JPH0235455A - Resist material and pattern forming method - Google Patents
Resist material and pattern forming methodInfo
- Publication number
- JPH0235455A JPH0235455A JP63187451A JP18745188A JPH0235455A JP H0235455 A JPH0235455 A JP H0235455A JP 63187451 A JP63187451 A JP 63187451A JP 18745188 A JP18745188 A JP 18745188A JP H0235455 A JPH0235455 A JP H0235455A
- Authority
- JP
- Japan
- Prior art keywords
- resist
- resist material
- pattern forming
- line
- forming method
- 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 19
- 238000000034 method Methods 0.000 title claims description 13
- -1 azido compound Chemical class 0.000 claims abstract description 11
- 229920002050 silicone resin Polymers 0.000 claims abstract description 7
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 2
- 230000035945 sensitivity Effects 0.000 abstract description 10
- 229920002554 vinyl polymer Polymers 0.000 abstract description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 4
- MLIWQXBKMZNZNF-UHFFFAOYSA-N 2,6-bis[(4-azidophenyl)methylidene]-4-methylcyclohexan-1-one Chemical compound O=C1C(=CC=2C=CC(=CC=2)N=[N+]=[N-])CC(C)CC1=CC1=CC=C(N=[N+]=[N-])C=C1 MLIWQXBKMZNZNF-UHFFFAOYSA-N 0.000 abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
- 239000001301 oxygen Substances 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000010276 construction Methods 0.000 abstract 1
- 238000000992 sputter etching Methods 0.000 abstract 1
- 238000001020 plasma etching Methods 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000010409 thin film Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 238000001459 lithography Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000003504 photosensitizing agent Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（概要］
レジスト材料およびパターン形成方法に関し、ｉ線に対
して高い感度を示すとともに０２ＲＩＥ耐性にも優れた
レジスト材料の提供を目的とし、
一般式
（式中、Ｉｔ、、 Ｒ，はビニル アリルアクリロイル
またはメタクリロイル基、ｎはＩＯ〜１０００の整数を
示す。）
で示されるシリコーン樹脂と、７，７．８．８−テトラ
シアノキノジメタンと、アンド化合物との混合物よりな
ることを特徴とするレジスト材料。Detailed Description of the Invention (Summary) Regarding a resist material and a pattern forming method, the purpose is to provide a resist material that exhibits high sensitivity to i-rays and has excellent resistance to 02RIE. , R, is a vinyl allylacryloyl or methacryloyl group, n is an integer from IO to 1000), 7,7.8.8-tetracyanoquinodimethane, and a mixture of an and compound. A resist material characterized by:
（２）請求項１記載のレジスト材料を、２層構造レジス
トの上層レジストに用いることを特徴とするパターン形
成方法。(2) A pattern forming method characterized in that the resist material according to claim 1 is used as an upper layer resist of a two-layer structure resist.
（式中、ＲＩ＋ Ｒｚはビニル、アリルアクリロイルま
たはメタクリロイル基、ｎは１０〜ｔｏｏｏの整数を示
す。）
で示されるシリコーン樹脂と、７，７，８．８−テトラ
ンアノキノンメタンと、アジド化合物との混合物よりな
り構成する。(In the formula, RI+ Rz is a vinyl, allyl acryloyl or methacryloyl group, and n is an integer from 10 to tooo.) A silicone resin represented by the following formula, 7,7,8.8-tetraanoquinone methane, and an azide compound. It consists of a mixture of.
本発明は、レジスト材料およびパターン形成方法に関す
る。さらに詳しく説明すれば、高解像性を達成するため
に露光源にｉ線を用いた場合におけるｉ線用ネガ型レジ
スト材料、および２層レジスト法によるパターン形成方
法に関する。The present invention relates to resist materials and pattern forming methods. More specifically, the present invention relates to a negative resist material for i-line when i-line is used as an exposure source in order to achieve high resolution, and a pattern forming method using a two-layer resist method.
近年の集積回路の高集積化に伴い、回路パターンはさら
に微細化する傾向にある。現在、２５６ＫＤＲＡＭ （
タイｔミフク ラシタム アクセス メモリー） にお
ける回路パターンの最小線幅は１．２μｍであり、ポジ
型フォレジストを用いてｇ線（ｇ−１ｉｎｅ、波長４３
６ｒ＋＋ｗ）の小投影露光法により形成している。しか
し、この縮小投影露光法は、レジスト膜中に発生する定
在波や配線側面からの反射、焦点深度が浅いなどの原因
により解像性が低下するため、超微細パターンの形成に
は適さない。As integrated circuits have become more highly integrated in recent years, circuit patterns have tended to become even finer. Currently, 256KDRAM (
The minimum line width of the circuit pattern in Thai tmifucracitum access memory is 1.2 μm, and the minimum line width of the circuit pattern in the
6r++w) small projection exposure method. However, this reduction projection exposure method is not suitable for forming ultra-fine patterns because the resolution decreases due to standing waves generated in the resist film, reflections from the side of the wiring, and shallow depth of focus. .
そこで、基板上に存機物による平坦化層（下層レジスト
）を設け、該平坦化層の上に感光性高分子の薄膜（上層
レジスト）を形成する２層構造レジストとし、ｇ線を用
いて該薄膜を露光し現像してパターンを形成した後、パ
ターニングされた該薄膜をマスクに酸素ガスによる反応
性イオンエツチング（ＯｚＲＩＥ）を行って下層レジス
トにパターンを転写する方法（２層レジスト法）が採用
されている。Therefore, we created a two-layer structure resist in which a flattening layer (lower layer resist) made of existing material is provided on the substrate, and a thin film of photosensitive polymer (upper layer resist) is formed on the flattening layer. After the thin film is exposed and developed to form a pattern, reactive ion etching (OzRIE) using oxygen gas is performed using the patterned thin film as a mask to transfer the pattern to the underlying resist (two-layer resist method). It has been adopted.
この２層構造レジストにおいて、厚さ２μｍ程度の下層
レジストに対して、上層レジストは、高解像性を達成す
るために０．３〜０．５μｍと非常に薄く形成される。In this two-layer resist, the upper resist layer is formed to be very thin, 0.3 to 0.5 μm, in order to achieve high resolution, compared to the lower resist layer, which has a thickness of about 2 μm.
従って、ト層レジストとしては、０、−ＲＩＥの際に下
層レジストに対して少なくとも２０倍以上の選択比を有
する必要がある。Therefore, the upper layer resist must have a selectivity of at least 20 times or more with respect to the lower layer resist during 0,-RIE.
〔発明が解決しようとする課題］
ｇ線でのりソグラフィは、０．６μｍ設計ルールまでの
使用は可能であるが、１６Ｍ ＤＲＡＭの作成で要求さ
れる０、５μｍルールになると、光の干渉効果によりｇ
線でのりソグラフィは難しくなる。この対策として、上
層レジストの露光源にｇ線よりも波長の短いｉ線（ｉ−
目ｎｅ、波長３６５ｎｍ）を用いて、解像性の向上を図
る方法が有望視されている。しかし、従来、このｉ線に
対して高い感度を示し、かつ０□−ＲｒＥ耐性にも優れ
たレジスト材料はない。[Problem to be solved by the invention] G-line lithography can be used up to a 0.6 μm design rule, but when it comes to the 0.5 μm rule required for the creation of 16M DRAM, it becomes difficult due to light interference effects. g
Glue lithography with lines becomes difficult. As a countermeasure to this problem, the exposure source for the upper resist layer is used as an i-line (i-line), which has a shorter wavelength than the g-line.
A method of improving resolution using a wavelength of 365 nm is considered promising. However, conventionally, there is no resist material that exhibits high sensitivity to the i-line and also has excellent resistance to 0□-RrE.
そこで本発明は、ｉ線に対して高い感度を示し、さらに
０□−ＲＩＥ耐性にも優れたレジスト材料の提供、さら
にサブミクロンパターンの形成を可能とするパターン形
成方法の提供を目的とする。SUMMARY OF THE INVENTION Accordingly, the present invention aims to provide a resist material that exhibits high sensitivity to i-rays and has excellent resistance to 0□-RIE, and also to provide a pattern forming method that enables the formation of submicron patterns.
（課題を解決するための手段〕
前記目的は、一般式
本発明では、レジストの主成分であるラダー型シリコー
ン樹脂は、一般式にその構造式を示すように、その骨格
構造にＳｉを含存するので、０□ＲＴＥのときにＳｉが
酸素と反応して表面にＳｉＯ□の保ｊ［が形成され、こ
のため優れたｏ２−ＲＩＥ耐性を示す。このラダー型シ
リコーン樹脂に、感光剤としてｉ線付近の光を吸収する
アジド化合物と７．７，８．８−テトラシアキノジメタ
ンを添加することによりｉ線用ステッパで露光する際の
感度が向上する。(Means for Solving the Problems) The above object is based on the general formula of the present invention, in which the ladder-type silicone resin, which is the main component of the resist, contains Si in its skeletal structure, as shown in the structural formula in the general formula. Therefore, during 0□RTE, Si reacts with oxygen to form a bond of SiO□ on the surface, which exhibits excellent o2-RIE resistance. By adding an azide compound that absorbs nearby light and 7,7,8,8-tetracyaquinodimethane, the sensitivity during exposure with an i-line stepper is improved.
（式中、Ｒ１＋ Ｒｚはビニル、アリルアクリロイルま
たはメタクリロイル基、ｎは１０〜１０００の整数を示
す。）
で示されるシリコーン樹脂と、７．７，８．８−テトラ
シアノキノジメタンと、アジド化合物との混合物よりな
ることを特徴とするレジスト材料により達成される。(In the formula, R1+Rz is a vinyl, allyl acryloyl or methacryloyl group, and n is an integer of 10 to 1000.) A silicone resin represented by the following, 7.7,8.8-tetracyanoquinodimethane, and an azide compound This is achieved by a resist material characterized by being made of a mixture of
〔実施例］
次に本発明の実施例について説明する。ラダー型シリコ
ーン樹脂であるシリル化ポリビニルンルセスキオキサン
Ｉｇを旧ＢＫ （メチルイソブチルケトン） ９ｇに溶
解し、感光剤として２，６−ビス−（４−アジドベンザ
ル）−４−メチルシクロヘキサノン（シンコー技研５り
をＯ，ＯＩｇと、さらに構造式がで示される７、７，８
．８−テトラシアノキノジメタン（ＴＣＮＯ）を０．０
０１ｇ添加して、本発明のレジスト溶液を得た。[Example] Next, an example of the present invention will be described. Silylated polyvinyl sesquioxane Ig, which is a ladder-type silicone resin, was dissolved in 9 g of old BK (methyl isobutyl ketone), and 2,6-bis-(4-azidobenzal)-4-methylcyclohexanone (Shinko Giken 5) was used as a photosensitizer. 7, 7, 8, whose structural formula is O, OIg, and
．． 8-tetracyanoquinodimethane (TCNO) 0.0
01g was added to obtain a resist solution of the present invention.
続いて、本発明の実施例に係るパターン形成方法につい
て説明する。Ｓｉ基機上に下層レジストとしてＭＰ−１
３００（シブレー社製）を２μｍの膜厚にスピンコード
した後、２００°Ｃで１時間ハードベイクして下層レジ
ストを形成した。この下層レジスト上に前記レジスト溶
液を０．２μｍの膜厚にスピンコードした後、６０°Ｃ
で２０分間溶剤乾燥して上層レジストを形成した。この
上層レジストにｉ線用ステッパを用いて波長３６５ｎｍ
のｉ線で露光した後、旧ＢＫとＩＰＡ（イソプロピルア
ルコール）を１＝４の割合で混合した溶液に３０秒間浸
漬して現像した。Next, a pattern forming method according to an embodiment of the present invention will be described. MP-1 as lower layer resist on Si-based substrate
300 (manufactured by Sibley) to a thickness of 2 μm, and then hard-baked at 200° C. for 1 hour to form a lower resist layer. After spin-coding the resist solution on this lower resist layer to a thickness of 0.2 μm, the temperature was 60°C.
The upper layer resist was formed by solvent drying for 20 minutes. A wavelength of 365 nm was applied to this upper layer resist using an i-line stepper.
After exposure to i-line, the film was developed by immersing it in a solution of old BK and IPA (isopropyl alcohol) in a ratio of 1=4 for 30 seconds.
このとき、本実施例の上層レジストは５抛Ｊ／ｃＩｌｚ
の感度番示し、０．５μｍのラインアンドスペース（Ｌ
ｉｎｅ ＆ ５ｐａｃｅ ）で解像した。この後、０□
−ＲＩＥにより上層レジストのパターンを下層レジスト
に転写したところ、上層レジストがＩＰｉＭすすること
なく、また、パ゛ターン幅のシフトも起きることなく転
写できた。At this time, the upper layer resist of this example has a thickness of 5 J/cIlz
sensitivity number, 0.5 μm line and space (L
ine & 5 pace). After this, 0□
- When the pattern of the upper resist layer was transferred to the lower resist layer by RIE, the upper layer resist was transferred without IPiM smearing and without any shift in pattern width.
本実施例のレジストの主成分であるシリル化ポリビニル
シルセスキオキサンはＳｉ含有率が高く、このため優れ
た０ｆ−ＲＩＥ耐性を示す。さらに感光剤としてｉ線付
近の光を吸収する２、６−ビス−（４−アジドベンザル
）−４−メチルシクロヘキサノンと７．７，８．８−テ
トラシアキノジメタンを添加することによりｉ線用ステ
ッパで露光する際の感度が向上する。このように本発明
では、レジスト主成分にＳ＋樹脂を用いてＯ，−ＲＩＥ
耐性を高めるとともに、アジド化合物とＴＣＮＱを添加
することにより高感度を達成している。The silylated polyvinylsilsesquioxane, which is the main component of the resist of this example, has a high Si content and therefore exhibits excellent Of-RIE resistance. Furthermore, by adding 2,6-bis-(4-azidobenzal)-4-methylcyclohexanone and 7.7,8.8-tetracyaquinodimethane, which absorb light near the i-line, as photosensitizers, Sensitivity is improved when exposing with a stepper. In this way, in the present invention, O,-RIE is performed using S+ resin as the main component of the resist.
In addition to increasing resistance, high sensitivity is achieved by adding an azide compound and TCNQ.
この結果、ｉ線に対して高感度、かつＯ□ＲＩＢ耐性に
も優れたレジスート材料が堤供されるようになり、この
レジスト材料を２層構造レジストの上層レジスト材料と
し、ｉ線用ステッパで露光することにより、超微細なパ
ターンが解像性良く形成できるようになる。従って、集
積回路のより一層の微細化、高集積化に効果がある。As a result, a resist material with high sensitivity to i-line and excellent resistance to O By exposing to light, ultra-fine patterns can be formed with good resolution. Therefore, it is effective for further miniaturization and higher integration of integrated circuits.
なお、添加するアジド化合物としては、２．６−ビス−
（４−アジドヘンザル）−４−メチルシクロヘキサノン
以外を使用してもよい。他のアジド化合物の一例を下記
に示す。The azide compound to be added is 2,6-bis-
You may use substances other than (4-azidohenzal)-4-methylcyclohexanone. Examples of other azide compounds are shown below.
”’＠−Ｃ００ＣｔｌｚＮＩｌｚ
””＠−Ｃ００ＣＩｈＮＨ，Ｚ
”＠−Ｃ００ＣＨ１ＣＨ！ＮＬ
Ｎ ３ＳＯ２，、□−６゜。Ｃ１（ＺＣＩＺＮ＋（２１
◎−ＣＯＯＣＨｚＮ （ＣＨ３）２
８°３０′［有］−６゜。。１１□８．。１ｌｈ）ｚ９
゛［有］−ＣＯＯＣＩＩｚＮ（Ｃｚ）ｌ＊）ｚ”””当
−Ｃ００Ｃ）１２Ｎ（。ｚｌｈＬ１◎−ＣＯＯＣＨｚＣ
ＨｚＣＨｚＮ（ＣＨｉ）ｔ””＠ Ｃ００ＣＨｚＣｌｈ
ＣＬＮ（Ｃ１ｈ）ｚ１◎−Ｃ００ＣＨ２ＣＩＩＩＣＩＩ
ＺＮ（。ｄｌｉ）ｚ””’□−Ｃ００ＣＨｚＣＩｈＣＨ
Ｊ（。Ｊ３）！〔発明の効果〕
本発明によれば、ｉ線に対して高感度、かつ０゜ＲＩＥ
耐性にも優れたレジスト材料が提供されるようになり、
このレジスト材料を２層構造レジストの上層レジスト材
料とし、ｉ線用ステッパで露光することにより、超微細
なパターンが解像性良く形成できるようになる。この結
果、集積回路のより一層の微細化、高集積化に効果があ
る。”'@-C00CtlzNIlz ””@-C00CIhNH,Z ”@-C00CH1CH! NL N 3SO2,, □-6°. C1(ZCIZN+(21
◎-COOCHzN (CH3)2 8°30' [Yes] -6°. . 11□8. . 1lh)z9
゛[Yes]-COOCIIzN(Cz)l*)z"""This-C00C)12N(.zlhL1◎-COOCHzC
HzCHzN(CHi)t””@ C00CHzClh
CLN(C1h)z1◎-C00CH2CIIICII
ZN(.dli)z""'□-C00CHzCIhCH
J(.J3)! [Effects of the Invention] According to the present invention, high sensitivity to i-line and 0° RIE
Resist materials with excellent resistance are now available,
By using this resist material as an upper layer resist material of a two-layer structure resist and exposing it with an i-line stepper, an ultra-fine pattern can be formed with good resolution. As a result, it is effective for further miniaturization and higher integration of integrated circuits.
なお、ｉ線用ステッパとしては、従来のｇ線用ステッパ
が流用できるので、設備投資が少なくて済むことも見逃
せない。It should be noted that a conventional g-line stepper can be used as the i-line stepper, so it should not be overlooked that equipment investment can be reduced.
Claims (2)
ルまたはメタクリロイル基、 ｎは１０〜１０００の整数を示す。） で示されるシリコーン樹脂と、７，７，８，８−テトラ
シアノキノジメタンと、アジド化合物との混合物よりな
ることを特徴とするレジスト材料。(1) A silicone resin represented by the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. A resist material comprising a mixture of 7,7,8,8-tetracyanoquinodimethane and an azide compound.
トの上層レジストに用いることを特徴とするパターン形
成方法。(2) A pattern forming method characterized in that the resist material according to claim 1 is used as an upper layer resist of a two-layer structure resist.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63187451A JPH0235455A (en) | 1988-07-26 | 1988-07-26 | Resist material and pattern forming method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63187451A JPH0235455A (en) | 1988-07-26 | 1988-07-26 | Resist material and pattern forming method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0235455A true JPH0235455A (en) | 1990-02-06 |
Family
ID=16206307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63187451A Pending JPH0235455A (en) | 1988-07-26 | 1988-07-26 | Resist material and pattern forming method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0235455A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10319597A (en) * | 1997-05-23 | 1998-12-04 | Mitsubishi Electric Corp | Photosensitive silicone ladder polymer composition and method for transferring pattern to this composition and semiconductor device using this composition |
| KR100760522B1 (en) * | 2006-09-28 | 2007-10-04 | 제일모직주식회사 | Hardmask composition coated under photoresist and process of producing integrated circuit devices using thereof |
| JP2009166492A (en) * | 2007-12-19 | 2009-07-30 | Canon Inc | Manufacturing process of liquid discharge head |
-
1988
- 1988-07-26 JP JP63187451A patent/JPH0235455A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10319597A (en) * | 1997-05-23 | 1998-12-04 | Mitsubishi Electric Corp | Photosensitive silicone ladder polymer composition and method for transferring pattern to this composition and semiconductor device using this composition |
| KR100760522B1 (en) * | 2006-09-28 | 2007-10-04 | 제일모직주식회사 | Hardmask composition coated under photoresist and process of producing integrated circuit devices using thereof |
| WO2008038863A1 (en) * | 2006-09-28 | 2008-04-03 | Cheil Industries Inc. | Novel organosilane polymer, hardmask composition for resist underlayer film comprising the organosilane polymer, and process of producing semiconductor integrated circuit device using the hardmask composition |
| JP2009166492A (en) * | 2007-12-19 | 2009-07-30 | Canon Inc | Manufacturing process of liquid discharge head |
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