性に優れるが、成膜性におとり、０．５
μｍ以下の膜厚になるように、例えば、シリコンウェハ
ー上に塗布すると、膜面の凹凸やひび割れが生じて、上
層レジストとしての使用が難しくなるという欠点を有す
る。Polymer is used as an upper layer resist for positive two-layer resist.
It has been known for a long time that (trimethylsilylmethyl methacrylate) is useful. However, although resists made of poly(trimethylsilylmethyl methacrylate) are excellent in the above three properties, they have a poor film formability and a
If it is coated onto a silicon wafer, for example, to a thickness of less than μm, it has the disadvantage that the film surface becomes uneven and cracked, making it difficult to use it as an upper layer resist.
ポリ （トリメチルシリルメチルメタクリレート）をポ
ジ型二層構造レジストの上層レジストに適用しようとす
る場合、従来、感度、解像度、耐酸素プラズマ性等の特
性にのみ関心が向けられ、成膜性については何らの検討
もなされていない。しかしながら、本発明者らがポリ
（トリメチルシリルメチルメタクリレート）をポジ型二
層構造レジストの上層レジストに適用してみたところ、
ポリ（トリメチルシリルメチルメタクリレート）は成膜
性に問題があること、即ち膜面に凹凸があったり、キズ
が生じたりしていることがわかった。When trying to apply poly(trimethylsilylmethyl methacrylate) to the upper layer of a positive two-layer resist, conventionally only the sensitivity, resolution, oxygen plasma resistance, etc. were the focus of attention, and film formability was not considered at all. No consideration has been given. However, the inventors
(Trimethylsilylmethyl methacrylate) was applied to the upper layer of a positive two-layer resist.
It has been found that poly(trimethylsilylmethyl methacrylate) has problems with film forming properties, that is, the film surface has unevenness and scratches.
このため、レジストとしての特性を劣化させることなく
、ポリ （トリメチルシリルメチルメタクリレート）系
重合体の成膜性を改良する必要がある。即ち、本発明は
、レジストとしてのポリ （トリメチルシリルメチルメ
タクリレート）樹脂の優れた感度、解像度および耐酸素
プラズマ性を維持したまま、成膜性を改良しようという
ものである。Therefore, it is necessary to improve the film-forming properties of poly(trimethylsilylmethyl methacrylate) polymers without deteriorating their properties as resists. That is, the present invention aims to improve the film forming properties of poly(trimethylsilylmethyl methacrylate) resin as a resist while maintaining its excellent sensitivity, resolution, and oxygen plasma resistance.
本発明によれば、下記式で示されるトリメチルシリルメ
チルメタクリレート（Ａ）とイソプロペノキシトリメチ
ルシラン（Ｂ）との共重合体からなるパターン形成材料
が提供される。According to the present invention, a pattern forming material made of a copolymer of trimethylsilylmethyl methacrylate (A) and isopropenoxytrimethylsilane (B) represented by the following formula is provided.
本発明のパターン形成材料においては、上記共重合体は
七ツマ−（Ａ）６０〜９５モル％とモノマー（Ｂ）５〜
４０モル％との共重合体であるのが好ましい。モノマー
（Ａ）とモノマー（Ｂ）との共重合は通常の方法で実施
することができる。In the pattern-forming material of the present invention, the copolymer contains 60 to 95 mol% of the monomer (A) and 5 to 95 mol% of the monomer (B).
Preferably, it is a copolymer with 40 mol%. Copolymerization of monomer (A) and monomer (B) can be carried out by a conventional method.
得られるコポリマーは、１０，０００〜５００，０００
の重量平均分子量を有するのが好ましい。The resulting copolymer has a molecular weight of 10,000 to 500,000
The weight average molecular weight is preferably .
本発明のパターン形成材料は、即ち、ポリ （トリメチ
ルシリルメチルメタクリレート）の高感度、高解像性、
高耐酸素プラズマ性を劣化させることなく、特に上層レ
ジストとして必要不可欠な特性である耐酸素プラズマ性
を劣化させることな（、成膜性を向上させるためイソプ
ロペノキシトリメチルシラン（Ｂ）を共重合させて得ら
れるコポリマーに基づくものである。The pattern forming material of the present invention is made of poly(trimethylsilylmethyl methacrylate) with high sensitivity, high resolution,
Copolymerization of isopropenoxytrimethylsilane (B) to improve film formability without deteriorating high oxygen plasma resistance, especially oxygen plasma resistance, which is an essential property for upper layer resists. It is based on a copolymer obtained by
本発明に係るパターン形成材料は、基板に対して、通常
の方法で適用することができ、また通常の方法で処理す
ることができる。The patterning material according to the invention can be applied to a substrate in a conventional manner and can be processed in a conventional manner.
以下、実施例により、本発明を更に説明する。 The present invention will be further explained below with reference to Examples.
三ツロフラスコに上記組成物、
トリメチルシリルメチルメタクリレート
１５．５ ｇイソプロペノキシトリメ
チルシラン １．３
ｇ７ゾビスイソプチ１にトリル
０．４ ｇベ ン セ シ
５０ｃ
ｃを仕込み、還流冷却管および窒素ガス４人管を取りつ
け、６０℃で２４時間反応させた。生成した固形物をベ
ンゼンに溶かし、メタノールで沈澱させた。さらに、沈
澱物をベンゼンに溶解させ、メタノールで沈澱させ、ポ
リマーを回収した。得られたポリマーは１５ Ｘ １０
’の平均分子量を有していた。The above composition in a Mitsuro flask, trimethylsilylmethyl methacrylate
15.5 g isopropenoxytrimethylsilane 1.3
g7 zobisisopetite 1 to tolyl
0.4 g
50c
A reflux condenser tube and a four-person nitrogen gas tube were attached, and the reaction was carried out at 60° C. for 24 hours. The resulting solid was dissolved in benzene and precipitated with methanol. Furthermore, the precipitate was dissolved in benzene, precipitated with methanol, and the polymer was recovered. The resulting polymer was 15 x 10
It had an average molecular weight of '.
このポリマーを、濃度１０重量％になるように、シクロ
ヘキサンに溶解させてレジスト溶解とし、シリコンウェ
ハー上に塗布した。この塗膜表面を電子顕微鏡により観
察した結果、均一かつ滑らかな膜面となっており、二層
構造レジストの上層レジストの膜面として適当であるこ
とがわかった。This polymer was dissolved in cyclohexane to a concentration of 10% by weight to form a resist solution, and applied onto a silicon wafer. As a result of observing the surface of this coating film using an electron microscope, it was found that the film surface was uniform and smooth, and it was found to be suitable as the film surface of the upper layer resist of a two-layer structure resist.
また、レジスト特性を測定したところ、感度は６−３＃
Ｃ／ｃａｌ、解像度０．５ ｐ ｍライン＆スペースで
あった。Also, when we measured the resist characteristics, the sensitivity was 6-3#.
C/cal, resolution 0.5 pm line and space.
本発明によれば、ポリ （トリメチルシリルメチルメタ
クリレート）の成膜性を改良し、しかも解像度を悪化さ
せることのないパターン形成材料を提供することができ
るので、欠点がなく、高解像度のパターンを形成するこ
とができる。According to the present invention, it is possible to provide a pattern forming material that improves the film forming properties of poly(trimethylsilylmethyl methacrylate) and does not deteriorate the resolution, so that it is possible to form a pattern with no defects and high resolution. be able to.
Claims (1)
レート（Ａ）とイソプロペノキシトリメチルシラン（Ｂ
）との共重合体からなるパターン形成材料。 ▲数式、化学式、表等があります▼（Ａ） ▲数式、化学式、表等があります▼（Ｂ）[Claims] 1. Trimethylsilylmethyl methacrylate (A) and isopropenoxytrimethylsilane (B) represented by the following formula.
) pattern-forming material consisting of a copolymer with ▲There are mathematical formulas, chemical formulas, tables, etc.▼(A) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(B)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22090086A JPS6377053A (en) | 1986-09-20 | 1986-09-20 | Pattern forming material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22090086A JPS6377053A (en) | 1986-09-20 | 1986-09-20 | Pattern forming material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6377053A true JPS6377053A (en) | 1988-04-07 |
Family
ID=16758290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22090086A Pending JPS6377053A (en) | 1986-09-20 | 1986-09-20 | Pattern forming material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6377053A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7806169B2 (en) | 2004-02-10 | 2010-10-05 | Jms Co., Ltd. | Heat exchanger, method for manufacturing the same, and heart-lung machine |
| JP2017014157A (en) * | 2015-07-02 | 2017-01-19 | 信越化学工業株式会社 | Polymerizable monomer and polymer thereof |
-
1986
- 1986-09-20 JP JP22090086A patent/JPS6377053A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7806169B2 (en) | 2004-02-10 | 2010-10-05 | Jms Co., Ltd. | Heat exchanger, method for manufacturing the same, and heart-lung machine |
| JP2017014157A (en) * | 2015-07-02 | 2017-01-19 | 信越化学工業株式会社 | Polymerizable monomer and polymer thereof |
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